Boston to Bennington: A Journey Through Farms and Fields

Retreat Farm is your perfect introduction to the Vermont experience, blending scenic outdoor spaces with agricultural heritage. Wander through miles of walking trails, including a moderate one-mile interpretive trail. The farm store offers local goods, and the natural “forest playground” is a great spot for all. Among the friendly farm animals, you'll meet pigs, goats, and the star of the show: Carlos the Ox.
On Saturdays (and select Fridays), you can also take a guided tour around the farm to learn some interesting facts from its history and interact with the animals. To book a tour and check the schedule, please visit the official website.

Head to the brick-lined downtown of Brattleboro, Vermont, and make your way to the Works Café. Situated on the town's main street, this breakfast spot and bakery is known for its classic breakfast and lunch bowls, as well as various smoothies.

The Molly Stark Scenic Byway winds its way to the top of Hogback Mountain, revealing fantastic views of Molly Stark State Park and the surrounding landscape. Be sure to stop at the observation deck to take it all in.

Celebrate your arrival in Bennington, Vermont, by visiting the Bennington Battle Monument. This splendid stone tower, built to commemorate the 1777 turning point in the American Revolutionary War, stands as the tallest man-made structure in Vermont at 306 feet. When open, the observation deck offers sweeping 360-degree views spanning Massachusetts, Vermont, and New York. Additionally, guests can stroll the grounds and learn about the other statues and monuments on site.
Please note that the Monument has seasonal opening times, you can check the schedule on the official website.

This family-friendly pizza parlor is not only known for its irresistible garlic knots (bet you can't eat just one!) but also offers pizzas by the pie or slice, alongside salads, sandwiches, and pasta dishes. Kick back in a booth and catch a game, or enjoy the outdoor picnic tables during the summer.

The Four Chimneys Inn is one of the lodging options in Bennington that really captures the spirit of southern Vermont. Situated in a historic country home, this bed and breakfast offers inviting rooms and a lounge with scenic views. In the morning, you’ll be treated to a hearty breakfast to kick-start your day.