The Best Places to Visit on a Trip Between Bennington, Vermont and Boston, Massachusetts

Are you planning a road trip between Bennington, Vermont and Boston, Massachusetts? Here are our top five places to visit during the journey!

Route Highlight

Before we dive into our top five places, let's highlight the beautiful route you'll be driving. This trip takes you through scenic New England countryside, filled with charming small towns, rolling hills, and stunning autumn foliage. Be prepared for a picturesque drive!

1. Manchester, Vermont

Located in the heart of the Green Mountains, Manchester offers both natural beauty and historic charm. Visit the Hildene Estate, once the home of Robert Todd Lincoln and his family, and tour the 1903 Georgian Revival mansion and beautiful gardens. Wander through the Northshire Bookstore, one of the best independent bookstores in the country, and grab a coffee at Spiral Press Cafe.

2. Keene, New Hampshire

Keene is a small town with a big personality. Head to the Monadnock Food Co-op, a member-owned grocery that specializes in local, organic, and sustainable products. Walk through Central Square, where you'll find bustling farmers markets, craft fairs, and live music events. And don't miss the annual Pumpkin Festival in October, where Keene sets the world record for the largest number of lit jack-o'-lanterns!

3. Worcester, Massachusetts

As the second-largest city in New England, Worcester has plenty to offer. Visit the Worcester Art Museum, a world-renowned museum with a collection of over 38,000 works of art. Check out the Worcester Public Market, a vibrant indoor market featuring local vendors and delicious food. And if you're a fan of architecture, don't miss the Worcester City Hall, a stunning Renaissance Revival building.

4. Concord, Massachusetts

Concord is a town steeped in American history. Visit the Concord Museum, where you can learn about the town's role in the Revolutionary War and see artifacts like Henry David Thoreau's desk and Ralph Waldo Emerson's study. Walk through Walden Pond State Reservation, where Thoreau famously lived in a cabin for two years and wrote his masterpiece, Walden. And explore Sleepy Hollow Cemetery, where you can find the graves of Thoreau, Emerson, and Louisa May Alcott.

5. Lexington, Massachusetts

Another Revolutionary War hotspot, Lexington is a must-visit for history buffs. Take a tour of the Lexington Battle Green, where the first shots of the war were fired. Visit the Buckman Tavern, a historic building that served as a gathering place for the Lexington Minutemen. And if you're looking for a sweet treat, stop by Wilson Farm, a local farm stand that sells fresh produce, baked goods, and homemade ice cream.

Conclusion

Whether you're interested in history, nature, or just a good book and cup of coffee, this road trip has something for everyone. From Vermont to Massachusetts, you'll find plenty to explore and enjoy along the way. Happy travels!