The Perfect 5 Day New England Fall Road Trip (New Hampshire and Vermont)

If a New England road trip in the fall is on your bucket list, you’re in the right place! New England is known for its charming small towns, epic hiking trails and some of the brightest fall foliage you’ll ever see. It’s no wonder so many people visit when the foliage is at its peak.

If it’s your first time visiting and you’re limited on time, I recommend exploring New Hampshire and Vermont. Both states are beautiful and have endless opportunities for leaf peeping, but they each have a distinct personality. To me, New Hampshire (specifically the White Mountains area) is better for hiking, while Vermont is better for exploring small New England towns that you may have seen in movies.

No matter where you go and what your itinerary is, New England feels magical in the fall. You’re sure to find something to love whether you’re a nature lover or you just enjoy a scenic drive and charming shops.

This itinerary provides all of my top recommendations if you have 5 days to spend in New Hampshire and Vermont. If you have more time, you can also check out my 7 day version of the itinerary. And if you’re also visiting Maine during your trip, make sure to check out my Acadia National Park itinerary as well.

This itinerary is based on my experience spending several weeks in New England in Fall 2022.

When is the Best Time to See Fall Colors in New England?

Peak foliage in Vermont and New Hampshire varies annually, making it challenging to plan a trip around the leaves. Generally, higher elevation areas experience foliage changes first, followed by the valleys. To maximize your chances of seeing the best colors, I recommend visiting anytime from the last week of September to the first two weeks of October. This window typically offers a great opportunity to experience the stunning fall colors in both states.

As your trip approaches, check the foliage trackers for Vermont and New Hampshire to find the best areas to visit. If witnessing peak foliage is essential, consider booking refundable stays and remain flexible. However, missing the exact peak day isn't a big concern, as foliage can vary due to lighting and time of day.

In 2022, peak foliage occurred around October 5th - 12th. I explored New Hampshire and Vermont from September 24th - October 10th and enjoyed stunning foliage in both states.

Where should you fly into for a New England road trip?

Most of the towns in New Hampshire and Vermont are quite small, so you’ll find a lot more flight options if you fly into Boston. Plus, it’s really not a far drive from Boston to all of the beautiful places in New Hampshire and Vermont.

For this New England road trip, you should fly into Boston and rent a car for the duration of your trip! If you want to explore Boston as well, I’ve also included some of the best things to do in Boston on day five of this itinerary.

New England Road Trip: 5 Day Itinerary Overview

• Day One: Fly into Boston, drive to New Hampshire and do a short hike if you have time.
• Day Two: Explore the White Mountains with a popular hike, a scenic drive and visit to the tallest peak in the Northeastern US.
• Day Three: Drive to Vermont and explore Stowe.
• Day Four: Tour a maple syrup farm and explore Woodstock.
• Day Five: Drive back to Boston and explore the city if you have time.

Day One

For day one, I suggest flying into Boston, renting a car, and driving to the picturesque New Hampshire White Mountains. This should take two to two and a half hours. Consider making a stop at a grocery store to stock up on hiking snacks and travel meals for added convenience.

When you arrive in the area, start with a short hike if you have time. Champney Falls, a 3 mile moderate hike to a unique waterfall, or Mount Willard, a 3.1 mile hike that leads to a stunning vista of a valley and Crawford Notch Road.

Where to Stay in the White Mountains

The White Mountains offer a couple of small towns where you’ll find numerous options for hotels and Airbnbs. For a centrally located stay, I personally recommend staying in Lincoln or nearby, which provides easy access to the Kancamagus Highway and Artist's Bluff. Consider the Holiday Inn Express & Suites for a comfortable standard option, or check out the Wilderness Inn Bed & Breakfast if you’re looking for something more unique.

Glamping enthusiasts will love Lumen Nature Retreat, offering A-frame and safari tents with all amenities. I’d love to check out this beautiful property during my next visit!

Read about one of my favorite glamping experiences in Moab, Utah.

Personally, I stayed in a modern cabin on Airbnb. It was located next to a river, pet-friendly and offered fast wifi for remote work.

Where to Eat in the White Mountains

Here are my favorite places to eat in the White Mountains of New Hampshire!

• StrEatz - A stationary food trailer with an eclectic menu featuring several vegetarian options.
• Cheese Louise - A delicious spot serving unique takes on - you guessed it - grilled cheese! This quirky eatery gets creative with their sandwiches by offering fixings such as BBQ shredded sweet potatoes, Nashville hot chicken, pesto and more.
• Gypsy Cafe - This homey restaurant offers food from all over the world. You’ll find Egyptian Brussel Sprouts, Malai Kofta, Indonesian peanut noodles and many more options.
• White Mountain Bagel Co - This convenient spot is the perfect place to fill up on a flavorful bagel breakfast sandwich and coffee during a day of hiking.

Day Two

Spend a full day exploring the New Hampshire White Mountains by doing an iconic hike and taking some epic scenic drives.

Hike to Artist’s Bluff at Sunrise

Artist’s Bluff is a popular and iconic trail in New Hampshire, offering stunning views of Echo Lake surrounded by vibrant fall foliage. It’s extremely popular, so I highly recommend visiting during sunrise on a weekday to avoid the crowds. Plus, the lighting is beautiful at sunrise!

The trail can be done in a couple different ways. The shortest version is to hike a half mile round trip beginning from the Cannon Mountain RV Park. However, you can also make the hike into a 1.5 mile loop trail that includes Bald Mountain.

I recommend adding on Bald Mountains because it’s less crowded and will offer you another beautiful view of the area.

Both trails involve some rock scrambling, so proper hiking shoes and water are essential. Despite the crowds, Artist’s Bluff remains a must-visit spot for stunning fall colors in New Hampshire.

Drive the Kancamagus Highway

You can’t go wrong with a scenic drive during a New England fall road trip and the Kancamagus Highway (nicknamed “The Kanc”) is one of the best there is. The route is 35 miles and connects Lincoln and Conway with numerous picturesque viewpoints along the way.

Be aware that there is a $5 fee for parking at the various stops along The Kanc highway. If you have an America the Beautiful pass, that will cover the fee. Other tips for driving the Kanc include to keep your distance from wildlife (you could see a moose!), not fly a drone within a quarter mile of the road (it’s against the rules) and be prepared to have little to no cell service.

Pro Tip: Download the Guide Along Audio tour of the Kancamagus Highway to learn about stops along the way while you're driving!

The best stops on The Kanc highway include:

• Hancock Overlook, Panoramic Overlook & Pemigewasset: Three overlooks that offer beautiful views of the surrounding mountains and fall colors.
• Lily Pond: Park on the side of the road and make a quick stop to see a calm pond. You’ll walk a few feet through the forest to reach the pond.
• Sabbaday Falls: An easy 0.7 mile trail that will lead to a unique waterfall. The water is a bright, turquoise color and it flows through a gorge that seems to make a right angle turn.
• Rocky Gorge: This area has a narrow gorge area where water flows and creates a waterfall in the Swift River. There is a bridge so you can see the waterfall from above.
• Lower Falls: Lower Falls is another beautiful waterfall that you shouldn’t miss while driving The Kanc. It’s a short walk from the parking lot. This is a great place for a picnic and popular for swimming during the summer months (exercise caution if the water is high).

There are several others to check out if you have enough time, but these are a great starting point! Read my full list of stops in my guide to the best things to do in the White Mountains.

Visit the Top of Mt Washington

At 6,288.2 feet, Mt. Washington is the highest peak in the Northeastern United States! With an elevation that high, it certainly offers breathtaking views on a clear day.

You can reach the summit via hiking, driving, or taking the unique Cog Railway, which climbs with a 25% grade. Since this is a quick itinerary, I recommend either driving or taking the Cog Railway.

I drove up the historic Mount Washington Road and loved taking in the views along the way. Note that it’s a steep drive and you’ll need to put your car in low gear when you drive back down so as not to overheat your brakes. The drive also has some steep drop offs.

At the top, there is plenty of space to walk around, a gift shop, a small museum area, a food court and more. You’ll also see a sign indicating where the fastest surface wind was ever recorded in the Northern and Western Hemisphere at 231 mph!

The weather can change rapidly at the summit and it’s not uncommon to experience high winds, fog and cold weather. Make sure to come prepared with warm clothing.

Day Three

Make your way from the White Mountains to Stowe, Vermont - a quintessential Vermont town that is beautiful in the fall.

If you’re interested in another scenic mountain drive, Mt Mansfield is the highest point in Vermont and offers beautiful views of the surrounding Green Mountains. You can either hike, drive or take the gondola to reach the top. I recommend trying to go early in the day, as the road closes early if they’ve reached capacity.

A few things to do in Stowe, Vermont include enjoying the view of the Stowe Community Church from Salon Salon, walking on the Stowe Recreation Path, visiting the nearby Moss Glen Falls, trying your luck at the Percy Farm Corn Maze and eating at Idletyme Brewing Company.

Other iconic places near Stowe include the Cold Hollow Cider Mill (they have delicious apple cider donuts and cider) and the Ben & Jerry’s Headquarters (they offer tours, or you can visit the gift shop and get ice cream).

Stowe is a gorgeous town and has a lot to offer, but expect crowds and a lot of traffic. It gets extremely busy during autumn.

Where to Stay in Stowe

Stowe has several hotels and Airbnbs to choose from, but be sure to book early to avoid the highest prices.

For a more affordable hotel that is still super chic and in a great location, check out the Field Guide Lodge. They have well-designed rooms and are within walking distance of downtown Stowe.

If you want to be in the center of downtown Stowe, check out Green Mountain Inn. This historic hotel has welcomed guests since 1833 and also has a nice restaurant.

Another place to stay near town is the Timberholm Inn. This cozy lodge offers outdoor amenities such as a fire pit and a hot tub and is the perfect place to stay if you’re looking for peace and quiet.

Day Four

Baird Farm

Drive south to another adorable Vermont town - Woodstock. Woodstock is located about an hour and a half south of Stowe. However, I recommend taking a detour to tour the Baird Maple Syrup Farm. This may easily become a highlight of your New England road trip!

Vermont is renowned for its abundant maple syrup production, surpassing all other states with over 2.5 million gallons in 2022. A quintessential Vermont experience is touring a maple syrup farm, and I highly recommend Baird Farm. This family-owned 560-acre farm in Chittenden, VT offers free tours that allow you to see their maple trees, sugarhouse and production process. Make sure to reserve your spot in advance!

During my tour with Jacob, I gained valuable insights into their process, witnessing a portion of their extensive collection tubes and syrup filtering. The highlight was sampling 7 distinct syrup types, including delightful infusions like a mint-infused syrup.

Situated less than 2 hours from Stowe and under an hour from Woodstock and Killington Peak, Baird Farm is a worthwhile addition to your Vermont itinerary. Whether you choose this farm or another, experiencing a sugarbush tour in Vermont is a must, and supporting a small business like Baird Farm is a rewarding choice if possible.

Explore Woodstock

After your tour of Baird Farm, explore the small town of Woodstock. Highlights include Mont Vert for coffee and pastries, a Maple Cremee from Woodstock Scoops and the Middle Covered Bridge.

2024 Update: Due to high crowd levels at the Sleepy Hollow Farm, the town of Pomfret will be closing the road off to non-residents from September 25 - October 16. Enjoy my photo and focus on the other beautiful places around Woodstock.

The most famous photo location is the Sleepy Hollow Farm. This privately-owned farm is a favorite of photographers who want to capture the feeling of fall in New England. The home is surrounded by rolling hills and features a rustic barn and peaceful lake. It’s a really popular place, so expect crowds. And make sure to abide by parking rules and only stay on the road while taking your photos.

Where to Stay in Woodstock

If you’re looking for an affordable stay in the heart of Woodstock, check out The Shire or The Vesper. The Shire is a cozy hotel that offers river views and The Vesper is a lovely family-owned bed & breakfast.

If you’re looking for something more quiet, look for a home outside of town. Check out this cozy cabin with mountain views and a firepit, or this rustic cabin right next to a stream.

Day Five

Spend your final day driving back to Boston to catch your flight. The drive should take about 2 and a half hours.

One option for a quick Vermont road trip stop (right on the way) is Quechee State Park, where you can enjoy a view overlooking the gorge. You can see it a short walk from the parking lot or enjoy a longer hike if you have time.

If you have time to explore Boston, here are some of the top things to do:

• Take a walk around the Boston Public Library Central Branch, which is known for its impressive architecture and massive size. Don’t miss Bates Hall!
• Have dinner in the North End, known as “Boston’s Little Italy.” One place I loved was Dino’s Cafe for their 16” Italian subs! It’s also worth trying a cannoli at Mike’s Pastry, Modern Pastry or both.
• Do some portion of the Boston Freedom Trail. If you only visit one spot, I recommend checking out the Granbury Burying Ground. Many famous figures in the American Revolution are buried here.

Final Thoughts

New England is a dream destination for a fall road trip, with its charming small towns, epic hiking trails, and vibrant fall foliage. New Hampshire's White Mountains are perfect for hiking enthusiasts, while Vermont's has some of the most picturesque small towns in the region. A New England road trip is the perfect way to embrace the enchanting magic of fall.

FAQ’s

Is a New England road trip worth it?

In my humble opinion, yes! New England is a beautiful part of the United States and has something for everyone, from outdoor activities to charming small towns to breathtaking scenery. I think that everyone should visit New England during the fall at least once in their lives.

How many days do you need in New England?

If you want to visit Vermont and New Hampshire, I recommend a minimum of 5 days so that you can properly experience the area. I also have a 7 day itinerary if you have a bit more time!

If you want to visit other New England states (Connecticut Rhode Island and Maine), I recommend adding more time. You can see a lot of Connecticut and Rhode Island by adding one day for each. If you want to add a visit to Maine and visit Acadia National Park, I recommend adding at least 4 more days to factor in driving time and seeing the park.

What are the must-do’s on a New England road trip?

• Go on a hike in the New Hampshire White Mountains
• Take a photo of the Sleepy Hollow House in Vermont
• Hike, drive or take the cog railway to the tallest mountain in the Northeastern US, Mt Washington
• Eat a maple creemee in Vermont
• Tour a maple syrup farm

What is the best month to visit New England states?

If you want to see the fall foliage, you should visit at the end of September or early to mid October. However, this area is beautiful to visit year round.

How crowded is New England in the fall?

Some areas covered on this itinerary get very crowded during peak foliage times. The most crowded areas I mentioned are Stowe, Vermont (the traffic gets bad as there aren’t a lot of alternatives) and the hike to Artist’s Bluff in the New Hampshire White Mountains.

As with any popular destination, plan accordingly to beat the crowds by getting an early start when you can, visiting on weekdays when possible and being patient. It is also advisable that you book your dinner reservations, hotels and activities early.

For more New England Travel Guides, check out these blogs:

• An Epic 10 Day New England Road Trip
• How to Spend One Day in Boston
• The Perfect 7 Day New England Road Trip
• The Best Hiking Trails in Acadia National Park
• The Best Day Hikes in the New Hampshire White Mountains
• The Best Things To Do in the New Hampshire White Mountains
• A Fall Guide for Acadia National Park
• The Perfect Day Trip to Connecticut

Thanks for Reading!