Unveiling The Best of New England: A Road Trip from Boston to Stowe, VT

For as long as I can remember, seeing the leaves change colors in New England has been on my bucket list of travel itineraries. I was finally able to make this trip a reality with a five-day road trip through New England with my sisters. If you are an eager traveler searching for an enchanting mix of picturesque beauty and historical significance, follow this road trip adventure from the bustling city of Boston to Stowe, VT.

Dotted with charming small towns, vibrant fall foliage, and majestic mountain views, this road trip provides an unforgettable jaunt through the heart of New England.

This post will guide you on the best route, along I-93 N and I-89 N, and reveal hidden gems for pit stops, such as the Quechee Gorge and Ben & Jerry’s ice cream factory.

Whether you’re a seasoned road tripper or new to the game, buckle up and embark on this captivating journey that seamlessly weaves culture and nature together.

I’ll show you how we fit five New England states into five days, beginning in Boston, Massachusetts.

Ready or not, here we come.

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Our road trip from Boston to Stowe, VT, began during the last week of September.

We flew to the East Coast into Boston Logan International. Boston is a great place to begin a New England road trip because it offers flights from many U.S. cities.

The rental car rates in Boston are often more competitive than the smaller New England cities, giving another reason to begin your road trip here.

The flight landed late evening, so we stayed at the Comfort Inn & Suites at Boston Logan.

It’s a clean hotel that offers a complimentary shuttle from the airport. Plus, we only needed it for a good night’s sleep. As a bonus, it provides a complimentary breakfast.

What to Do in Boston

I suggest starting your day trip from Boston to Stowe, VT, early to see all the highlights.

If this is your first time visiting Boston, use the Hop-On, Hop-Off bus to see the sights. This tour is a great way to see many places without maneuvering the city streets. It’s also easy to visit many places in a short amount of time.

Trip Tip: Save Boston for another trip and head straight to Vermont.

With such a rich history, you’ll want to dedicate at least a full day in Boston to scratch the surface of its rich architecture and historical spots.

How Far is Stowe from Boston?

As a first-time visitor to New England, you might be curious about the distance you’ll cover.

Boston to Stowe, VT, is roughly 217 miles, which isn’t too bad.

On a good day, you can expect to reach Stowe in about 3.5 to 4 hours.

And let me tell you, the drive is as scenic as they come, especially during fall. Those New England autumn hues are truly something to behold!

How to Get From Boston to Stowe VT

Say goodbye to the hustle and bustle of city life as you take the most scenic drive from Boston to Stowe, VT. Leave the city’s traffic behind and drive towards the rolling hills and cute little towns of Vermont.

The road trip to Vermont is effortless in the fall. While this is the route we took and thoroughly enjoyed, I highly recommend checking and planning your own specific route before you hit the road.

Consider my trip planner as inspiration, not exact directions, as I don’t want any adventurers getting lost! I’ve included approximate travel times, but exact driving times may vary.

Boston to Concord, NH (1h 15min, 68 miles)

Start your journey by heading north on I-93N from Boston. Enjoy vibrant fall colors as you drive toward New Hampshire’s state capital.

Take a break to explore historic downtown Concord, which boasts charming shops, cafes, and plenty of foliage. Visit the New Hampshire State House for a photo op.

Trip Tip: You want GPS and a Google printed map or paper directions. Having your directions printed out will help in places where you do not have internet.

Concord to Quechee Gorge (1h 25min, 85 miles)

Continue on I-89N, passing through picturesque towns like Sunapee and Lebanon. Stop at Quechee Gorge, Vermont’s “Little Grand Canyon,” for stunning views.

Quechee Gorge to Woodstock, VT (20min, 14 miles)

Proceed west on US-4 to reach Woodstock, VT, a quintessential New England town that’s perfect for a fall visit. Enjoy antique shops, historic homes, and vibrant leaves.

There are many Instagram-worthy spots in Woodstock.

The covered bridges, the Sleepy Hollow Farm, Sugarbush Maple Syrup Farm, and the Mont Vert cafe should top your list of places to see and are only minutes away from each other.

Woodstock to Taftsville Covered Bridge (10min, 4 miles)

Don’t miss the nearby Taftsville Covered Bridge, a red, two-span bridge built in 1836.

The covered bridges along your route from Boston to Stowe, VT make great spots for photos and taking in the autumn ambiance.

The route that takes you to picturesque Sleepy Hollow runs right through the Taftsville Bridge, one of Vermont’s oldest covered bridges and one of many covered bridges in Vermont.

There isn’t much to do at the covered bridges other than hop out of the car and take a pic, but they are still beautiful.

Taftsville Covered Bridge to Sleepy Hollow Farm (20min, 7 miles)

Head north on VT-12 to Sleepy Hollow Farm, an iconic pastoral scene ideal for a leisurely stop. Capture the fall foliage and beauty of the farm.

It is a privately owned property by Aerosmith’s guitarist Joe Perry and his wife, and it is gorgeous. You can’t walk onto the property, but you can pull off to the side of the road for pictures.

If you are an Instagram fan or follow any New England boards on Pinterest, you have most likely seen this highly photographed farm.

Sleepy Hollow Farm to Sugarbush Farm (15min, 6 miles)

Next, continue up VT-12 to the Sugarbush Farm. It is a large working farm with multiple barns and many animals.

Delight your taste buds with their famous maple syrup and sample their delicious cheeses surrounded by vibrant fall colors.

There is a charming gift shop that sells Vermont state ornaments and our most unique buy of the trip, CBD oil from Kingdom Acres. My sister, Jenny, still swears this works better than anything else she has tried for her chronic heel pain.

Unfortunately, with our excursion in Boston, we couldn’t make it to the adorable and much-anticipated Mont Vert Cafe before it closed. It is still on my list; hopefully, I will get there next time.

Trip Tip: Plan to stay overnight at the Woodstock Inn. The town is charming and deserves more time.

More to Explore in Woodstock, VT.

As you go from Boston to Stowe, VT, you may want to plan an overnight stay in Woodstock, the quintessential New England town. With so many things to see, you’ll see why Its charm lies in beautiful, historic architecture, including the Billings Farm and Museum.

If time allows, explore the Green, the heart of the town, showcasing its rich history with centuries-old homes and shops. Fall offers a mesmerizing color display in the surrounding trees.

The beautifully restored Woodstock Inn, the town’s crown jewel, offers delicious local cuisine.

The serene aura and compelling history make Woodstock a special town to visit.

Before leaving, stop at the Woodstock Farmer’s Market to see all the flowers, pumpkins, and apples on full display. Stock up on baked goods in the bakery and grab some fresh food.

Pick up a snack for the remaining part of your road trip from Boston to Stowe, VT, including their turkey, apple, and cheese sandwich. Have you ever heard of such a thing? It is such an unusual but delicious combination. 

Sugarbush Farm to Ben and Jerry’s Ice Cream Factory (1hr 12min, 57 miles)

Head north on I-89 to the famous Ben and Jerry’s Ice Cream Factory. Take a tour, learn about their history, and enjoy a scoop.

Ben and Jerry’s Ice Cream Factory to Stowe, VT (20min, 11 miles)

Finish your Boston to Vermont road trip by heading to Stowe, VT.

Enjoy a cozy mountain town atmosphere, breathtaking foliage, scenic drives like Smugglers Notch State Park, and many outdoor activities.

Toast Your Road Trip from Boston to Stowe, VT

End your road trip experience from Boston to Stowe, VT, at the local wine and cheese shop, Dedalus, and toast to a beautiful drive.

You’ll most likely be exhausted from the day as you settle in, only to wake up and hit the road again the next day.

To read about our day in Stowe, check out my post, The Perfect Visit to Stowe, Vermont in the Fall.