Best Things to Do in Middlebury, VT

You want to know the best things to do in Middlebury. You can stroll Historic Downtown, taste local flavors along the Middlebury Tasting Trail, or hike the Trail Around Middlebury. If you ask what to see, check out the Henry Sheldon Museum, Middlebury College Museum of Art, and Town Hall Theater. For outdoor fun, visit Branbury State Park or ski at Middlebury Snow Bowl. Experience Middlebury through its local shops, horse farm, and vibrant food scene. You will find the best things for every interest.

• Must-see spots include:

  • Historic Downtown Middlebury

  • Middlebury Tasting Trail

  • Henry Sheldon Museum

  • Trail Around Middlebury

  • Middlebury College Snow Bowl

Key Takeaways

• Explore Historic Downtown Middlebury for unique shops, local restaurants, and beautiful views of Otter Creek.

• Experience the Middlebury Tasting Trail to sample local wines, ciders, and spirits from various producers.

• Enjoy outdoor activities like hiking the Trail Around Middlebury or skiing at Middlebury Snow Bowl for year-round adventure.

Best Things Downtown

Downtown Middlebury invites you to explore a lively mix of history, culture, and local flavor. You can walk everywhere, discover unique shops, and enjoy the sights and sounds of Otter Creek. Here’s what you should not miss when you visit downtown.

Main Street & Otter Creek

Main Street sits at the heart of Middlebury. You can stroll along the sidewalks and find everything from cozy cafés to local restaurants. The Otter Creek area gives you beautiful views and a sense of the town’s past. If you stand on the west side of the Main Street Bridge, you get a perfect view of Middlebury Falls. The sound of rushing water and the sight of old mill remnants make this spot special.

Tip: Bring your camera for photos of the falls and the historic bridges.

You can also find some of the most highly rated spots right on Main Street and near Otter Creek:

• Otter Creek East (Bakery & Deli)

• Taste of India (Indian restaurant)

• Two Brothers Tavern (classic pub fare)

• Yogurt City (frozen yogurt shop)

• Crooked Ladle (dining, bar, catering)

• Middlebury Marquis (movie theater and Mexican cuisine)

• Vermont Book Shop (independent bookstore)

Main Street holds a lot of history. Here’s a quick look at some important sites:

You can feel the town’s history at the busy intersection of Main, Park, College, and South Streets. This spot has shaped Middlebury’s growth for over fifty years.

Henry Sheldon Museum

You will find the Henry Sheldon Museum right in downtown. This museum stands out among Vermont museums for its deep connection to local life. Step inside and you’ll see exhibits that bring Middlebury’s story to life. The current exhibit, “From Homespun to Couture: Fashion in Historic Middlebury,” shows off vintage hairstyling, fabric mending, and knitting. You can also see Vermont furniture, paintings, and artifacts from famous Vermonters.

You can also enjoy special features like the Downtown Middlebury Portrait, which shows over a hundred oil portraits of local people. The Annual Holiday Train Exhibit delights families every year. The Stewart-Swift Research Center makes Middlebury one of the best-documented towns in New England. If you love museums, this is a must-see.

Middlebury College & Art Museum

Middlebury College sits just a short walk from downtown. The campus feels open and welcoming. You can visit the Middlebury College Museum of Art for free. The museum offers changing exhibits, lectures, and family-friendly programs. You might catch “Giovanni Battista Piranesi: Visions of Grandeur” or see the “Le Petit Salon” exhibit, which brings a piece of 18th-century Paris to Vermont.

You can also explore the campus’s public sculpture collection, which features 25 artworks outdoors. Guided tours are available if you want to learn more. The museum has restrooms and kid-friendly activities, so families feel welcome. Parking is easy and free.

Note: The art museum and campus are open to all. You can enjoy the art, the green spaces, and the college’s lively atmosphere.

Local Shops & Galleries

Downtown Middlebury has a great mix of shops and galleries. You can browse for gifts, books, art, and outdoor gear. Here are some favorites:

• Junebug and Round Robin (thrift shops supporting local health services)

• Otter Creek Used Books (gently read novels)

• Stone Leaf Teahouse (imported loose-leaf teas)

• Sweet Cecily (modern country gifts and handmade treasures)

• Middlebury Mountaineer (outdoor gear and rentals)

• Jackson Gallery at Town Hall Theater (art gallery)

• PhotoPlace Gallery (fine art photography with monthly exhibits)

You can also visit Edgewater Gallery for rotating art shows. Right now, you can see “Earthen Gestures.” Soon, “Reclaimed” will open, featuring new works. Many shops offer art supplies, branded merchandise, and community gallery spaces. You can find everything from sketchbooks to Vermont-themed T-shirts.

Tip: Take your time exploring. Many shops and galleries feature work by local artists, so you get a real sense of Middlebury’s creative spirit.

You will find that downtown Middlebury offers something for everyone. Whether you want to shop, eat, see art, or just enjoy the view, you can do it all within a few blocks.

Middlebury Outdoor Activities

You want to get outside in Middlebury. This area gives you so many ways to enjoy nature. You can hike, bike, swim, or ski. The best hiking and biking trails, lakes, and parks are all close by. Here’s what you can do for your next outdoor adventure.

Tip: Spring is the best time for hiking in Middlebury. You get warmer weather, beautiful views, and fewer crowds.

Trail Around Middlebury (TAM)

The Trail Around Middlebury, or TAM, is a favorite for locals and visitors. You can walk, run, or bike this 18-mile loop. The trail circles the town and connects you to forests, fields, and the banks of Otter Creek. You will find easy to moderate sections, so everyone can enjoy it.

You will see a lot of wildlife and natural features on the TAM. Look for a suspension bridge over rushing falls and a dam on Otter Creek. Some paths are soft with pine needles, while others have gravel for easy walking. Wooden signs show you where beavers live and help you spot trees like yellow birch and sugar maple. You can walk through farm fields and meadows filled with wildflowers. Near a small pond, you might see many birds. The nature preserve around Otter Creek and Wright Park is perfect for exploring. You get great views of the ravine as you walk upstream.

Rikert Outdoor Center

You want to try winter sports? Head to Rikert Outdoor Center. This spot is popular for cross-country skiing, snowshoeing, and snow biking. The center sits in the Green Mountain National Forest, so you get beautiful scenery with every visit.

You can rent gear at the center. The trails are well-groomed and marked. Families and beginners feel welcome here. If you visit in winter, Rikert is a must for outdoor fun.

Lake Dunmore & Branbury State Park

Lake Dunmore is a top spot for swimming, boating, and relaxing. Branbury State Park sits right on the lake and gives you easy access to the water. You can rent a canoe, launch your boat, or fish for bass and trout. The park has a private beach with a dock and chairs, so you can relax by the lake.

1. Canoe rentals at Branbury State Park.

2. Boat launch for easy access to Lake Dunmore.

3. Fishing for many species in the lake.

You can hike the Mount Moosalamoo Trail or explore the Moosalamoo National Recreation Area. The park also connects you to the Green Mountain National Forest, which has more trails for hiking and biking. Bring a picnic and enjoy the view. You might spot wildlife in the woods or along the shore.

Middlebury Snow Bowl

If you love skiing, you need to visit Middlebury Snow Bowl. This ski area is small but packed with fun. You get 150 skiable acres and up to 200 inches of snow each year. The Snow Bowl has 17 to 25 trails, so you can find runs for every skill level. The vertical drop is 1,000 feet, which gives you a real thrill.

• Skiable Acres: 150

• Average Annual Snowfall: 150–200 inches

• Number of Trails: 17–25

• Vertical Drop: 1,000 feet

You can ski, snowboard, or just enjoy the mountain views. The Snow Bowl is great for families and beginners. You can rent gear on site. Winter is the best season for this adventure.

Lake Champlain

Lake Champlain is a short drive from Middlebury. This huge lake offers even more outdoor activities. You can swim at public beaches, launch your boat, or hike in state parks. Many parks have day use and overnight options. You can also visit wildlife management areas for birdwatching or hunting.

You can find more hiking and biking trails near the lake. The Green Mountain National Forest is close by, so you can plan a full day of adventure. Bring your camera for the lake views and sunsets.

Note: Spring is the best season for hiking in Middlebury. You get warm weather and fewer people on the trails.

You will find that Middlebury gives you endless options for outdoor fun. You can hike, bike, swim, or ski. The lakes, trails, and forests make this area a top spot for adventure in Vermont.

Vermont Food & Drink

You want to taste the best of Middlebury. This town gives you plenty of choices for breakfast, lunch, and dinner. You can start your day at Haymaker Bun Company, a breakfast spot known for specialty brioche buns. For lunch, you might visit Dakin Farm for Vermont maple sausage or Champlain Valley Creamery for handcrafted organic cheese.

Middlebury Tasting Trail

You can explore the Middlebury Tasting Trail for a true Vermont drink experience. The trail includes stops like Lincoln Peak Vineyard, Woodchuck Hard Cider, Stonecutter Spirits, Appalachian Gap, Otter Creek, Whistle Pig Whiskey, and Drop-In Brewing. You get to sample beer, cider, whiskey, gin, and wine. Each stop offers something different, so you can find your favorite.

• Lincoln Peak Vineyard: Five types of wine

• Woodchuck Hard Cider: Flight of cider samples

• Stonecutter Spirits: Single barrel gin, whiskey

• Appalachian Gap: Whiskey, tequila, rum, coffee liqueur, gin

• Otter Creek: Beer and food menu

• Drop-In Brewing: Seven beers, rotating taps

Lincoln Peak Vineyard

Lincoln Peak Vineyard stands out for its award-winning wine. You can taste the Ragtime line and other popular wines. The vineyard earned dozens of medals and won Winery of the Year in 2016. You get a relaxed setting for lunch or dinner with beautiful views.

Local Breweries & Cideries

Middlebury has top-rated breweries and cideries. You can try Woodchuck’s Campfire Pancakes cider, Drop-In Brewery’s Red Chair beer, Otter Creek Brewing Co’s Couch Surfer beer, and The Shed Brewery’s Fresh Slice. Many restaurants serve these local drinks with dinner.

Farmers Market

You can visit the Middlebury Farmers Market year-round. You find local organic produce, cheese, breads, bakery items, and crafts. The market runs outdoors in warm months and indoors in winter. You get fresh options for breakfast, lunch, or dinner.

Farm-to-Table Dining

You want a unique dinner spot? Try Middlebury Natural Foods Co-op. This member-owned co-op focuses on local ingredients and healthy food. You get a true Vermont farm-to-table experience for breakfast, lunch, or dinner.

Tip: Many restaurants in Middlebury offer outstanding food, attentive staff, and beautiful settings. You can enjoy dinner at Jessica’s at the Swift House or try Norbert for a relaxed evening.

Visiting Middlebury Tips

UVM Morgan Horse Farm

You can visit the UVM Morgan Horse Farm for a unique experience in Vermont. The farm offers guided tours where you meet and interact with Morgan horses. You walk the scenic grounds and learn about the first horse breed developed in the United States. The farm started in 1878 and played a role in American history, including the Civil War and the Pony Express.

Events & Festivals

You find plenty of events and festivals when visiting Middlebury. The town hosts the Memorial Day Parade, Circus Smirkus, Foodaroo, and the Festival on the Green. You can join the Middlebury New Filmmakers Festival, Middlebury Maple Run, and Middlebury Pride. The Very Merry Middlebury celebration fills the holiday season with cheer.

46th Annual Middlebury Summer Festival on-the-Green: Join a week of free, family-friendly performances from July 13–19, 2025. Enjoy live music and community spirit under the big white tent on the Village Green.

Day Trips Nearby

You can plan day trips from Middlebury to explore more of Vermont. Visit Waterfront Park for views of Lake Champlain and the Adirondack Mountains. Bike or walk the Burlington Greenway. Shop and eat at Church Street Marketplace. Treat yourself at the original Ben & Jerry’s Ice Cream Shop. Families love the ECHO, Leahy Center of Lake Champlain for hands-on science fun.

Tip: Consider staying at a local bed and breakfast or hotel. Order a travel guide and subscribe to Vermont tourism newsletters for updates. Book your trip with Milne Travel for better rates.

You will find so much to love in Middlebury.

• Middlebury ranks high on travel lists for its outdoor fun, like the Trail Around Middlebury and local marathons.

• You can explore art at the college museum and taste local drinks.
  Plan ahead to make the most of your Middlebury adventure!

FAQ

What can you do in middlebury if it rains?

You can visit the Henry Sheldon Museum, browse local shops, or catch a movie at Middlebury Marquis. Indoor activities keep you entertained.

What is the best way to explore middlebury’s downtown?

You can walk along Main Street. Stop at local cafés, shops, and galleries. The area is compact, so you see everything easily.

What food should you try in middlebury?

You should taste Vermont cheese, maple sausage, and fresh brioche buns. Visit the Middlebury Tasting Trail for local drinks and flavors.