Exploring Middlebury, VT: A Charming Gem Nestled in Vermont's Scenic Heartland

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Advisor - Gillian Spatz
Curated By

Gillian Spatz

  • Vermont

  • Active Travel

  • Arts & Culture

  • Off-the-Beaten-Path Travel

  • History

  • Architecture

  • Small Town

  • Local Culture

An aerial view of a autumnal town with mountains in the background.
Curator’s statement

Discover the enchanting allure of Middlebury, Vermont, a picturesque town nestled amid the rolling hills and verdant landscapes of the state's heartland. Steeped in history and surrounded by natural beauty, Middlebury beckons travelers with its quaint charm and vibrant cultural scene. From strolling along the idyllic streets lined with historic architecture to indulging in farm-to-table dining experiences, Middlebury offers a delightful blend of small-town ambiance and modern amenities. Whether you're seeking outdoor adventures in the surrounding countryside or immersing yourself in the town's rich cultural heritage, Middlebury promises an unforgettable escape for those craving an authentic Vermont experience. Join us as we delve into the treasures awaiting in this hidden gem of New England.

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Where to stay in Middlebury, VT

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Things to do in Middlebury, VT

A view of a brick farmhouse with a grassy meadow, trees and wooden carts in the surrounding areas.

Tour Middlebury College: Explore the picturesque campus of Middlebury College, known for its beautiful architecture and vibrant academic community.

Visit Shelburne Farms: Just a short drive away, Shelburne Farms offers stunning views of Lake Champlain, walking trails, farm animals and educational programs.

Hike the Trail Around Middlebury (TAM): Enjoy scenic walks or bike rides along this 16-mile trail that encircles the town, passing through forests, fields and alongside the Otter Creek.

Explore Middlebury's Downtown: Wander through the charming streets of downtown Middlebury, lined with boutique shops, art galleries and cozy cafés.

Take a Brewery Tour: Sample local craft beers at breweries like Drop-In Brewing Company and learn about Vermont's thriving beer scene.

Visit the Henry Sheldon Museum: Discover the history of Middlebury and Vermont through exhibits at the Henry Sheldon Museum, housed in an elegant historic building.

Kayak or Canoe on Otter Creek: Rent a kayak or canoe and paddle along the serene waters of Otter Creek, which meanders through Middlebury.

Attend a Performance at Town Hall Theater: Catch a play, concert or film screening at the Town Hall Theater, a community hub for performing arts in Middlebury.

Explore Middlebury Natural Foods Co-op: Browse local produce, artisanal goods and health foods at this beloved cooperative grocery store.

Ski at Middlebury Snow Bowl: In the winter, hit the slopes at Middlebury Snow Bowl, a family-friendly ski resort offering skiing, snowboarding and snowshoeing trails.

Visit UVM Morgan Horse Farm: Learn about the history and significance of the Morgan horse breed with a visit to this working farm and educational center.

Attend Middlebury Farmers Market: Experience Vermont's agricultural bounty at the Middlebury Farmers Market, held weekly during the warmer months, featuring fresh produce, artisanal foods and handmade crafts.

Day trips

Lake Champlain Islands: Explore the scenic beauty of Lake Champlain by taking a day trip to the nearby islands. Visit places like Grand Isle State Park for hiking and picnicking, sample local wines at a vineyard or simply enjoy the stunning lake views while driving or cycling around the islands.

Green Mountain National Forest: Immerse yourself in nature by venturing to the Green Mountain National Forest, just a short drive from Middlebury. Hike along picturesque trails, such as the Robert Frost Interpretive Trail, which winds through the forest and past the poet's former cabin. Marvel at waterfalls, wildlife and panoramic vistas as you explore this pristine wilderness.

Burlington: Experience the vibrant culture and eclectic charm of Burlington, Vermont's largest city, located about an hour's drive northwest of Middlebury. Stroll along the pedestrian-friendly Church Street Marketplace, visit the renowned ECHO Leahy Center for Lake Champlain to learn about the region's ecology or embark on a scenic cruise on Lake Champlain. Enjoy diverse dining options, boutique shopping and cultural attractions in this bustling college town.

Places to eat & drink in Middlebury, VT

Two pizzas on a platter on top of a wooden table with a metal gate in front of a fireplace in the background.

Morgan’s Tavern at the Middlebury Inn: Enjoy classic New England cuisine in a historic setting at this restaurant located within the Middlebury Inn.

American Flatbread: Indulge in wood-fired pizzas made with organic ingredients and topped with locally sourced produce and cheeses at this cozy eatery.

Two Brothers Tavern: Savor comfort food and creative cocktails in a relaxed atmosphere at Two Brothers Tavern, known for its hearty pub fare and friendly service.

Otter Creek Bakery: Start your day with freshly baked pastries, artisan bread and gourmet coffee at this beloved local bakery.

Fire and Ice: Experience interactive dining at Fire and Ice, where you can create your own stir-fry or pasta dish using a variety of fresh ingredients and sauces.

Costello's Market: Grab a sandwich, salad or gourmet snack at Costello's Market, a popular spot for quick and delicious meals made with quality ingredients.

Sabai Sabai Thai Cuisine: Explore the flavors of Thailand with authentic Thai dishes prepared with fresh herbs and spices at Sabai Sabai Thai Cuisine.

Swift House Inn: Dine in a historic inn setting at Swift House Inn, where you can enjoy refined American cuisine featuring locally sourced ingredients.

Middlebury Bagel & Deli: Start your morning with a freshly baked bagel topped with your favorite spreads or enjoy a hearty deli sandwich for lunch at Middlebury Bagel & Deli.

Need to know

Middlebury, Vermont, offers a wealth of experiences for visitors seeking a perfect blend of small-town charm, outdoor adventure and cultural enrichment. Whether you're exploring the historic streets of downtown, savoring farm-to-table cuisine at local eateries or immersing yourself in the natural beauty of the surrounding landscape, Middlebury captivates with its authenticity and allure. From the shores of Lake Champlain to the trails of the Green Mountain National Forest, the possibilities for adventure and discovery are endless. So, whether you're a history buff, foodie, nature lover or simply seeking a relaxing escape, Middlebury invites you to embrace the essence of Vermont and create lasting memories in this idyllic New England town.

Advisor - Gillian Spatz

Travel Advisor

Gillian Spatz

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Looking for more travel inspiration? Check out my guide, Austin Eats: Top Restaurants Defining the Capital's Cuisine. This guide is part of our ongoing series on travel to Vermont.