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 early August.

Whether you are 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 in Vermont, New Hampshire and Massachusetts.

This 7 day New England fall road trip focuses on staying for multiple nights in one hotel that’s 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 one night, the second hotel for two nights and three nights at the last hotel.

A planned fall road trip or a more flexible itinerary

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 can find the best places unexpectedly.

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 destinations and places at lower altitude.

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.

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 is also common during the fall in New England. A good rain jacket and shoes are a must! When I’m visiting the charming towns in New England I like to look put together but appropriate for being in nature. My go-to choice for a raincoat is this and for waterproof shoes that still look cute I opt for these.

Day 1 – 2 Salem, Massachusetts

The first stop on your 7 day New England fall road trip is Salem, Massachusetts. 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 sad events and remembering the victims, while also leaning into the spooky fun that the symbol of witches conjure 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. When you arrive in Salem, 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.

The best things to do in Salem, Massachusetts

After brunch, you’re already 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 you’re heading next.

Essex Street is closed to cars and lined with restaurants, stores and attractions. This is the hub of Salem activity. Essex Street is also where you will find the Peabody Essex Museum. The museum has an ongoing exhibition covering The Salem Witch Trials of 1692 and starting on September 14, 2024 they will open a new exhibit entitled Conjuring the Spirit World: Art, Magic and Mediums.

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.

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 shop that has great witchy gifts and crystals. I’ve also gotten a tarot card reading at Ascend and it was a fun experience.

Just off of Essex Street you’ll find two of my favorite stores in Salem, HausWitch and Oak and Moss. HausWitch is a great store to learn about and purchase crystals, candles and other cute witchy home items. In October 2024 HausWitch offered aura readings which was a very fun experience! Oak and Moss also sells beautiful home goods and gifts as well as plants.

Hotel recommendations in Salem, Massachusetts

After you’re done exploring the shops around Essex Street, it should be time to check into your hotel. Salem has great boutique hotel options, like the beautifully appointed and historic Merchant Hotel (George Washington stayed here!), but my favorite hotel in Salem for first time visitors is The Hawthorne Hotel.

This historic property is located at one end of Essex Street (the opposite end from Gulu-Gulu), so it’s in the center of all the action. The Hawthorne Hotel is named after famed Salem resident and author, Nathanial Hawthorne. The home that one of Hawthorne’s most famous works, The House of Seven Gables, is based on is located a few blocks away and is open for tours.  The Hawthorne Hotel was established in 1925 and is a member of the Historic Hotels of America. It’s also known to be haunted!

After you check into The Hawthorne Hotel walk to Notch Brewery for some lite bites and local beers. Notch is located along the South River and has a taproom and a beer garden. After sampling the local brews, it’s time for a walking tour.

While walking tours are offered all day long in Salem, I like to do them in the evening or after dark as that time of day lends itself to the ghost stories you will likely hear on your tour. Salem is a great place to take a tour because it’s such a walkable city. There’s so much to see in Salem, a tour makes it easy to fit everything in while also learning about the history.

There are many different tour operators and types of tours in Salem. From tours that focus on the Witch Trials history to kitchy ghost tours to Hocus Pocus themed tours (parts of the movie were filmed in Salem), so there’s something for everyone. I like a tour that combines history with fun ghost stories. Some of my favorite Salem tour operators are Witch City Walking Tours, Spellbound Tours and Black Cat Tours.

I recommend taking a look at the different tour offerings and picking one that best fits your interests. Most of the tours cover the big sites in Salem – The Witch House (the only structure still standing with direct ties to The Salem Witch Trials), The Ropes Mansion (a historic, and haunted, home in Salem that was the setting of Allison’s house in Hocus Pocus) and Old Burying Point and the Salem Witch Trials Memorial which is also known as Charter Street Cemetery. These locations are all must-dos in Salem, so if they aren’t included in your walking tour itinerary I recommend you visit them on your own.

Dinner in Salem, Massachusetts

For dinner in Salem, I love Bambolina which has a menu focused on hand-made pizza. After dinner I recommend having a night cap at Rockafella’s which is a casual restaurant and bar that’s known to have a spooky history (ask your server about the “lady in blue”) or at Flying Saucer Pizza Company which has a long list of spooky themed cocktails. If you prefer something sweet rather than a drink, Goodnight Fatty has incredible homebaked cookies.

Days 2 – 4 Bretton Woods, New Hampshire

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 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 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

Artists Bluff is about 18 miles from The Omni. It is one of the best fall hikes in the area. It’s a relatively easy and 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 2024, 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.

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.

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.

Bretton Woods Ski Gondola is a scenic gondola ride located by the resort. 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 – 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.

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.

Days 4 – 7 Woodstock, Vermont

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. I recommend having breakfast at The Omni and then hitting the road. 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.

Exploring downtown Woodstock, Vermont

Your room may not be ready yet, but that’s ok. Leave your bags and set off to explore downtown Woodstock. One of the main reasons I love The Woodstock Inn and Resort so much 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.

If you’re hungry for lunch I recommend grabbing a sandwich at Mon Vert Cafe, a six minute walk from the resort. Spend the afternoon going in the shops along the two main roads, Central Street and Elm Street. There’s so much to see, including Vermont’s longest running independent bookshop, The Yankee Bookshop. I also love shopping in Vermont Flannel, 37 Central Clothiers, Woody’s Mercantile and F.H. Gillingham and Sons.

After you’re done exploring downtown Woodstock, go back to the resort to freshen up and get ready for your evening. Grab cocktails from the bar at The Woodstock Inn’s main restaurant, Red Rooster, and take them outside to enjoy in the Adirondack chairs on the resort’s beautiful front lawn.

When you’re done with your cocktails, walk back down Central Street and have dinner at Melaza Bistro. Melaza is a restaurant that focuses on Caribbean tapas and entrees. I love their vegetarian paella! If you have room after dinner, grab a Vermont delicacy, the Maple Creemee ice cream, from Vermont Scoops.

Woodstock to Stowe, Vermont

For your first full day 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.

I like walking around Stowe’s main shopping street, Main Street. You can also tour the nearby Ben & Jerry’s Factory and check out a 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.

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.

When you’re done exploring Stowe, drive back to Woodstock and grab dinner at Richardson’s Tavern, the casual pub in The Woodstock Inn.

Maple syrup farms and fall hikes near Woodstock, Vermont

On your final day in Vermont, pick up a quick breakfast and coffee to-go at Mon Vert, or opt for a more leisurely meal at Red Rooster in The Woodstock Inn. Start your day with a fall foliage hike – The Pogue and Mount Tom trail. This hike is moderately difficult and takes around two hours to complete. After the hike, grab lunch in town at Soulfully Good Cafe where they have great sandwiches, salads and soups.

Next, head to local cheese and maple syrup farm, Sugarbush. This farm is situated in the mountains on 500 acres and the views are spectacular. You can check out the cheese work room, walk the maple trail and buy Sugarbush products at the gift shop. From Sugarbush, head to a local brewery. Some of the best breweries in the area are Long Trail, Harpoon and River Roost.

For dinner check out Worthy Kitchen which is a restaurant that focuses on farm-to-table comfort food and local craft beers. Their sandwiches are popular and people love the burgers and chicken sandwiches. I always opt for their falafel burger. Worthy Kitchen is a very popular spot and I recommend using Resy to book a table ahead of time.

After dinner grab drinks at Au Compoir, an incredibly chic cocktail bar located just a few minutes walk from The Woodstock Inn. This modern craft cocktail bar serves delicious drinks and small plates. I always like checking out their seasonal cocktail list!

A road trip is the best way to experience the fall season in New England. This region really comes alive during the autumn months and a road trip is the best way to see the most of the fall beauty. This travel itinerary for the perfect fall road trip in New England should serve as your guide to see the best that the area has to offer!