The Perfect 7 Day New England Fall Road Trip

How to plan a fall road trip in New England

There are a few different ways you can go about planning a road trip in New England. The most important piece of advice is to start planning early. This is an incredibly busy season and many leaf peepers book their accommodations months in advance. Ideally, I suggest you should start looking at hotels in late July or early August. By August your hotels and activities should be booked.

Whether you’re flying to the northeast or driving from a nearby state, the Boston, Massachusetts area is a great jumping off point. Boston is right in the middle of New England and Massachusetts boarders four other New England states. If you have to fly, Boston Logan is a major international airport and an easy destination to fly into to start the road trip.

With Boston as your home base, there are a few different ways you can go. While a one week road trip is enough time to see New England’s fall highlights, you will still have to prioritize certain places over others. This itinerary outlines what I think are the best places to see during fall in New England. In my opinion, the absolutely best states to visit during the fall are Vermont, New Hampshire and Massachusetts.

This one week New England fall road trip focuses on staying for multiple nights in one hotel used as a home base. Rather than switching hotels every night, I like to find one hotel that’s in the middle of a lot of sights. You’ll stay at the first hotel for 2 nights (you can cut this down to 1 night if you prefer your week trip is 6 nights away), the second hotel for 2 nights and 3 nights at the last hotel.

The ultimate question: A planned fall road trip or a more flexible itinerary?

Cider donuts and apple cider

Now that you know the states you’ll be covering on your New England road trip, you need to decide if you’re going to meticulously plan out every detail or if you prefer to wing it a bit. There are pros and cons to each approach.

Meticulously planning out every detail of your fall road trip allows you to know exactly where you will be on each day. You’ll have your hotels, dining reservations and activities booked and won’t have to second guess anything. A con to this approach is the lack of room for spontaneity. You’ll quickly find that New England is full of interesting roadside attractions and charming towns, and sometimes you stumble upon the best places unexpectedly. If you’re too tightly scheduled you may miss the cute farm stand lined with pumpkins that you drive by. Or a country shop with a sign claiming they have “the best apple cider donuts.” And that would be a shame.

Another con to planning out every detail of your trip is that fall foliage timing can be hard to nail down. Peak foliage dates can change quickly based on weather. One town (based on its elevation and rain levels) can be experiencing peak foliage, while a short drive away another town is all green. We can do our best guessing when peak foliage will be, but it’s not always exact.

Going with the flow and not planning out every day of your fall New England road trip allows you to change your plans to accommodate the latest foliage reports. You can also take your time going off the beaten path and exploring towns and fall farms you stumble upon.

A con to this approach is that New England in the fall season is incredibly busy. Hotels, restaurants and ticketed activities book up months in advance. If you don’t have reservations you may miss out on things you want to do.

My recommendation is to plan out your hotels and must-do dining and activities, and leave a little wiggle room for exploration and following the foliage. Use this itinerary as your guide to the region’s best and most impressive fall sights, hotels and activities, and determine what is not-miss to you and where you can be flexible. This is a great resource to keep updated on the latest foliage reports.

When is the best time to take a fall road trip in New England

I mentioned above that it’s hard to determine when fall foliage will be peak in New England. The exact dates change every year and it’s impossible to nail down specifics.

The foliage conditions change from year to year based on the weather. On a warmer year the leaves could turn later, on a colder year they could go earlier. One bad rainstorm could also impact the foliage colors. Given that, it’s pretty safe to assume that the destinations further north and at a higher altitude will turn to peak foliage sooner than the more southern and coastal destinations.

While it’s hard to determine when the true peak foliage will be, it typically takes place in the same general timeframe – early through mid-October. I recommend planning your fall visit to New England during this time period. Even if you miss the peak foliage, you will still see some beautiful fall colors throughout the various towns and states I recommend in this fall road trip itinerary.

For the 2026 fall season, experts are anticipating the foliage to hit peak colors on a typical or slightly later schedule. This means the most vivid colors will show in late September in the more northern and elevated destinations and early through mid-October for the more southern towns. This information is as of August 1, 2026.

A favorite fall outfit in Woodstock, Vermont

What to pack for a fall road trip in New England

The best piece of packing advice for any type of fall travel in New England is to bring layers. The weather can change rapidly during the autumn and while it may feel warm during the day, it gets cool at night.

This road trip itinerary also takes you through mountain regions and on hikes where the temperatures will be cooler. Rain and wind are also common during the fall in New England. A good rain jacket and shoes are a must! You should also be prepared for muddy conditions if you’re walking in the country or at a farm.

When I’m visiting New England in autumn I like to look put together but appropriate for being in nature. My go-to jacket is this classic style that I wear all fall long (it’s also great in the spring). If you’re looking for something a little more affordable, this is a great fall jacket that’s under $50, and I also love this style that’s a little bit longer and is also under $50.

For waterproof shoes that still look cute I opt for these that look more refined than typical rain boots. They’re waterproof and very comfortable to walk in and trek through fields and farms.  They also don’t look out of place with jeans and a sweater. If you’re looking for a classic rain boot, this pair is hard to beat thanks to its affordable price, range of colors and modern mid-calf height.

For exploring New England’s charming towns, I like to dress up a bit more. My go-to fall outfit on a sunny day is usually a cozy sweater with a skirt and knee-high boots with a low or kitten heel. It feels polished without sacrificing comfort, and it’s perfect for wandering through downtowns, browsing boutiques, stopping for coffee, or heading out to dinner. Here are the boots shown in this photo. I love wearing them in the fall with dresses and skirts and own them in brown and black suede. And this is a great fall leaf printed sweater that’s perfect to pair with a denim skirt or jeans. It looks similar to styles that sell for close to $150 and this version is under $30.

First stop: Salem, Massachusetts (2 nights)

A note about visiting Salem in October: Please note that Salem is incredibly packed with tourists each October. And October 2026 marks Salem’s 400th anniversary, so the town is expected to be even more busy than usual this year. If there are certain things you want to do, it’s imperative to make reservations early and have your plans set as early as possible. Some people say the high October crowds make it miserable, but I disagree. With the right planning, and going into the trip knowing it’s going to be busy, you’ll have a great time. October is a time when the town comes alive and there are special seasonal activities and events happening all around Salem; it has a special vibe that you can’t recreate in other months. 

The first stop on your 7 day New England fall road trip is Salem, Massachusetts for two nights. Salem is one of my favorite places to visit in the fall. It’s a historic port city that’s close to Boston, and it really comes alive during autumn.

I visit Salem every year (check out my comprehensive travel guide to Salem, Massachusetts and my Instagram Reel travel guide to Salem here) and think it’s a great place to kick off your fall road trip because it’s incredibly festive in October. The town is most well known for The Salem Witch Trials that occurred in the 1690’s. The city does a great job at teaching the history of those unfortunate events and remembering the victims, while also leaning into the spooky fun that the Salem conjures up. While this part of the road trip doesn’t focus on foliage, it will really get you in the fall spirit and start your trip on a fun, high note.

Salem is 16 miles from Boston. I recommend starting your drive from Boston in the morning and getting to Salem before noon.

The best things to do in Salem, Massachusetts

When you arrive, fuel up for your day of sightseeing with brunch at Gulu-Gulu which is a bohemian cafe right in the center of town. I love the breakfast options here (served all day) and they have great speciality lattes! I always order their Nutty Professor which is a latte with chocolate and toffee nut syrup.

Salem Pioneer Village

If you stop at Gulu-Gulu first you’ll be well situated in the center of Salem’s action. Right in front of Gulu-Gulu is one of Salem’s famous landmarks, the Bewitched Sculpture. This depicts actress Elizabeth Montgomery riding a broomstick and it’s located at the end of one of the best places to walk around in Salem, the Essex Street Pedestrian Mall. That’s where I recommend heading next.

Exploring Essex Street

Essex Street, Salem’s pedestrian-only main thoroughfare, is lined with restaurants, boutiques, museums, and historic attractions, making it the heart of the city’s activity year-round. In October, it transforms into the vibrant center of Salem’s annual Haunted Happenings festival, a month-long celebration featuring parades, street performers, pop-up markets, live entertainment, and special events. Beyond the official festivities, Essex Street comes alive with costumed performers, witches, and entertainers who embrace the Halloween spirit, creating an energetic, immersive atmosphere.

Essex Street is also where you will find the Peabody Essex Museum, a world renowned art museum. The museum has an ongoing exhibition covering The Salem Witch Trials of 1692.

I recommend you spend a few hours strolling along Essex Street, checking out the Peabody Essex Museum and going into shops.  If you’re in the mood for an activity, you’ll also find haunted houses and walk-through attractions on Essex Street. My friends and I had a fun time going through the International Monster Museum and the World of Wizardry.

Aura reading at HausWitch

Shopping in Salem

Some of the best shops on Essex Street in Salem include Crow Haven Corner, dubbed the oldest witch shop in Salem, Wynotts Wands a magical wand shop with Harry Potter vibes, and Ascend a boutique that has great witchy gifts and crystals. I’ve also gotten a tarot card reading at Ascend and it was a fun experience. You can schedule this in advance, or walk in and see their daily availability.

I’m a huge shopper, so browsing Salem’s boutiques is one of my favorite things to do. While you’ll find plenty of fun witchy souvenirs throughout the city, I personally love the more elevated, aesthetic, and fashion-forward shops. The best part is that there’s truly something for everyone.

Just off of Essex Street you’ll find four of my favorite boutiques in Salem, HausWitch, Oak and Moss, Nocturne and Blackcraft. HausWitch is located on Washington Street and it’s a great store to learn about and purchase crystals, candles, tarot decks, and other cute witchy home decor items. HausWitch also offers aura readings which I’ve done twice and is always a fun experience! After having your aura photo taken, you’ll sit down with an expert who walks you through your reading and explains what the different colors and energies in your aura represent. Oak and Moss is right across the street from HausWitch and they sell beautiful non-witchy home goods, accessories, and gifts as well as plants and plant accessories.

Blackcraft is a massive store that has a few different section. There’s the main shop that has an incredible selection of clothing, accessories, and home goods that all lean into the witchy gothic aesthetic. The team does a great job of merchandising the store and there are different sections featuring different themes and items. In the back of the store is Blackcraft Coffee, which I consider to be Salem’s best coffee shop (more on this below), and there’s also a haunted house, Haunt Blackcraft, that’s truly one of the most beautiful and aesthetic haunted houses I’ve ever walked through. Blackcraft is also home to Salem’s largest witch, which hangs from the ceiling in the middle of the store!

Nocturne boutique in Salem

Nocturne is located around the block on Front Street. It’s a gothic boutique and hands down my favorite shop in Salem, I never skip it when I’m in town. The entire store is beautifully curated, with a moody, elevated aesthetic and a great mix of home decor, candles, gifts, clothing, and accessories. One of the coolest things is that they completely change the boutique’s theme and decorations every year, so there’s always something new to see. In the back, they also have a bookstore that’s packed with gothic, spooky, fantasy, and romance books. I could spend forever browsing the shelves, and I always end up leaving with at least one new book.

Historical Sights in Salem

One of my favorite things about Salem is that history is everywhere. If you continue down Essex Street past the Hawthorne Hotel toward the waterfront, you’ll reach the House of the Seven Gables, one of Salem’s most iconic historic homes and the inspiration for Nathaniel Hawthorne’s famous novel. You can tour the preserved 17th-century mansion, its gardens, and the grounds overlooking Salem Harbor.

At the opposite end of town, just a few blocks from Essex Street, is “The Witch House” aka The Jonathan Corwin House, the only remaining structure in Salem with direct ties to the 1692 Salem Witch Trials. It was once the home to Witch Trials Judge Jonathan Corwin. Now the house is a museum which you can tour and learn more about life and the events surrounding the witch trials. This is another attraction that’s worth reserving ahead of time during the busy fall season. The outside of the house is one of the most famous photo spots in Salem. You can’t leave without getting your photo taken here, but keep in mind that if you’re visiting in October it’s going to be incredibly crowded with tourists lining up to get the perfect shot. If you’re dead set on getting a great picture here I recommend getting up early.

Another not-miss historical sight is the Old Burying Point Cemetery, located near the Salem Witch Trials Memorial, just off of Essex Street. Dating back to 1637, it is one of the oldest cemeteries in the United States and the final resting place of several notable Salem figures, including Judge John Hathorne, one of the judges involved in the Salem Witch Trials.

Hocus Pocus Filming Locations in Salem

Of course no trip to Salem is complete without visiting a few filming locations from Hocus Pocus. Much like the town’s historical sights, the filming locations are also scattered throughout Salem and you’ll be passing them as you shop and explore around town.

One of the most recognizable locations is the Ropes Mansion, which served as Allison’s house in the film. It’s located a few houses down from The Witch House. The mansion is a beautiful historic home with gardens that are open to the public. Fun fact: the Ropes Mansion is considered one of Salem’s most haunted spots!

Salem Town Hall

In the heart of downtown, you can also visit Salem Old Town Hall, which was featured as the site of the Halloween party scene where the Sanderson Sisters perform “I Put a Spell on You.” The building is located right in the historic district, making it an easy stop while exploring Essex Street and the surrounding area.

Another fun stop is Pioneer Village, which appears in the opening scenes of the movie as the 17th-century village setting. The village is a living history museum where you can step back in time and explore replica colonial buildings, gardens, and historic demonstrations. Occasionally Pioneer Village will have special events, so check the website and calendar. Just keep in mind that Pioneer Village has limited and sometimes unusual hours, so check the schedule before visiting.

Another filming location will bring you slightly outside the main downtown walking area, to Ocean Avenue. This is where you’ll see the exterior of Max and Dani’s house, located in a residential neighborhood near Salem’s waterfront. While the house is privately owned and only visible from the outside, it’s a fun photo stop for any Hocus Pocus fan, just keep in mind it’s private property and please be respectful.

Salem walking tours

I’m usually not a big walking tour person and prefer exploring a town at my own pace, but Salem is one place where I actually love taking a tour. The guides are incredibly knowledgeable and bring the city’s history to life with fascinating stories, ghost tales, and fun facts as you walk through Salem’s most iconic sights.

You can absolutely visit Salem’s historic landmarks and Hocus Pocus filming locations that I mentioned above on your own, but a walking tour is a great way to learn the stories behind the places you’re seeing. Plus, Salem is an extremely walkable city, making it easy to fit a tour into your itinerary while still covering a lot of ground.

While walking tours are offered throughout the day, I personally love taking one in the evening or after dark. The spooky atmosphere makes the ghost stories and legends even more fun, and its a good after dinner activity. There are many different types of tours to choose from, including tours focused on the Salem Witch Trials, spooky ghost walks, and even Hocus Pocus themed tours. Some of my favorite Salem tour operators are Witch City Walking Tours, Spellbound Tours and Black Cat Tours. I always opt for a tour that leans more on the spooky and ghost story side, as that’s the Halloween vibe I like when I visit Salem!

Hotel recommendations in Salem, Massachusetts

Salem has some fantastic boutique hotel options, especially if you love staying somewhere with history and character. The beautifully appointed Merchant Hotel is a great example, combining historic charm with a stylish, modern feel. The hotel is also said to be haunted, adding to Salem’s spooky appeal. Fun fact: George Washington stayed here during a visit to Salem, and the property even has a suite named the “George Washington Suite.” Located right near HausWitch and within walking distance of many of Salem’s top attractions, it’s a great home base for exploring the city.

My favorite hotel to recommend for a Salem visit is the Hawthorne Hotel. This historic property sits at one end of Essex Street, putting you right in the middle of the action and within easy walking distance of many of Salem’s best restaurants, shops, and attractions. The hotel is named after famed Salem-born author Nathaniel Hawthorne and first opened in 1925. It’s a member of Historic Hotels of America and remains one of the city’s most iconic places to stay. I also love that the Hawthorne Hotel is dog-friendly. And, fitting for Salem, the hotel is rumored to be haunted.

Other hotels that I like in Salem include The Coach House which is a luxury boutique inn that’s in a renovated 1879 Victorian Mansion. It’s in a quiet residential area and is a nice place to escape the hectic Salem energy at the end of each day. The Hotel Salem is owned by the same company that owns The Merchant. It’s a larger hotel right on Essex street and it has a popular rooftop restaurant and bar. It has a more energetic atmosphere than The Merchant, if that’s what you’re looking for.

Blackcraft coffee in Salem

The best food and drinks in Salem, Massachusetts

The food scene in Salem is surprisingly great, and just like with hotels and activities, I recommend making reservations in advance during the fall season.

For a casual afternoon stop, head to Notch Brewery for craft beers and light bites. Located along the South River, Notch has both a taproom and a beer garden, and it’s a great place to relax during a long day of exploring.

For dinner, Bambolina is one of my favorite recommendations. Their menu focuses on handmade pizza and creative dishes, making it a great spot for a casual but delicious meal after a day of sightseeing.

For a more elevated dining experience, Settler is a great choice for a special night out. In years past, they’ve offered a seasonal tasting menu in October that’s definitely on the pricier side, but it’s a memorable experience if you’re looking to splurge. The menu changes seasonally and focuses on thoughtful, creative dishes. For a taste of classic New England seafood, Turner’s Seafood is a must. It’s a great spot for clam chowder and fresh oysters, and I especially recommend stopping in if you’re craving a seafood-focused meal while in Salem.

If you’re looking for a fun nightcap afterward, stop by Rockafella’s, a casual restaurant and bar with a spooky history… be sure to ask your server about the “Lady in Blue,” one of Salem’s many ghost stories. Another fun option is Flying Saucer Pizza Company, which has a long list of spooky-themed cocktails that fit perfectly with the Halloween atmosphere.

For dessert, don’t miss Goodnight Fatty for incredible homemade cookies. They’re the perfect late-night treat after a full day of walking around Salem.

One of my favorite October food stops in Salem is Blackcraft Coffee, the coffee shop located inside the Blackcraft store. The coffee shop is in the back of the store; it’s small and beautifully decorated. There’s no seating, and you’ll simply order your drink to go, but if you’re visiting Salem from mid-September through mid-November, they require online reservations to simply go in and order your take out drink. Reservations go fast, so keep an eye on their website and grab a time slot while you can. Trust me, it’s worth it. Their pumpkin spice latte is one of the best I’ve ever had.

Second stop: Bretton Woods, New Hampshire (2 nights)

After kicking off your New England road trip in Salem and celebrating spooky season in the way that only The Witch City can, it’s time to head north into nature. The second destination on your 7 day New England fall road trip is the mountain town of Bretton Woods, New Hampshire. The drive from Salem to Bretton Woods, New Hampshire is 160 miles and the longest drive on your itinerary, but should still clock in at under 3 hours.

Drive right to your accommodation for the next two nights, The Omni Mount Washington Resort. This historic hotel is located in New Hampshire’s White Mountains. It’s a great home base to explore the state’s fall foliage and puts you in close proximity to some of the region’s best fall hikes.

Hotel recommendation for fall in New Hampshire- The Omni Mount Washington

The back porch at Omni Mt Washington

The Omni Mount Washington Resort was built in 1902 by New Hampshire native Joseph Stickley who made his money in coal mining and the Pennsylvania Rail Road. The hotel is a massive Spanish Renaissance-style building with 269 guest rooms and suites. The resort recently underwent a major renovation that included the construction of a gorgeous Presidential Wing. I recommend booking a room early so you can reserve your ideal dates, and booking it in this wing. I stayed in a Presidential Wing room in October 2023 and really enjoyed the accommodation.

The star of the show at The Omni is the resort’s backyard. This is a sprawling lawn with fire pits, Adirondack chairs and a massive porch that overlooks that mountains.

If you didn’t get enough spookiness in Salem, you’re in luck because The Omni Mount Washington is also a haunted hotel. Multiple ghost hunting shows have filmed here. The lore is that Joseph’s wife, Carolyn, haunts the property. It’s said that guest room 314 is the most haunted place at the resort.

Two nights is a sufficient amount of time to use The Omni Mount Washington Resort as your home base to explore. This is a very rural area and most of the activities are foliage-focused. You’ll set out on short drives from the resort to various mountains and parks. Since these activities are weather dependent, you can do them in any order that makes sense when you’re there.

The best fall activities in New Hampshire

Fall in New Hampshire is all about the mountains, crisp autumn air, and what some consider to be the most beautiful foliage in New England. The White Mountains truly come alive in the fall.

Best fall hikes in New Hampshire

Artist Bluff View

A very popular fall hike in the area is Artists Bluff. The trailhead is about 18 miles from The Omni. It is one of the best fall hikes for its beautiful payoff with a relatively easy climb. It’s a short hike that leads to breathtaking views of the New Hampshire foliage. The trail is a 1.5 mile loop, or if you’d like to get to the top quicker, there is a shortcut that is a moderately steep .5 trail right to the top. Most people of all ages and in relatively decent shape can do this hike. At the top you will be rewarded with views of Echo Lake and the White Mountains.

Flume Gorge is 23 miles from the hotel. It’s a natural gorge that extends 800 feet at the base of Mount Liberty. The flume trail is a 2 mile loop that takes about 1.5 hours. It’s a beautiful park and you’ll see waterfalls, covered bridges and reflection pools. There are a lot of stairs and a boardwalk that will take you through the gorge. Flume Gorge is located in a New Hampshire state park and there is an entry fee.  As of August 2026, online ticket prices are $18 for adults and $16 for children 6-12, children under 5 are free. Visitors can purchase tickets online or at the park, and there is a savings of $3 when the reservations are made ahead online. Certain peak times can sell out, so I recommend reserving your tickets online.

Best fall views in New Hampshire without a hike

Bretton Woods gondola

Conway Scenic Rail is a heritage old fashioned rail excursion about 30 miles from the resort. The train meanders through the Mount Washington Valley and Crawford Notch and it’s a great way to see fall foliage from a unique perspective, and without a hike. The Conway Scenic Rail offers a variety of trips. I did the Conway Valley Train experience which lasts around 55 minutes. This train ride departs from and returns to the Victorian North Conway train station that was built in 1874. Purchase tickets ahead of time as time slots do sell out in the fall.

Located right by The Omni is Bretton Woods Ski Gondola, a scenic gondola ride. It’s a free experience for Omni lodging guests. A 12-minute gondola journey offers panoramic views of Mount Washington and The Presidential Range in the White Mountains. At the top of the gondola, visitors can find a variety of food and drink options or hike around the mountains.

There’s a lot to see in New Hampshire, but make sure to also carve out time to enjoy the resort. Before or after you set out to explore each day, spend time on the grounds and back porch. The property is 1,900 acres and surrounded by 800,000 acres of national forest.

The resort has so much to enjoy, with a 25,000 square foot luxury spa, outdoor heated pools, hiking trails, an 18-hole and 9-hole championship golf courses, stables and equestrian activities such as trail rides and carriage rides. My favorite thing to do at the property was sit on the big back deck and admire the colorful leaves dotting the mountains.

Restaurant recommendations in Bretton Woods, New Hampshire

As mentioned, this is a pretty remote area. There aren’t a lot of restaurants to choose from and I ate most meals on the resort property. The resort’s 1902 Main Dining Room has a delicious breakfast buffet and Stickney’s Restaurant is a casual steakhouse and pub that’s perfect for dinner.

Foliage in New Hampshire

We also had a delicious dinner at Fabyan’s Station which is a restaurant in a restored train station. They serve a casual menu that focuses on burgers and BBQ items. Fabyan’s Station is part of The Omni but located a short drive away and the resort’s shuttle can drop off and pick up.

If you’re a coffee lover and looking for a cafe off the resort property, I absolutely love Autumn Nomad. This coffee shop is located 27 miles from the resort and is one of the cutest coffee shops I’ve ever visited. I love their speciality coffee drinks and ordered an amazing pumpkin latte. I also had a grilled vegetable sandwich that was delicious. While this cafe isn’t very close by, it is in the direction of the Conway Scenic Rail and you could stop for a pick-me-up before or after your train ride.

Autumn Nomad is located in the charming small town of Jackson, a picturesque village known for its covered bridges, distant mountain views, and annual Pumpkin People display each fall. While I personally love the grand, iconic experience of staying at The Omni Mount Washington Resort, Jackson is a wonderful option if you’re looking for a quieter, more intimate small-town atmosphere. I stayed at the Inn at Thorn Hill on a winter trip to New Hampshire and really enjoyed its charming, cozy atmosphere and welcoming staff.

Third stop: Woodstock, Vermont (3 nights)

Kanc Highway

One of the best ways to experience fall in New England is to turn your hotel transfer into a scenic adventure. As you continue your trip from New Hampshire to your next destination of Woodstock, Vermont, consider taking a detour through the famous Kancamagus Highway, one of the most beautiful fall foliage drives in the country.

The 34-mile scenic byway winds through New Hampshire’s White Mountains and is known for its incredible autumn colors, mountain views, waterfalls, and scenic overlooks. Plan extra time to stop along the way. Some of the best viewpoints to pull over include Sabbaday Falls, Rocky Gorge Scenic Area, and the many roadside overlooks where you can take in the foliage. You can purchase a self-guided audio tour of the Kanc which will tell you about the best stops and pull overs along the route.

The drive is especially spectacular in peak fall, when the mountains are covered in vibrant shades of red, orange, and gold. After exploring the Kancamagus Highway, continue west into Vermont for the next stop on your New England fall road trip: the charming town of Woodstock, where you’ll find covered bridges, historic buildings, and classic autumn scenery. Please note that taking the Kancamagus Highway on your way to Woodstock is not the most direct route. You can bypass this if you are tight for time, but I do recommend trying to fit it in. 

Woodstock, Vermont is my favorite place in New England to visit during the fall. It’s a charming and idyllic town that truly comes alive in autumn. Check out my full comprehensive travel guide to Woodstock, Vermont and here is my Instagram travel guide to Woodstock.

The drive from Bretton Woods to Woodstock is 90 miles if you go direct and skip the Kanc. Once in Woodstock, check into your hotel for the next three nights, The Woodstock Inn and Resort. This is one of my favorite hotels in the world and you can read my detailed thoughts on staying at the hotel here – Review of The Woodstock Inn and Resort in Woodstock, Vermont.

Middle Covered Bridge in Woodstock, Vermont

The best things to do in fall in Woodstock, Vermont

Check into the resort and leave your bags and set off to explore downtown Woodstock. One of the main reasons I love The Woodstock Inn and Resort is that it’s located right in the center of downtown Woodstock. It’s incredibly walkable to some of the area’s best dining, shops and sights. In fact, right across from the resort is one of the landmarks of Woodstock, the Middle Covered Bridge.

Shop around downtown Woodstock, Vermont

Spend the afternoon going in the shops along the two main roads that run through Woodstock, Central Street and Elm Street. There’s so much to see, including Vermont’s longest running independent bookshop, The Yankee Bookshop. I also love the boutiques around town. Vermont Flannel is an iconic Vermont store with cozy, handmade flannel shirts and other products in a variety of colors. 37 Central Clothiers is my favorite clothing boutique and Woody’s Mercantile is a great shop for fall home goods and gifts. F.H. Gillingham and Sons is a general store that has been in business for over 130 years. They sell gift items and groceries.

Maple syrup farms and fall hikes near Woodstock, Vermont

The hiking around Woodstock is great because the town is located in The Green Mountains. A fall foliage hike at The Pogue and Mount Tom trail is a great way to start a day in Woodstock. This hike is moderately difficult and takes around two hours to complete.

You can also check out a local cheese and maple syrup farm, Sugarbush. This farm is situated in the mountains on 500 acres and the views are spectacular. You can visit the cheese work room, walk the maple trail and buy Sugarbush products at the gift shop.

There are also many breweries in the area that you can visit. Some of the best breweries are Long Trail, Harpoon and River Roost.

Au Comptoir in Woodstock, Vermont

Dining in Woodstock, Vermont

Grabbing cocktails from the bar at The Woodstock Inn’s main restaurant, Red Rooster, and taking them outside to enjoy in the Adirondack chairs on the resort’s beautiful front lawn is one of my favorite ways to start an evening in Woodstock. If you’re looking for a cocktail outside of The Woodstock Inn, Au Compoir is an incredibly chic cocktail bar located just a few minutes walk from the resort. This modern craft cocktail bar serves delicious drinks and small plates. I always like checking out their seasonal cocktail list and last fall I had one of the best drinks I’ve ever had, a riff on a pumpkin espresso martini.

Some of my favorite restaurants in town include Melaza Bistro, a restaurant that focuses on Caribbean tapas and entrees. I love their vegetarian paella! As of August 2026, it says the restaurant is temporarily closed. It’s my hope that it will open for the fall season. Other restaurants that I love in Woodstock include the casual Worthy Kitchen that’s popular for its burger and local Vermont beers (located right outside the downtown) and Santé, a farm to table bistro.

For lunch or breakfast, you can’t miss the popular Mon Vert cafe and coffee shop, which has typical breakfast and lunch sandwiches and seasonal lattes. Another great coffee option in Woodstock is Abracadabra, which focuses on expertly brewed coffee.

If you’re looking for a sweet treat, grab a Vermont delicacy, the Maple Creemee ice cream, from Woodstock Scoops.

Day trip from Woodstock to Stowe, Vermont

On one of your days in Vermont, I recommend grabbing a quick breakfast at Mon Vert and driving an hour north to Stowe. Stowe is another charming Vermont town that’s full of adorable shops and restaurants, and it’s worth a visit.

I like walking around Stowe’s main shopping street, Main Street. You can also tour the nearby Ben & Jerry’s Factory and check out Cold Hollow Cider Mill. If you’re in the mood to be more active, there is great hiking in nearby Smuggler’s Notch State Park.

Dog lovers can’t miss one of the area’s best activities, The Golden Retriever Experience at Golden Dog Farm. Golden Dog is located about 30 minutes north of Stowe and it’s a gorgeous farm that has apple trees and produces honey and maple syrup.

Cold Hollow Cider Mill

The farm is home to a group of Golden Retrievers (hence the name) and they offer an experience where visitors can spend an hour playing and hanging out with their adorable Golden Retrievers. Guests can also sample the farm’s products and every person gets a photoshoot with the gang of Goldens. Here’s my review of the The Golden Retriever Experience at Golden Dog Farm.

Woodstock, Vermont back to Boston

After exploring the charming towns, scenic drives, and colorful landscapes of Vermont and New Hampshire, it’s time to wrap up your New England fall getaway and make your way back to Boston. The drive from Woodstock to Boston takes you through more classic New England scenery, making it a beautiful final stretch of your autumn road trip.

A road trip is truly the best way to experience fall in New England. The region comes alive during the autumn months, with vibrant foliage, charming small towns, and unforgettable landscapes around every corner. From the White Mountains of New Hampshire, to Salem’s spooky history, to the rolling hills of Vermont, this itinerary highlights some of the very best fall experiences New England has to offer.