The Ultimate 7-Day New England Fall Road Trip Itinerary (With Map)

New England is one of the most beautiful places in the country in the fall. The coasts of Massachusetts and Maine have rocky shorelines, white lighthouses, and working harbors full of lobster boats. A few hours inland, the White Mountains and the hills of Vermont literally explode into the most gorgeous reds and oranges and golds you’ve ever seen.

We did both in one week, and this guide shows you how.

You’ll get our full seven-day New England fall road trip itinerary, a custom map with every stop pinned, where we stayed, where we ate (I was on a serious mission to find the best lobster roll in New England, and I took that very seriously), and the tips that made our days smoother. 

My 85 year old dad had never been to Vermont or New Hampshire so of course we brought him along to check those states off his travel bucket list. So, I’ve included some tips on accessibility too. 

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New England Fall Road Trip Map

Every stop in this itinerary is pinned right here, organized by day and color-coded so you can see the whole route at a glance. Click any pin to see the spot’s name and details, or use the menu in the top-left corner to turn each day’s layer on and off. You can zoom, scroll, and explore the full loop from coast to mountains and back.

Bookmark this post so you can see the map (and the entire itinerary) will be just a tap away when you need it.

When Is the Best Time for A Fall New England Road Trip?

The short answer for when to catch New England’s fall foliage is early October. The real answer is it depends. I know, not a very helpful answer right? Bear with me.

Historically, the White Mountains start showing off in late September and colors peak the first or second week of October. Cape Ann and the coast of Maine don’t hit their stride until mid-to-late October. 

However, weather conditions affect when the colors reach their brightest. You can get a good idea of how the colors will change on the Explore Fall foliage map. I’ve used it for years to track the fall foliage where we live. They update the map daily and I’ve found it to be pretty accurate.

Just remember that the closer you get to peak season, the more crowded it’s going to be. We’re talking 3 to 4 million people flooding into Vermont and New Hampshire during a few short weeks, all squeezing into adorable little towns that were not built for those types of crowds.

Shoulder Season for Fall Foliage: Early to Mid-September

Colors start to turn in the higher elevations and the crowds have not descended yet so it’s easier to find deals on hotel rooms during shoulder season. As someone who does not like elbowing my way through large masses of humanity, I love a shoulder season. That’s when we plan most of our trips.

The trade off for avoiding the crowds is that some spots may not be fully open for the season. Several restaurants in Stowe were only open for dinner. Finding open lunch spots was challenging on a couple of days. Locals told us they opened for the season on October 1.

Peak Season for Fall Foliage: Late September to Mid-October

Peak season is when the fall colors are absolutely exploding. I’m talking those “I can’t believe my eyes” types of colors. But of course those gorgeous colors bring the crowds.

If peak season is your goal, book early. Hotels, tours and even rental cars will sell out weeks (if not months) in advance.

Our Trip Timing

We took our trip during my school’s fall break (September 20 – 28), so we were straddling shoulder and peak seasons. We expected to see modest, early-season color.

We started with the coastal leg of our trip so Vermont and New Hampshire had a little more time to develop their fall foliage colors. Vermont’s drought that year meant the leaves turned earlier and we ended up seeing an absolute explosion of gorgeous colors by the end of the week.

Where to Start a New England Fall Road Trip

This itinerary kicks off in Salem, Massachusetts, so unless you are within driving distance, fly into Boston Logan Airport. With traffic, Salem is only a 30-40 minute drive from the airport.

Pro Tip: The car rental center at Logan is off-site, but easy to get to. Follow the signs to Ground Transportation and look for the blue shuttle buses. Bus numbers 22, 33, and 55 will all get you to the rental center in about 15 minutes. 

Just remember to tack that 15 minutes onto both ends of your trip, because nothing wrecks a travel day like sprinting through Logan because you forgot to budget time for the shuttle on the way home.

Day 1: Travel Day to Boston & Drive to Salem

Travel days can be loooooonnnng and exhausting so how much you do once you land in Boston will depend on what time you land and how much energy you have left. I’ve got options for you.

Option 1: Explore Salem After Dark

Salem celebrates Halloween the way New Orleans celebrates Mardi Gras…for weeks. Starting in mid-September, the town is decorated to the hilt, costumed characters roam the streets, and everyone’s in a party mood.

For a fun, adults only night out I recommend the Salem Booze and Brews Haunted Pub Crawl because history is always more interesting after a cocktail or two. We did this one with our daughter and son-in-law on an earlier trip to Salem and had the best time!

A Salem History Tour after dark still has the spooky stories but it’s something the whole family can do together. We braved the History Tour after dark on our first trip to Salem with our kids. I say “braved” because it was the end of December and a bone-chilling 25°. Despite the late hour and freezing temps our kids all said that it was their favorite part of our entire trip.

Option 2: Dinner and an Early Night

We landed in the afternoon with big plans for Option 1. I really wanted to see Salem after the sun went down. But my dad’s flight was delayed until almost 7:00. After waiting in the airport for an extra three hours, we were not feeling very festive.

We picked up takeout from Craft Kitchen & Bar in Danvers on the way to our hotel and called it a night. Side note: dinner was so good! Jason’s pizza and dad’s wings both got high reviews from the guys. And I kicked off my coastal New England road trip with their lobster grilled cheese. It. Was. Delicious.

Option 3: Spend the First Night in Boston

A day is enough time for you to see a few of the iconic sights in one of our favorite cities.

The Freedom Trail can be walked in 2-3 hours or stretched into 5-6 hours with stops and photo ops. Download the GuideAlong audio tour to help make the most of your time. We’ve used GuideAlong tours in New England, Banff, and driving up Pikes Peak. The tours are packed full of information and are honest about you what to see and what to skip. We love these tours.

Another option is to eat your way through Boston on a foodie walking tour. What could be better than touring the North End, the Freedom Trail, and Beacon Hill while indulging in delicious food?

My personal favorite tour we have done in Boston is the Boston Harbor Sunset Sail Tour . The skyline from the water is absolutely stunning and it’s such a relaxing way to end the day.

Pro Tip: Avoid the stress of driving downtown and take a rideshare into the city. Pick up your rental in the morning and use the cash you’ll save on parking for a lobster roll at James Hook & Co.

🏨 Check out my full guide to where to stay in Boston, with all the best hotels broken down by neighborhood.

Where to Stay in Salem

Dad used Marriott points to book a two-bedroom suite at the Residence Inn Boston North Shore in Danvers. While not fancy, it was close to Salem, the suite gave us room to spread out, and it included breakfast so we could get an early start the next morning.

Day 2: Explore Cape Ann

Today you’ll work your way up the gorgeous coast, starting in Salem, rolling through Manchester-by-the-Sea and Gloucester, and landing in Portsmouth, New Hampshire by nightfall.

It’s the longest driving day of the trip, so the earlier you start, the more sights you’ll be able to fit in. If you’re on the road by 8:00 am you should have no problem reaching Portsmouth in time to catch the sunset over an iconic lighthouse. Not an early riser? Pick your two or three must-dos and let the rest go.

Morning: Explore Salem

If you need a caffeine jump start, head to Blackcraft Coffee. It’s a spooky little cafe tucked in the back corner of the Blackcraft store on Essex Street and a fun, only-in-Salem type of coffee shop.

Pro Tip: Blackcraft Coffee requires reservations from mid-September through mid-November, even for grab-and-go coffee. They release the reservation slots in late summer, so get on their email list if you want to secure your spot.

You’ve only got a morning here, so if you want to see the most of Salem in the least time, take a tour. A good guide packs the history and highlights into a couple of hours, which is perfect when you have a long day of exploring ahead. I’ve got three very different options for you:

1692 Salem Day Tour | 4.9 ⭐️ | For the real history behind the witch trials and not the jump-scare version, this is your tour. A Salem native walks you through 400 years of the city’s story in two hours.

Salem Through a New Lens Tour | 5.0 ⭐️ | This one’s a two-for-one. You’ll dig into the 1830 murder of Captain Joseph White, while a professional photographer teaches you how to frame better shots. Bring a DSLR or just your phone. (Don’t forget a power bank)

Merchants & Mansions Architecture Tour | 5.0 ⭐️ | Your guide walks you through the McIntire District, telling the stories behind grand sea-captain mansions, the Ropes Mansion, and the Witch House across three centuries of architecture.

Prefer to explore on your own? Downtown Salem is compact and walkable, centered on the Essex Street pedestrian mall, a brick-and-cobblestone stretch closed to traffic and lined with shops, cafes, and historic sites. Wander the side streets, head to the waterfront, and you’ll hit most of the highlights before lunch.

Afternoon: Manchester By The Sea, Gloucester, and Rockport

Leaving Salem, set your GPS to follow MA-127 up the coast toward Gloucester. There’s a faster inland route, but MA-127 hugs the shoreline and the views are worth the few extra minutes.

You’ll pass through Manchester-by-the-Sea on the way, an adorable little seaside town worth a quick stop if you have time. Wander the small downtown, or swing by the famous Singing Beach and see if you can get the sand to “sing” as you walk across it.

Hammond Castle

Just up the coast in Gloucester, is a medieval-style castle set on a cliff overlooking the water that you have to see to believe. Built by John Hays Hammond Jr, an inventor so eccentric he could have walked straight out of a movie.

After falling in love with European castles as a kid, he built his own version in the 1920s and filled it with authentic medieval and Renaissance pieces he collected on his travels.

Hammond held over 800 patents (including inventions that led to modern day drone technology), so he was obviously brilliant. He was also a mischievous practical joker with a slightly wicked sense of humor. The house is full of little surprises and oddities designed purely to get a reaction out of his dinner guests. I won’t spoil them here, they’re too good.

With lots of steps and narrow spiral staircases, the castle is not ADA accessible. My dad sat this one out and rested in the car while we explored. Give yourself about 45 minutes inside. 

Gloucester

Your next stop is Gloucester, the oldest seaport in the country and still one of the most active. This is a working fishing port, salty and a little gritty. You may know it as the home of the Andrea Gail, the fishing boat lost at sea in the book and movie The Perfect Storm.

If you want to spend a little time here, here’s what I’d recommend:

Walk Stacy Boulevard. This waterfront walkway is lined with flower beds and harbor views, and it’s home to two of Gloucester’s most famous landmarks: the Fisherman’s Memorial, the “Man at the Wheel” statue honoring the thousands of local fishermen lost at sea, and the Fishermen’s Wives Memorial, honoring the women and children who waited for them to come home.

Explore Rocky Neck. One of the oldest working art colonies in the country, this small waterfront peninsula is where Winslow Homer and Edward Hopper once painted. Today you can wander the galleries and studios, buy original work straight from the artists, and see the same harbor views that inspired them.

Whale Watching (Save for Later): Gloucester is also one of the best places on the East Coast to go whale watching. Unfortunately the trips run about four hours, so it doesn’t fit into this already-packed day. But if you’ve got an extra day on Cape Ann, or you’re building a separate trip to the area, it’s worth planning a morning around. We’d book the 7 Seas Whale Watch, which guarantees sightings and leaves right from the Gloucester waterfront.

Lunch at Blue Collar Lobster Co

Now for lunch. And y’all. I mean. Y’aaaalll. If you like seafood you’ re going to want to go to Blue Collar Lobster Co. Order at the window, grab a table outside and wait to be buzzed. The seafood is fresh. The portions are huge. And the people are insanely nice.

My lobster roll was the biggest I had the entire trip (and trust me, I had a lot of them). It was easily the best food value of the week. Jason and my dad both got the haddock and said it was just as incredible.

Keep an eye out, the Wicked Tuna boats run out of this harbor, so if you’re a fan, you might just spot one heading out or coming back in for the day.

Eastern Point Lighthouse

Your last stop in Gloucester is Eastern Point Lighthouse, the first of many classic lighthouses you’ll see on the coastal stretch of your New England fall road trip.

The lighthouse itself is fenced off and owned by the Coast Guard, so you can’t walk right up to it, but you can absolutely drive out and park at the point. There’s a $10 parking fee, so bring cash.

You can see the lighthouse from the parking lot, so if you just want the photo, you can get that without going any farther. But if you have time, walk down toward the water and follow the fence line out to the Dog Bar Breakwater, a long stone jetty running out into the harbor. The views looking back toward the point are stunning and it’s a great spot for pictures.

Rockport

From Eastern Point, it’s a short drive up to Rockport, the quintessential Cape Ann fishing village at the tip of the cape. We’d visited back in June with our daughter and son-in-law and loved it so much we wanted my dad to see it too.

Head straight to Bearskin Neck, a narrow peninsula packed with galleries, shops, and seafood shacks. Look for Motif Number One, the little red fishing shack on the wharf that’s said to be the most-painted building in America. If it looks familiar that’s because Rockport stood in for Sitka, Alaska in the Sandra Bullock and Ryan Reynolds movie The Proposal.

We loved Rockport enough that it’s earned its own guides here. For everything to see, eat, and do, read my full post on things to do in Rockport. And if you’d rather make it an overnight, here’s where to stay in Rockport.

➡ READ NEXT: Where to Stay in Rockport, Massachusetts ⬅

Evening: Explore Portsmouth

By the time you reach Portsmouth, you’ve put in a long day, so how you spend the evening comes down to your energy and what time you roll in.

Things to Do in Portsmouth

Portsmouth is a walkable, historic seaport with plenty to fill an afternoon or early evening if you’ve got the daylight: Strawbery Banke Museum (an outdoor living-history village), Market Square (the downtown hub of shops and cafes), Prescott Park along the waterfront, the Governor John Langdon House, and the USS Albacore, a research submarine open for tours.

Check current hours before you go, since a few are seasonal and several close by late afternoon, and pick whatever fits your arrival and your group.

Water View Grill was our dinner plan, but after that Blue Collar lobster roll, none of us could even think about a full meal. So we’re saving it for you to try.

Portsmouth Harbor Lighthouse

End your day chasing the sunset at Portsmouth Harbor Lighthouse. The walkway out to the lighthouse was washed away in a storm a few years back, so the best spot for pictures is Great Island Common in New Castle. This big waterfront park has a great view down the beach to the lighthouse.

A note for my fellow photographers: The sun sets behind you here, not behind the lighthouse, so you won’t get those fiery sunset-behind-the-lighthouse shots. What you will get is gorgeous golden-hour light, with the lighthouse glowing in that soft light. Time your arrival for a little before sunset, around 6:45 in late September and earlier as fall goes on. Check the exact sunset time for the day you’re visiting.

Parking was free and the lawn was full of locals out enjoying the evening. After taking too many pictures, we grabbed a bottle of wine, headed back to the room, and rested up for the next day.

Where To Stay in Portsmouth

Using Marriott points again, we booked the Fairfield Inn Portsmouth Seacoast. It sits just off the highway, which made for a quick in-and-out on a night we rolled in late and left early.

Day 3: Explore the Coast of Maine to Portland

Today you wave goodbye to New Hampshire and cruise up the gorgeous Maine coast to Portland, with a couple of stops along the way that surprised us and became trip favorites. After yesterday’s marathon, this is a much more relaxed driving day, so you can take your time.

Traveling with a disability placard? New Hampshire, Maine, and Vermont all let vehicles with a disability placard or plate park free at public meters and on-street spaces, and all three honor out-of-state tags, so your home placard works.

Morning: Breakfast & Lighthouse Hopping Up the Coast

Start your day with breakfast at The Friendly Toast in downtown Portsmouth. It’s a funky, eclectic spot with retro decor and a big, creative menu, and the food was delicious. And since I wasn’t driving, I ordered one of their seasonal mimosas that had apple moonshine, apple cider, and bubbles with a caramel cinnamon sugar rim. It was as good as it sounds. 

If you didn’t get to wander Portsmouth’s downtown last night, you’ve got a little time this morning. It’s such a cute waterfront town and worth a quick stroll before you hit the road for Maine.

Cape Neddick Lighthouse (Nubble Light)

Right after breakfast, make the quick detour to Cape Neddick Lighthouse in York, better known as Nubble Light. You’ll recognize it. It’s one of the most photographed lighthouses in the world.

The white tower and red-roofed keeper’s house sit on their own tiny rocky island just offshore, with the open Atlantic behind them. Parking is free, and there’s a small seasonal gift shop and restrooms. 

Fun fact: in 1977, a photo of Nubble Light was launched into space aboard NASA’s Voyager, chosen as one of the images to represent Earth to anyone who might find it. Not bad for a little lighthouse in Maine.

Afternoon: Ogunquit and Kennebunkport Maine

Ogunquit, Maine

I’ll be honest, I expected Ogunquit to be a quick drive-through, and it turned into one of our favorite stops of the whole trip.

Head to Perkins Cove first, and get there early. The parking lot is small and fills fast. We grabbed one of the last open spots mid-morning, and by the time we left, cars were circling like sharks waiting for someone to leave. Getting there early is the difference between a relaxing stop and a frustrating one.

Perkins Cove is an adorable working harbor turned shopping village with a cluster of galleries, gift shops, and seafood spots wrapped around a small cove with a pedestrian drawbridge connecting the sides. It’s a fun mix of souvenir shops and high end boutiques.

For you Gilmore Girls fans: Lorelai recommends Barnacle Billy’s to Luke in one episode, and it’s become a bit of a fan pilgrimage. 

Walking the Marginal Way was the highlight of our entire day. It’s a paved coastal path that winds about a mile and a quarter along the cliffs between Perkins Cove and Ogunquit Beach, with nonstop views of the Atlantic. It gets busy, but it never felt overcrowded, and there are benches and overlooks where you can stop and take in the views.

My dad did it on his mobility scooter without trouble. There are a few modest hills and some uneven patches, so it might be tougher in a manual wheelchair.

If some beach time is more your speed, Ogunquit Beach is one of the best stretches of sand in New England.

Kennebunkport

From Ogunquit, head north to Kennebunkport where you’ll have lunch. Go to The Clam Shack, a tiny takeout stand right on the bridge between Kennebunk and Kennebunkport. It’s been serving fresh seafood since 1968 and former First Lady Barbara Bush famously called its fried clams the best in the world.

Be ready to wait, but the line is honestly part of the experience. I had a great time chatting with some locals and other tourists while we waited. They loved hearing about the South and I loved all their local recommendations for places to see in Maine.

Of course I ordered a lobster roll. Are you sensing a theme? You can get the traditional Maine (served cold with mayo) or Connecticut (served warm with butter) style. Or, you can get a mix of both, which is what I ordered and loved it. The guys had the haddock and thought it was good but not as tasty as Blue Collar Lobster Co in Gloucester. (I think Day 2 spoiled them)

After lunch, walk it off in town. Kennebunkport is full of shops, restaurants, and gorgeous old homes. Drive past St. Ann’s Episcopal Church, the seaside stone church the Bush family attends. It’s only open seasonally and wasn’t open when we visited, but you can walk the grounds and see the exterior.

Then take a slow drive through the neighborhoods to gawk at the waterfront mansions, and head out to Walker’s Point to see the Bush compound. If the Texas flag is flying, a member of the family is in residence.

If you want to see a quieter side of Kennebunkport, take the short drive out to Cape Porpoise, a working fishing village where you can watch the lobster boats unload at the pier and catch a view of Goat Island Lighthouse across the water. It’s a refreshing change of pace from the touristy bustle of Dock Square.

Evening: Portland Head Light and Dinner in Portland

Portland is home base for the next two nights, and it’s a nice shift after a string of small coastal towns. For such a small city, it’s regularly ranked one of the best food cities in the country. Oh, and some of Maine’s most famous lighthouses sit right on its doorstep.

We pulled into town around 4:00 and drove straight out to Two Lights in Cape Elizabeth. Dad was done for the day after that, so we got him settled at the hotel. Jason and I had one more stop in us, though: Portland Head Light at golden hour.

Here’s a tip if you go in the evening like we did. The scenic overlooks to the right are best for morning light, but for golden hour, walk the path to the left, that’s where the lighthouse glows in that late, low sun. It was stunning.

We stayed longer than planned at Portland Head Light and missed our dinner plans. So, we picked up charcuterie and a bottle of wine on the way back to the hotel and settled in for the night.

If going out is more your speed, Scales is a Portland-classic seafood spot on the waterfront, and Central Provisions in the Old Port is a beloved small-plates place if you want to graze your way through dinner.

Where to Stay in Portland

For our two nights near Portland, Dad used points for a suite at the Residence Inn Portland Scarborough. Having a kitchen and a little extra space was nice since we stayed for more than one night.

Day 4: Explore Portland

Today’s the day you finally get to park the car. Instead of driving town to town, you’re settling into Portland for the whole day, lighthouses in the morning, shopping in the afternoon, and a lobster dinner on the rocks to cap it off.

Morning: Lighthouse Hopping

Start your morning at Portland Head Light, and get there early. Going first thing means you get the most photographed lighthouse in Maine almost to yourself before the charter busses roll in.

Don’t rush off after your photos, though, because Portland Head Light sits inside Fort Williams Park, a 90-acre former Army coastal-defense post that’s free to explore. You can wander the concrete gun batteries that guarded Portland Harbor through both World Wars and the ruins of the Goddard Mansion.

From there, the rest of the area’s lighthouses are a quick hop: Ram Island Ledge Light (visible offshore from the Portland Head grounds), Spring Point Ledge Light in South Portland, and Bug Light. For the full rundown on each one, where to park, where to stand for the best photo, and which are worth your time, I’ve put it all in my guide to the lighthouses around Portland.

Before you leave Fort Williams, grab a lobster roll from the Bite Into Maine food truck. I’d been looking forward to it since the night before, and it lived up to every bit of the hype.

Afternoon: Portland and Freeport

This afternoon is yours to spend in and around Portland.

Twenty minutes north of Portland, the town of Freeport is built around the L.L. Bean flagship campus, with separate buildings for apparel, hunting and fishing, a home store, and even bikes, boats, and skis. The flagship is famously open 24 hours a day and doesn’t even have locks on the doors.

This is the place to get the iconic L.L. Bean Boat and Tote, the Maine-made canvas bag that’s had a whole new life on social media lately. Pick your size and handle color and have it monogrammed right there. For a deal, cross the street to the L.L. Bean Outlet, where you’ll find overstock and seconds at 30 to 70 percent off.

If a giant outdoor outfitter isn’t really your vibe, spend your afternoon in Portland instead. After all, this is the final stop on the coastal half of the trip, so it’s your last chance to watch lobster boats coming into port and to smell that salty sea air.

Downtown is compact and easy to explore on foot. The heart of it is the Old Port, the historic district down by the harbor. You could spend an entire day exploring the cute shops, galleries, and restaurants in the area. The Eastern Promenade is large park right on the water, with harbor views that’s gorgeous in the fall.

You know how much I love an authentic travel souvenir. While cruising Commercial Street, stop in Sea Bags. Based in Maine they recycle old ship sails into bags. I’ve had one for years and it’s one of my favorite summer tote bags.

History buffs have options too: the Wadsworth-Longfellow House (the poet’s boyhood home), Victoria Mansion (an 1860 brownstone with a stunning original interior you can tour), and the Portland Museum of Art (the state’s largest, and the best rainy-afternoon pick).

And whatever you do, eat well. Portland lands on just about every “best food city” list in the country, with oyster bars, lobster rolls, and breweries within a few walkable blocks.

Evening: Two Lights Lobster Shack

Since I was shamelessly chasing the best lobster roll in Maine, we’d planned on dinner at The Highroller Lobster Co. But the night before, while Jason and I were shooting golden hour at Portland Head Light, we’d met a retired teacher and fellow photographer who told us the best lobster roll she’d ever had was at The Lobster Shack at Two Lights. That was all it took to change our plans.

As a bonus, The Lobster Shack serves whole lobster, and my sweet Daddy told us that in 85 years he’d never had one. So of course we made it happen and helped him tick that off his bucket list.

It’s exactly what the name says, a literal shack on the rocks at Two Lights, the same lighthouses we’d driven out to see our first night in Portland. The weather turned cold and rainy on us, so we couldn’t take the picnic tables out over the surf, but the dining room’s big windows kept the water in view.

I’d absolutely recommend The Lobster Shack if you can fit it in. The food is delicious, and on a clear day the views are stunning, but honestly, the moody grey skies over that surf were pretty spectacular too.

Day 5: Drive Kancamagus Highway to Stowe, Vermont

Today you trade the ocean for the mountains. The morning is one of the most beautiful drives of the whole trip, the Kancamagus Highway through the White Mountains, before you land in Stowe, Vermont for the next two nights. It’s a travel day, but you’ll want your camera ready the whole way.

Morning: Conway, NH & The Kancamagus Hwy

Today you leave the coast behind and head for the mountains. From Portland, drive to Conway, New Hampshire, where you’ll pick up the Kancamagus Highway and follow it west to Lincoln. This 34-mile route through the White Mountains is one of the most famous fall-foliage drives in the country.

One piece of advice up front, and I can’t stress it enough: leave early. It’s the same thing I preach about driving the Icefields Parkway in Banff. Both drives are stunning, and both draw serious crowds that pack the pullouts as the day goes on.

We left Portland at 7:00 and were driving the Kanc before 8:30, and even a couple of weeks before peak season, the crowds were already building. Getting there early meant we had the road and the parking lots mostly to ourselves.

Pro Tip: Parking on the Kanc
Most scenic stops require a White Mountain National Forest day-use pass. It’s $5 for the whole day and works at every stop, so you only pay once (or use your America the Beautiful pass if you have one). Cell service is spotty out here, so grab cash and download your maps before you leave Conway.

Best Stops on the Kancamagus Highway

You can drive the whole thing in about 45 minutes without stopping, but give yourself two to three hours to actually enjoy it. You don’t need to do any big hikes (we didn’t), the best of the Kanc is right off the road. Driving from Conway to Lincoln, these are the stops worth pulling over for, roughly in the order you’ll reach them:

• Lower Falls Recreation Area: Stretch your legs along the Swift River, where you’ll find swimming holes among the rocks and a picnic pavilion.
• Albany Covered Bridge: Stop for a classic photo of this covered bridge over the Swift River, framed by trees. There’s a small lot just before it, and you can walk across.
• Rocky Gorge Scenic Area: Take the short paved path to a dramatic gorge with a pedestrian bridge over the water. This was one of our favorite stops.
• Sabbaday Falls: Walk the easy 0.7-mile gravel path to a tiered waterfall. It’s the most popular stop on the route, and worth it.
• Swift River Pull-Offs: Pull over at the unmarked spots where the road hugs the river. Some of our favorite views came from these, and the water’s just a short walk from the car.

Afternoon: Lunch at Backyard, Stowe Church & Explore the Resort

We pulled into Stowe right at lunchtime and headed straight for Backyard, specifically for the duck wontons and the burgers. Neither disappointed.

Our server also pointed us to Harrisons, Piecasso, and Ranch Camp, so keep those in your back pocket if you’re in town longer.

Snap the Iconic Photos of Stowe Community Church

After lunch, go get THE photo, the Stowe Community Church steeple framed against the mountains. It’s the iconic Stowe shot, so popular the viewpoint is pinned right on Google Maps (and on the custom map I made for this post). It’s just 300 yards from Backyard, so it’s an easy stop right after you eat.

The field where you’ll line up the shot is public land used for community events, so you’re welcome to walk out and get your photo. Just park in the lower lot, the upper one belongs to the small shop and salon on site.

Check into The Lodge at Spruce Peak

After the church, head to your hotel to check in. Stowe is where Jason and I picked the hotel and broke Dad’s chain-hotel streak. We still used points, this time for a Hyatt, and stayed at The Lodge at Spruce Peak. We booked an ADA-accessible room for my dad and a junior suite for Jason and me.

Dad’s room was huge, with giant corner windows looking over the resort on one side and the mountains on the other. Our suite had a little kitchenette and a cozy sitting area with a fireplace. I loved this place enough that it’s getting its own full review, which I’ll link here once it’s up.

The resort even has its own gondola that carries guests up and over the highway to connect with the Stowe ski gondola to the top of the mountain. We’d been looking forward to the views, but the summit was socked in with fog, so we skipped it. If you ride it on a clear day, let me know what I missed.

Evening: Dinner at the Resort

We kept the evening low-key and stayed at the resort for dinner at Tipsy Trout, where the raw bar runs $2 oysters at happy hour. (Fun fact we learned from our server: Vermont law actually prohibits discounted drinks, so there are no drink specials anywhere in the state, only food ones.) It was an easy, casual end to a long day.

Day 6: Explore Stowe Vermont

Today is all about Stowe, no packing up, no long drive, just a full day to enjoy one of Vermont’s prettiest towns. You’ll browse the village shops in the morning, take a couple of scenic mountain drives in the afternoon, and finish with some of the best meals of the entire trip.

Morning: Downtown Stowe, Covered Bridges, and Apple Cider

Coffee at Black Cap Coffee & Bakery

If you’re a grab-and-go breakfast person like us, start your morning at Black Cap Coffee and Bakery, right downtown across from the Stowe Community Church. There’s almost always a line, and I promise it’s worth it. If you’d rather sit down to a full breakfast, Butler’s Pantry across the street came highly recommended by the locals we talked to.

Explore Stowe

Stowe’s adorable downtown is small, walkable, and packed with shops to explore. My favorite was Stowe Mercantile, a family-owned store with a small coffee shop and bakery inside. They carried everything from high end clothing to gifts and a whole section of Vermont-made food. If it can be maple-flavored, you’ll find it here. We picked up gifts for half our friends and family in one stop.

Stowe is compact enough to see in a morning, though it’s charming enough that you could easily spend a couple of nights here.

Historic Gold Brook Covered Bridge

Known as Emily’s Bridge, this is the only surviving 19th-century covered bridge in Stowe, but it’s actually famous for supposedly being haunted. Spoiler alert: the haunting was debunked. But, it’s a fun story that you can read about at the bridge.

Cold Hollow Cider Mill

Your next stop is the Cold Hollow Cider Mill, home of the famous apple cider donuts. This is such a fun stop. There’s a large gift shop with souvenir type items and you can buy hot or cold cider. The on-site restaurant has fantastic reviews if you are ready for lunch.

Follow the apples on the floor to the cider pressing room at the back where you can watch them turn whole apples into their delicious cider. If you don’t want a whole cup, you can get a small free sample back there.

Explore Waterbury

Our plan was to explore Waterbury and grab lunch in town. But once again, shoulder season caught up with us, most of the restaurants weren’t open for lunch, so we didn’t stay long. By that point we’d eaten nothing but carbs (delicious carbs, but still), and we needed a real meal, so we headed back to Stowe.

Plan better than we did, and Waterbury is worth a stop. Pop in and out of the shops, then visit the Cabot Creamery store or take a tour of the Ben & Jerry’s factory. The whole town looks like a postcard.

Afternoon: Lunch and Scenic Drives

Looking back, I’m so glad the Waterbury restaurants were closed, because it sent us back to Stowe and to Idletyme Brewery. It was one of the best meals of our whole trip. We split the dry-rub wings and the French onion soup. Dad loved his fish and chips, and Jason raved about the herb-grilled chicken sandwich. And my wedge salad was out of this world.

After lunch, head north to Smugglers Notch, a mountain pass of tight hairpin turns climbing through the mountains. The road gets so narrow in spots that RVs and large trucks can’t make it through. (There’s a little “obstacle course” of barriers right before the entrance, if you can fit through those, you’ll fit through the Notch.)

We almost skipped this drive because it was raining, but the owner of Stowe Mercantile told us the Notch is even prettier in the rain. She was right, it was stunning. (She also mentioned she did her driver’s ed on that road at fifteen, which tells you something about how locals grow up here.)

Another option is the Stowe Mountain Toll Road up to the top of Mount Mansfield. We skipped it because the summit was socked in with fog, but on a clear day it’s a great way to take in the views. It’s a 4.5-mile drive, credit card only, and there’s a per-vehicle fee plus a charge for each additional passenger.

From there, make your way to the Von Trapp Family Lodge. Yes, that Von Trapp family, from The Sound of Music. After escaping Austria, they settled in Vermont because it reminded them of home, and they still own the resort today, all 2,600 acres of it, open year-round.

The rain cut our visit short, so we only did a quick run-through, but I’d love to come back and stay a couple of nights. If you’re a fan of the movie, it’s a fun stop.

Evening: Stowe Recreation Path + Dinner

If you’ve got some daylight left and the weather’s cooperating, the Stowe Recreation Path is a lovely way to wind down. It’s a paved, mostly flat 5.5-mile greenway that starts behind the Stowe Community Church and follows the West Branch river through meadows and woods, with mountain views the whole way. Walk or bike as much or as little of it as you like.

For dinner, do what we did and ask around, because every local we talked to pointed us to Piecasso. (And really, has there ever been a better name for a gourmet pizza shop?) They. Were. Not. Wrong. It’s a funky local spot serving some of the best pizza we’ve ever had.

Jason got the Carcass and loved it, and I got the fresh mussels in garlic cream sauce. Don’t let the name fool you, this is a full kitchen, with braised short ribs on the menu and a whole lineup of vegetarian pizzas. I could eat here every day.

Day 7: Covered Bridges, Woodstock & Drive to Boston

Morning:Covered Bridges of Vermont

On our last full day, we started back at Black Cap Coffee and Bakery before hitting the road.

The plan: see several covered bridges, have lunch in Woodstock, and end the day in Boston for our flight home. And it sort of happened that way.

Vermont Covered Bridges

Even with the detour, we made it to every bridge on our list (all marked on the map).

• Middle Bridge: Right at the edge of Woodstock village. It looks centuries old, but it was built in 1969 the traditional way, with wooden pegs instead of nails, and dragged into place by a team of oxen.
• Taftsville Covered Bridge: The bright red one east of town, built in 1836 and one of the oldest in the country. It has survived floods that washed away three earlier bridges on the same spot, plus a direct hit from Hurricane Irene.
• Cornish-Windsor Covered Bridge: The showstopper. At about 450 feet, it’s the longest wooden covered bridge in the country, and you drive right across it from Vermont into New Hampshire.
• Quechee Covered Bridge: Worth the stop for what sits right at the foot of it, Simon Pearce, a high-end glassblowing studio in a restored mill over the falls. You can watch artisans blow glass, browse the gallery, or have lunch overlooking the water. (If you’ve got a soft spot for Jake from Sweet Home Alabama, this one’s for you.)

Afternoon: Woodstock Vermont

I didn’t think I could love a New England town more than Stowe, until we pulled into Woodstock. Stowe is a lovely ski town, but Woodstock is the classic New England village, with serious Gilmore Girls vibes. From the historic green to the old homes, the quaint shops, and the creek running through downtown, I was instantly smitten.

Plan to spend a couple of hours here, though you could easily spend the whole day (and a lot of cash) just in the shops. Thanks to our wrong-turn fiasco, we didn’t have nearly enough time. We did manage a little shopping, and I had to have a maple creemee from Woodstock Scoops, the soft-serve this area is known for.

That was all we had time for, but if you didn’t lose two hours to a wrong turn, two stops just outside town are worth your time. Pick one:

• Billings Farm & Museum: a working Jersey dairy farm where you can meet the cows, watch cheese-making, and tour a restored 1890s farmhouse.
• Sugarbush Farm: a family farm five miles out a winding back road, where you can sample fifteen kinds of cheese and four grades of Vermont maple syrup and see how the trees are tapped.

We wanted to reach our Boston hotel before dark, so we skipped lunch, set the GPS (with the correct address this time), and left Woodstock behind.

Evening: Last Night in Boston

For our last night we stayed at the Residence Inn Boston Logan Airport in Chelsea. With an early flight out, you want to be close to the airport, and this put us ten minutes from the terminal.

We pulled in tired and hungry, but full of memories from an unforgettable New England fall road trip. I wanted one last lobster roll before heading home, so we ordered takeout from Legal Sea Foods and spent the evening going through our photos from the week.

What to Pack for a Fall New England Road Trip

If you take one thing from this section, let it be layers. New England fall weather swings all over the place: daytime highs sit in the upper 50s to mid 60s, but nights get nippy, dropping into the 40s on the coast and the 30s up in the mountains, sometimes all in the same day.

The trick isn’t packing heavy, it’s packing pieces you can add and peel off as you go. A good jacket isn’t optional, and neither is a packable rain layer, you’ll hit at least one wet day, and the mountains can surprise you.

Here’s the clothing rundown:

• A warm jacket and a packable rain jacket
• Jeans (my go-to for the whole trip) and a few long-sleeve tops
• A cozy sweater or two for layering
• A hat and light gloves for cold mornings, especially in the mountains
• Comfortable, broken-in walking shoes
• Something a little nicer for dinner, a few of these towns have lovely restaurants

I’ve pulled together everything I packed, with links, in my New England fall packing list .

The practical road-trip kit. This is the part most packing lists skip, and it’s the stuff that actually made our days easier:

• Cash. Several parking lots on this route are cash-only, including a few of the scenic-area and lighthouse lots, and the Kancamagus pass stations. Keep small bills in the car.
• A portable charger. Between navigating, photographing, and checking foliage maps, your phone will drain fast. A power bank saves you.
• Offline maps. Cell service disappears in the White Mountains and parts of rural Vermont, so download your route before you head into the mountains.
• A reusable bag or small cooler. You will buy maple syrup, cheese, cider, and probably a flannel. Give yourself room to get it home.
• A refillable water bottle and snacks for the long stretches between stops.
• Sunglasses. The fall sun is low and bright, and it bounces right off the water and the leaves.
• Your camera and extra batteries. Fall here is a photographer’s dream, and the cold drains batteries fast. My full setup is in my camera gear list on Amazon.

One more, if you’re traveling with someone who has mobility needs: bring the disability placard. New Hampshire, Maine, and Vermont all offer free metered parking with one.

FAQs About Planning a New England Fall Road Trip

Start Planning Your New England Fall Road Trip

This trip turned out to be one of our all-time favorites, seven days of lighthouses, lobster rolls, mountain drives, and small towns that each somehow felt like the most charming one yet.

If there’s one thing I’d do differently, it’s give it more time. We packed a lot into a week, and we loved every minute, but I’d stretch it to ten days next time so there’s room to slow down and actually linger in the places we rushed through.

However many days you have, the most important thing is to just go. The foliage, the food, the coast, the mountains, it all lives up to the hype, and then some.

If you’re ready to start planning, here are a few of my other posts to help you dig deeper:

• Things to Do in Rockport, Massachusetts
• Where to Stay in Rockport, Massachusetts