Historic Downtown


Seen from above, a rural town nestled among trees and a bridge spanning a river.
People sit at tables under canopies outside beside old brick buildings on a warm day.

Middlebury, Vermont

Nestled in the rolling hills and idyllic farmlands of Addison County, Otter Creek runs through Middlebury’s literary history, including Robert Frost’s homestead drawing writers and artists. Nearby, Middlebury College and its Snow Bowl ski area offer both outdoor recreation opportunities and a deep dive into history and art. The area also offers standout cycling roads and a trail that wraps around the town. 

A small creek winds through woods in the winter and a placard sits in the foreground.
A snowy path winds through the woods in the winter.

Robert Frost Interpretive Trail

Among Vermont’s most notable poets, Robert Frost spent summer and fall every year at his Ripton home, the Homer Noble Farm. In Shaftsbury, Vt., he wrote his famous “Stopping By Woods on a Snowy Evening.” The Robert Frost Interpretive Trail commemorates the U.S. Poet Laureate’s work and offers inspiration and sweeping views.

An orchestra plays on stage while a movie is projected on a screen behind them.

Middlebury New Filmmakers Festival

Annually in August

Supporting, promoting, and exhibiting the work of first- and second-time filmmakers, the festival showcases film from around the world in nearby Leicester.

View of the colorfully painted Middlebury train station from behind a fence. The building is teal with large pink flowers painted along the side of it.

Take the Train to Middlebury

A car-free vacation to Middlebury includes local baked goods and seasonal dining, immersive art exhibits and displays, and time to explore nature paths.

Eat, Shop, and Stay in Middlebury







Transportation Options

For Middlebury

Amtrak Station 
30 Middle Seymour Street
Middlebury, VT 05753  

Local Transportation   

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Discover More

Trip planning resources with Middlebury’s local downtown organization.

Experience Middlebury about Discover More