12 Fun & Best Things to Do in Middlebury, Vermont

Middlebury is a quaint little town on the northwestern edge of Vermont. With just over 7,000 residents in 2020, Middlebury is the 9th largest city in Vermont. It’s said that Middlebury got its name because of its position halfway between New Haven and Salisbury.

This small New England town received its charter in November of 1761, along with three other cities; Salisbury, New Haven, and Cornwall. Middlebury College was founded in 1800, and by 1830 Middlebury was the second largest town in Vermont.

Middlebury is the definition of a picturesque northeastern town with a white-steepled church, beautiful Otter Creek, and a typical Main Street with small shops and galleries. One of the most picturesque drives in Vermont is the Middlebury Gap, also known as Route 125, which traverses the spine of the Green Mountains. The Middlebury Gap is a 16-mile winding road that runs through Middlebury, Hancock, and Ripton.

Tourists come to Middlebury for relaxation and recreational activities to enjoy amid scenic spots. Visitors can hike or bike on one of the many hiking trails or golf with the Adirondack and Green Mountains as beautiful scenery. In addition, the lakes and streams provide endless opportunities for fishing, boating, and other water activities.

Visitors passionate about literature will enjoy Middlebury, where Robert Frost lived, and can even head to the Robert Frost Interpretive Trail for inspiration. Middlebury also has plenty of outlets for relaxation, including local restaurants, history museums, and the Middlebury Tasting Trail.

TL;DR

If you’re wondering what to do in Middlebury, Vermont, these ideas should get you started:

• Most significant landmark – Henry Sheldon Museum
• Best park – Otter View Park
• Best free activity – Pulp Mill Covered Bridge
• Best activity for kids – UVM Morgan Horse Farm
• Best activity for adults -Middlebury Tasting Trail
• Best food – Jessica’s Restaurant
• Best nightlife – Two Brothers Tavern
• Best all-around accommodation – Swift House Inn

Fun & Best Things to do in Middlebury, Vermont

1. UVM Morgan Horse Farm

Address: 74 Battell Dr, Weybridge, VT 05753

 The UVM Morgan Horse Farm is consistently ranked as one of the top things to do near Middlebury, Vermont. For those unfamiliar, the Morgan horse is Vermont’s official state animal. This working farm has more than 40 Morgans and is open to the public between May and October. 

To enjoy Morgan Horse Farm, you don’t have to be a self-declared horse lover. Many people that visit the UVM Morgan Horse Farm have never ridden a horse before but still enjoy the history and beauty of the majestic horses. 

The name “Morgan Horse” comes from the breed’s first horse owner, Justin Morgan. His horse, “Figure,” was born in 1789 and was a fast and strong horse. Figure fathered other horses that were also fast and strong; before long, they were known as Morgan horses. 

Morgan horses were used for military campaigns during the Civil War because of their hardiness. In the early 20th Century, the United States government adopted them as the official military horse by establishing the U.S. Government Horse Farm in Weybridge, Vermont.

You can visit the farm to learn more about Vermont’s famous horses and see the majestic horses in person. Whether or not you’re an equestrian, this is one of the best places to visit in Middlebury, Vermont. Both children and adults alike will enjoy this attraction just a short drive away.

See Related: Fun & Best Things to Do in Stowe, Vermont

2. Henry Sheldon Museum

Address: 1 Park St, Middlebury, VT 05753

Opened in 1884, the Henry Sheldon Museum is the oldest community-based museum in the United States. The museum’s collection is in the original Judd-Harris House, built in 1829 by local quarry owners. It’s said that Henry Sheldon was once a boarder at the Judd-Harris House and began to fill the home with paintings, objects, and artifacts showcasing the history of Addison County.

In 1882, Sheldon purchased the Judd-Harris House and founded the Sheldon Art and Archaeological Museum and Historical Society. The three-story brick house is a tribute to the original owner’s expertise in the marble industry, with beautiful marble columns and black marble fireplaces. The house, now the Henry Sheldon Museum, continues to be a prominent sight in the center of Middlebury.

The museum offers fascinating history and art exhibits for all those seeking to learn about Vermont’s history. In addition, the state’s premier archival collections are on-site for genealogists, scholars, and the community. Want to learn more about Vermont’s history? The Henry Sheldon Museum is well worth the trip.

3. Otter View Park

Address: Weybridge St, Middlebury, VT 05753

 Otter View Park is a fantastic place for kids and adults, with a 0.6-mile trail for all skill levels. In addition, the course features a boardwalk that connects to Otter Creek River and is perfect for birdwatching, dog-walking, and hiking. 

The park is excellent for families because it has a picnic area and a short hiking trail. It also has beautiful views of the surrounding mountains and the Otter River. Otter View Park also allows visitors to see river otters (how the park got its name). Visitors can also fish, bird watch, find wildflowers, see butterflies, and enjoy nature. 

The park is the perfect habitat for many birds and a migratory feeding and resting area for other types of birds. So, if you’re a fan of birdwatching, you may find a rare species here! Exploring Middlebury at Otter View Park is a fun time for all. It’s open from dawn to dusk and has no admission fee. The Trail and Ecological Guide is very helpful before heading to the park.

See Related: Fun & Best Things to Do in Burlington, Vermont

4. Jessica’s Restaurant

Address: 25 Stewart Ln, Middlebury, VT 05753

Whether staying at the Swift Inn or not, a visit to Jessica’s Restaurant should be on your vacation to-do list. Located just two blocks from downtown, Jessica’s is convenient to most local attractions.

Although the restaurant is in a home built in 1814, the atmosphere is casual enough for a family dinner or a nice dinner for two. The restaurant has indoor and outdoor seating with beautiful views of the sunset.  

There is a daily breakfast buffet featuring an egg dish, freshly baked pastries, Vermont maple Sausage, and a parfait bar. If you’re a guest at the Swift Inn, the breakfast buffet is complimentary; however, guests staying elsewhere pay $20 per person for the breakfast buffet. 

In addition to fantastic food, Jessica’s Restaurant has been recognized by Wine Spectator for the Best of Award of Excellence. With less than 1,200 restaurants worldwide with this award, Jessica’s Restaurant is proud to receive this distinction. They have an extensive selection of wines for all tastes. 

If you want to stay at the Swift House Inn, there are 20 unique guest rooms across the three-building inn. Amenities include a seasonal fireplace, a private outdoor patio or deck, and a bathtub. The highly-rated and conveniently-located SwiftInn House is a Vermont favorite. 

 5. Pulp Mill Covered Bridge

Address: Weybridge, VT 05753

Listed on the National Register of Historic Places, the Pulp Mill Covered Bridge crosses Otter Creek in Middlebury. Although it is known as the oldest covered bridge in Vermont, the exact date of construction is in question. While a sign on the Pulp Mill Covered Bridge states that it was built between 1808 and 1820, a bridge expert believes it was constructed around 1850. 

The bridge is unique for a few reasons:

• It is one of only seven two-lane covered bridges in the U.S.
• It is one of only two covered two-lane bridges in Vermont 
• It’s the only covered two-lane bridge still carrying regular traffic. 

Covering bridges during the 19th Century was to protect the trusses and decks from rain and snow. The decks and trusses could decay and rot without the cover from poor weather conditions. 

If you want to drive through a piece of Vermont’s history, head to the Pulp Mill Covered Bridge, 199 feet long and 22.5 feet wide. Take this opportunity to try Otter Creek Brewing Company, less than half a mile from the bridge.

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 6. Middlebury Tasting Trail

Address: (starting from Lincoln Peak Vineyard) 142 River Rd. New Haven, VT  05472

The Middlebury Tasting Trail includes seven local vineyards, distilleries, and breweries within a few miles. To complete the entire tasting trail, you can visit in the following order from north to south:

Start at Lincoln Peak Vineyard (142 River Rd. New Haven, VT  05472), where they are known for their Marquette and Farnsworth grapes. Then head south to Woodchuck Hard Cider (1321 Exchange St. Middlebury, VT  05753) for cider tastings and a self-guided tour.

If you want to try unique spirits, head to Appalachian Gap Distillery (88 Mainelli Rd. Middlebury, VT 05753), where they have coffee-infused bourbon and a malt whiskey redolent of hops.

If you’re looking for munchies and cold beer, Otter Creek Brewery (793 Exchange St. Middlebury, VT  05753) is the place to go. If you feel too full of drinking any more beer, get a growler or two to take home at Drop-In Brewing (610 Route 7 South Middlebury, VT  05753).

The last two stops on the trail include Windfall Orchard (1491 Rt 30 Cornwall, VT 05753) and Golden Rule Mead (8 Elm Street Middlebury, VT 05753), where you can try small batch cider products and locally-sourced mead. This tasting trail is definitely one of the best things to do in Middlebury for adults.

See Related: Best Wineries in Temecula to Visit | Top Vineyard Tours

7. Middlebury College Museum of Art

Address: 72 Porter Field Rd, Middlebury, VT 05753

The Middlebury College Museum of Art is a vital educational component of Middlebury College. The museum is a must-see destination for history lovers with thousands of artifacts ranging from 19th Century sculptures, Asian art, and contemporary prints. 

The art museum produces 6–8 exhibits yearly in addition to their permanent collection display of works. Temporary exhibitions are usually borrowed from institutions specializing in traveling shows or other museum collections. Not only does the museum maintain the artifacts within the building, but it also maintains 25 sculptures located in various places on Middlebury’s campus. 

An upcoming exhibit includes scenes from Johannesburg and Lagos. These two African cities have experienced tremendous growth over recent years, and the street scenes showcase the complex stories of the people. Art includes tales of desperation, hope, migration, labor, and imagination. This art museum is one of the best free things to do in Middlebury, Vermont.

See Related: ​​Best Museums in Europe to Visit

8. Green Mountain National Forest

Address: 231 N Main St, Rutland, VT 05701

The Green Mountain National Forest is a short 50-minute drive from Middlebury and is the perfect place for all-season recreation. You can enjoy hiking, mountain biking, camping, fishing, and hunting during the spring, summer, and fall, and cross-country skiing and snowshoeing in the winter. 

Not only is the national forest a fantastic place for outdoor recreation, but it also contains more than 2,000 historic sites. Some of the most notable areas include Native American archeological sites, colonial-era farmsteads, and tools from the industrial period. 

The 100-mile “West-Central Mountains and the Appalachian Gap Loop” goes through the national forest, around Lake Dunmore, and through nearby towns such as Ripton, Hancock, and Salisbury. If you’re lucky, you may even be able to spot a moose during your visit. Without a doubt, this is one of the best things to do in Middlebury, Vermont, because there’s something for everyone to enjoy!

The Forest Service manages reservations, camping, and cabin information for the park. Don’t want to camp? Then, head back to Middlebury and stay in an excellent Victorian hotel. 

See Related: Fun & Best Things to Do in Dorset, Vermont

9. Town Hall Theater

Address:  68 S Pleasant St, Middlebury, VT 05753

The beginning of Town Hall Theater’s history dates back to 1883, when residents and city leaders wanted to establish a social and cultural center in Middlebury. After looking at eight locations across the town, they settled on a prominent site overlooking the town green for the new Town Hall. The architecture firm that designed the building would eventually develop the new Addison County Courthouse, the Beckwith Block, Shard Villa, and many other local buildings.

The new Town Hall was complete in 1884 and opened with a Masquerade Ball. The main floor of the building included a 600-seat theater with a balcony, and the exterior had a large tower. The building has a long history, from vaudeville shows, religious services, lectures, readings, minstrel shows, high school graduations, and fairs to dance recitals and dog and pony shows.

The restored theater reopened with great fanfare on July 26, 2008. Today, Town Hall Theater (also known as THT) features live music, theater performances, opera concerts, film screenings, and more. Make sure to see a show when you visit- there’s something for everyone! After the show, head to the Two Brothers Tavern for pub grub and a frosty beverage.

See Related: Most Beautiful Fairy Tale Towns Around the World

10. Vermont Folklife Center

Address: 88 Main Street Middlebury, VT 05753

 The Vermont Folklife Center is an educational organization aiming to teach visitors about Vermont’s diverse communities. The center, founded in 1984, uses interviews, observation, and participation, to teach museumgoers about the state’s culture and social fabric. 

The fieldwork is ongoing, with the museum’s folklorists conducting at least 100 interviews annually. The museum can use these firsthand accounts for website audio, radio broadcasts, documentary exhibits, or educational programs. 

While 100 interviews per year may not seem like much, the Vermont Folklife Center (VFC) has more than 5,000 interviews stored in its climate-controlled archive house. Not only does the center have archived interviews, but also field notes, transcripts, musical recordings, memoirs, and photographs. If you want to explore Vermont’s history, the Folklife Center is one of the best historical things to do in Middlebury.

See Related: Best Museums for Kids in Washington D.C.

11. Seymour Street

Address: Seymour Street Middlebury, VT

Seymour Street begins at the old Pulp Mill Bridge on the northwest side of town over Otter Creek and deadends just past Main Street at S. Pleasant Drive. This beautiful and iconic street is home to much of the town’s history, with the former railroad passenger depot, the Dudley-Painter House, and the Congregational Church still in existence.

The Dudley-Painter house was initially built in the late 18th Century at S. Pleasant Street and Merchants Row, but then it moved to its current location on Seymour Street at the beginning of the 19th Century. At 7 Seymour Street, the small white house is now an office suite for local businesses. But unfortunately, most people driving by don’t know it’s the oldest house in town.

In addition to the railroad depot and the Dudley-Painter House, the Congregational Church was built in the early 19th Century. This beautiful church was one of the finest Federal-style churches in the northeast. Seymour Street captures the architecture and history of the 19th Century, with modern additions such as the Middlebury Fire Department, the National Bank of Middlebury, and the Amtrak Station.

12. Hike, Bike, or Trek the Middlebury Trails

Address: various trailheads

Middlebury has endless hiking and biking trails for the outdoor enthusiast, from short paved trails to long, challenging, steep trails. There are so many fantastic trails with views of the mountains, lakes, and river gorges that it might be hard to decide which one to start with. Circling the city lies the 19-mile Trail Around Middlebury (TAM), which is an easy choice if you don’t want to drive to a nearby trailhead. 

A short 30-minute drive away is Texas Falls Recreation Area, a beautiful park next to Lake Champlain and the Scenic Route 100 Byway. There are two different trails with gorgeous views of cascading waterfalls along scenic gorges.

The easy 1.2-mile Robert Frost Interpretive Trail is a 20-minute drive from Middlebury in Ripton. The trail combines inspiring bits of Robert Frost’s literature with beautiful scenery. Delicious blueberries and huckleberries grow in an open field at the trail’s end. You can also stay at the Robert Frost Mountain Cabins.

With over 70 miles of trails, the Moosalamoo National Recreation Area has something for everyone. The Silver Lake Area includes routes between 0.6 and 8.8 miles, with gorgeous upland hills, creeks, and valleys. If you’re looking for a multi-day adventure, look for a path that connects to the Long Trail to allow for a more extended expedition. 

Other nearby hikes include Bristol Ledges and Snake Mountain Wildlife Management Area. The Bristol Ledges Trail is about 3 miles round trip, with ledges at the top facing out towards downtown Bristol. It’s a fantastic place for watching the sunset. 

The 2.25-mile trail at Snake Mountain Wildlife Management Area is relatively flat initially but gains roughly 1,000 feet of elevation. You can see the lake and the beautiful Adirondack Mountains at the peak. In addition, several state parks in the surrounding area have incredible trails. You will be met with astounding beauty wherever you go, regardless of the season.

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