Tour Guides & Itineraries

June in Bennington, Vermont: Outdoors, Art, Music & Summer Energy

The benches are back out. The flowers are blooming along Main Street. Trails are filling with hikers, rivers are moving steadily again, and outdoor dining returns to sidewalks, patios, and

May in Bennington, Vermont

Spring Energy, Outdoor Events, and the Start of Something Good May is when Bennington fully opens up. The doors, the streets, the stages, all of it. After a long Vermont

April in Bennington, Vermont: Spring Returns with Art, History, and Fresh Air

April in Bennington feels like a turning point. Snow gives way to longer days, mountain views begin to soften into spring, and the town’s arts and cultural spaces reopen their

March in Bennington, Vermont

When Winter Sweetens & Spring Begins to Stir Maple Steam, Green Celebrations, and a New Theater Season March in Bennington feels alive. The steam starts rising from sugarhouses. Storefront windows

A Romantic Getaway Begins Here: Fall in Love with Bennington, Vermont

Some places try to manufacture romance. Bennington simply lives it. It’s in the way Main Street invites you to slow down and wander hand in hand. It’s in the quiet

10 reasons to visit Bennington, Vermont in 2026

Welcome to Bennington, Vermont, a town where history, art, culture, and outdoor adventure come together in perfect harmony. Located in the rolling hills of southwestern Vermont, Bennington offers a quintessential

Celebrate the Holidays in Beautiful Bennington, Vermont

Your Guide to a Festive December There’s nothing quite like December in Bennington. Snow-covered evergreens, warm lights twinkling along Main Street, and the kind of small-town charm that makes the

October in Bennington: Foliage, Festivals, and Family Fun

The air is crisp, the leaves are turning, and Vermont is settling into one of its most beloved seasons. Fall in Bennington is a time for scenic drives, apple picking,

Fall foliage in Bennington, Vermont featuring the Bennington Battle Monument

Foliage, Flavor, and a Scenic Escape in Bennington, Vermont

September Itinerary and Fall Recommendations Fall in Vermont is never just about the leaves; it’s about the journey, the food, and the traditions that make this season unforgettable. In Bennington,

Experience History: Bennington’s 2025 Battle Day Weekend

Battle Day Weekend Kicks Off in Bennington! Bennington has been honoring the Battle of Bennington for nearly 250 years, making it one of the nation’s longest continuously celebrated Revolutionary War