13 Most Fun Things To Do In Middlebury, VT

Middlebury is a charming town within the scenic embrace of Vermont. The city beckons visitors with its rich history, natural wonders, and cultural treasures. Here, we explore some interesting facts and the allure that makes Middlebury a popular destination.

The city was founded in 1761 and boasts a storied past. It’s home to Middlebury College, one of the oldest liberal arts colleges in the country, established in 1800. The town’s historical architecture, including the picturesque covered bridges, is a testament to its enduring legacy.

Middlebury attracts over 100,000 visitors annually. Its appeal lies in the blend of cultural attractions, outdoor adventures, and welcoming community. The Robert Frost Interpretive Trail and the Middlebury College Museum of Art offer unique cultural experiences.

Surrounded by the Green Mountains, Middlebury is an outdoor enthusiast’s paradise. Hiking, skiing, and kayaking opportunities abound. The serene Otter Creek Falls and the scenic Lake Dunmore are just a stone’s throw away.

Middlebury experiences four distinct seasons. Summers are warm and pleasant, while fall explodes with vibrant foliage. Winters are snowy, perfect for winter sports, and spring brings renewed greenery.

The best time to visit Middlebury depends on your interests. Summer and early fall are ideal for outdoor adventures and festivals. Autumn is a visual spectacle as the foliage turns vibrant shades. Winter offers cozy retreats, and spring brings forth budding beauty.

Middlebury, VT, is a place where history meets nature, creating a captivating destination for all who seek a harmonious blend of culture and outdoor exploration. Check out the 13 most fun things to do in Middlebury, VT.

1) Explore the Robert Frost Interpretive Trail

The Robert Frost Interpretive Trail celebrates the famous poet Robert Frost and his love for nature. It’s a serene place where you can walk among trees and read parts of Frost’s poems along the way.

Explore the Robert Frost Interpretive Trail
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This trail was created in 2002 to honor Robert Frost, who lived in Ripton for over 20 years. It’s a place where his poems come alive amidst the woods.

The trail is about a half-mile long, and it’s not too hard to walk. You’ll find plaques with verses from Frost’s poems along the way. These words remind you of the beauty of the natural world.

You can see the cabin where Frost wrote many of his famous poems, like “Stopping by Woods on a Snowy Evening.” Frost found inspiration in the forests and fields of Vermont.

It’s a lovely spot for anyone who enjoys poetry or simply wants a peaceful walk in the woods. The best part? It’s free, so you can enjoy nature’s beauty and Robert Frost’s words without spending a dime.


Middlebury, VT 05753, United States

2) Visit Middlebury College Museum of Art

The Middlebury College Museum of Art is a place to see and learn about different kinds of art. This museum has been around for a long time, since 1968. It’s in the Mahaney Arts Center, which is part of Middlebury College.

Visit Middlebury College Museum of Art
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Inside, there are lots of paintings, sculptures, and other art pieces from different times and places. You can see art from Europe, America, and other parts of the world.

The museum is free for everyone, so you don’t need to pay to go in and look at the art. It’s a great place to learn and have fun. If you like art and history, this museum is a cool place to visit. You can see beautiful and thought-provoking art without spending any money. It’s a win-win


72 Porter Field Rd, Middlebury, VT 05753, United States

3) Stroll Along the Otter Creek Falls

Otter Creek Falls, located in Middlebury, Vermont, is a scenic waterfall that has a rich history and captivating natural beauty. These falls have been an important part of Middlebury for a long time. They powered mills and factories in the past, helping the town grow.

Stroll Along the Otter Creek Falls
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The falls are about 37 feet high and are known for their rocky surroundings and the sound of rushing water. Otter Creek Falls is a popular spot for both locals and visitors. You can hike or walk around the area, have picnics, or just enjoy the beautiful views.

The falls look stunning in all seasons, whether it’s the vibrant colors of fall foliage or the icy beauty of winter. If you love the waterfalls, or just want a peaceful place to relax, Otter Creek Falls is a great destination. It’s a spot where history, nature, and serenity come together in a beautiful way.


Middlebury, VT 05753, United States

4) Town Hall Theater

The Town Hall Theater is a historic and cultural gem known for its rich history and diverse performances. The theater has been around since the late 19th century and has seen many changes over the years. It was once a place for town meetings and community events.

Town Hall Theater
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In the 2000s, it underwent a major renovation to become the vibrant cultural hub it is today. The theater hosts a wide range of events, from live music performances and theater productions to dance shows and films.

It’s known for its intimate setting, where every seat feels close to the stage, creating a special connection between the performers and the audience. Many famous artists and musicians have graced the Town Hall Theater’s stage over the years.

Visit: If you enjoy live performances and want to experience the charm of a historic theater, the Town Hall Theater is a must-visit. It’s a place where history and the arts come together to create memorable experiences for all.


68 S Pleasant St, Middlebury, VT 05753, United States

5) Henry Sheldon Museum of Vermont History

The Henry Sheldon Museum of Vermont History is located in Middlebury, Vermont. It is a place where you can explore the state’s rich history through fascinating exhibits and artifacts.

Henry Sheldon Museum of Vermont History
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The museum was founded in 1882 and is one of the oldest community museums in the United States. It’s named after Henry Sheldon, a local historian. Inside, you’ll find a wide variety of things, like old photographs, furniture, clothes, and tools. These items tell the story of Vermont and its people.

The museum hosts different exhibitions throughout the year, so there’s always something new to see and learn. You can see interesting things, like an 18th-century stagecoach and a portrait gallery of notable Vermonters.

The museum building itself is a piece of history, dating back to the early 1800s. If you’re curious about Vermont’s past or want to know its history, visiting Henry Sheldon Museum might be the best thing for you.


1 Park St, Middlebury, VT 05753, United States

6) Experience the Vermont Folklife Center

The Vermont Folklife Center is a place dedicated to preserving and celebrating the traditions and stories of Vermonters. The center was founded in 1984, aiming to document and share the rich cultural heritage of Vermont through oral histories, exhibits, and educational programs.

Experience the Vermont Folklife Center
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Its mission is to make sure the voices and traditions of everyday Vermonters are heard and appreciated. The center hosts interactive exhibits that showcase the stories, crafts, and traditions of Vermonters. These exhibits often change, so there’s always something new to see.

One of the unique things about the center is its vast collection of oral histories, where people share their life experiences and stories in their own words. The center also supports traditional Vermont folk arts, like storytelling, music, and craft-making.

If you’re interested in the stories and traditions that make Vermont special, the Vermont Folklife Center is a place to explore. It’s a living museum of Vermont’s cultural heritage, celebrating the everyday people who make this state unique.


88 Main St, Middlebury, VT 05753, United States

7) Drop-In Brewing Company

The Drop-In Brewing Company is a craft brewery known for its history and innovation. The brewery was founded in 2012 by two friends, Steve Parkes and Christine McKeever, who had a passion for brewing unique and flavorful beers.

Drop-In Brewing Company
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It’s housed in a historic building that was once a coffee roasting company, adding a touch of character to the brewing process. Drop-In Brewing Company is dedicated to making high-quality, small-batch craft beers. They experiment with different ingredients and styles to create diverse brews.

The brewery often hosts events and gatherings, creating a sense of community among beer enthusiasts. Drop-In Brewing Company is committed to sustainability and uses renewable energy to power its brewing operations.

They’ve brewed over 50 beers since they started, each with unique flavors and character, If you’re a beer lover or want to explore the world of craft brewing, Drop-In Brewing Company is a great place to visit. 

You can taste their innovative beers and enjoy the welcoming atmosphere of their brewery. It’s where history meets a passion for brewing.


610 US-7, Middlebury, VT 05753, United States

8) Werner Tree Farm

Werner Tree Farm, nestled in Middlebury, Vermont, is a haven for those seeking a unique and festive holiday experience. This family-owned tree farm has been a part of Middlebury’s holiday traditions for decades, offering visitors the chance to select and cut their own Christmas trees.

Werner Tree Farm
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The farm features a variety of evergreen trees, from classic Balsam and Fraser Firs to vibrant Blue Spruces, ensuring a perfect fit for any holiday décor. 

One of the farm’s main attractions is the opportunity for families to explore the fields and select their own tree. It’s a cherished tradition that creates lasting memories.

The farm goes all out during the holiday season, with decorations, festive music, and hot cocoa to warm your spirits. Werner Tree Farm has been featured in national publications for its dedication to sustainable and eco-friendly tree farming practices.

Whether you’re starting a new holiday tradition or continuing a long-standing one, Werner Tree Farm offers a magical experience that captures the spirit of the season. It’s a place where the smell of evergreen and the joy of the holidays come together in perfect harmony.


429 Painter Rd, Middlebury, VT 05753, United States

9) Discover the Danforth Pewter Workshop

The Danforth Pewter Workshop is a fascinating place known for its rich history and intricate pewter craftsmanship. The workshop was founded in 1975 by Fred and Judi Danforth, who were passionate about creating beautiful pewter products using traditional methods.

Discover the Danforth Pewter Workshop
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At Danforth Pewter, skilled artisans create pewter pieces by hand, using time-honored techniques. Each piece is a work of art.  Visitors can take guided tours to see the artisans at work, turning molten pewter into intricate designs. It’s a chance to witness the artistry up close.

The workshop is committed to eco-friendly practices, using recycled materials and minimizing waste. They offer a wide range of pewter products, from jewelry to home décor, with intricate designs that reflect the beauty of Vermont.

If you appreciate handmade craftsmanship and want to take home a piece of Vermont’s artistic heritage, a visit to the Danforth Pewter Workshop is a must. It’s a place where history and artistry come together to create timeless treasures.


52 Seymour St, Middlebury, VT 05753, United States

10) Cobble Hill Kennel

Cobble Hill Kennel is a beloved place for pet owners seeking top-notch care and accommodations for their furry friends. Cobble Hill Kennel has been serving the community for years, providing a safe and comfortable environment for pets. 

Cobble Hill Kennel
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The kennel is well-known for its dedicated team of professionals who are passionate about animals, ensuring that every pet receives individualized attention, from feeding preferences to medical needs.

It offers spacious outdoor play areas where dogs can run and socialize, ensuring they get the exercise and mental stimulation they need. The kennel is a favorite spot for pets during holidays or vacations, with cozy sleeping areas and plenty of love and care from the staff.

Cobble Hill Kennel has a reputation for its commitment to the well-being of pets, making it a trusted choice for pet owners in the area.

Whether it’s a short stay or an extended vacation, pet owners can have peace of mind knowing their dogs are in capable hands at Cobble Hill Kennel, where history and a love for animals come together to provide exceptional care.


Pvt, Sheldon Ln, Middlebury, VT 05753, United States

11) Ralph Myhre Golf Course

The Ralph Myhre Golf Course, located in Middlebury, Vermont, is a picturesque and historic destination for golf enthusiasts. The golf course has been welcoming golfers since 1929 and is named after Ralph Myhre, a local golfing legend. It’s one of the oldest golf courses in Vermont.

Ralph Myhre Golf Course
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The course is known for its scenic beauty, with rolling fairways, well-maintained greens, and stunning views of the Green Mountains. Golfers of all levels can enjoy the course, with practice facilities like a driving range and putting green to sharpen their skills.

One interesting fact about the course is that it’s home to the infamous “Swinging Bridge,” a bridge that sways as golfers walk across it. Ralph Myhre Golf Course is known for being affordable, making it accessible to both locals and visitors.

If you love golf or simply enjoy the outdoors, a visit to the Ralph Myhre Golf Course is a must. It’s where history, natural beauty, and the joy of golfing come together for an enjoyable experience.


317 Golf Course Rd, Middlebury, VT 05753, United States

12) Mahaney Arts Center

The Mahaney Arts Center is a vibrant cultural hub with a rich history and a commitment to the arts. The center has been a part of Middlebury College since 1992, providing a space for artistic expression and creativity. 

Mahaney Arts Center
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It houses world-class theaters, galleries, and studios, creating a welcoming environment for artists to showcase their talents. The center hosts various events, from theater productions to music concerts, dance performances, and art exhibitions, catering to various artistic interests.

Interestingly, the center’s intimate theaters connect performers and the audience, enhancing the overall experience. The center also supports educational programs, encouraging students and the community to engage with the arts.

Whether you’re an art enthusiast or simply looking to enjoy a live performance, the Mahaney Arts Center is a must-visit. It’s where history, creativity, and culture come together to enrich the lives of those who appreciate the arts.


Middlebury College, 72 Porter Field Rd, Middlebury, VT 05753, United States

13) Lincoln Peak Vineyard

Lincoln Peak Vineyard is a charming winery with a rich history and a focus on crafting exceptional wines. Established in 2002, this family-owned vineyard is set amidst the picturesque landscape of Vermont. It’s known for its commitment to producing high-quality wines.

Lincoln Peak Vineyard
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Lincoln Peak Vineyard specializes in crafting various wines, including reds, whites, and rosés, using grapes that thrive in Vermont’s climate. One interesting fact is that the vineyard is committed to sustainable farming practices, ensuring their wines reflect the purity of the Vermont terroir.

Visitors can enjoy tastings at the vineyard’s tasting room, where you can savor the unique flavors and aromas of their wines. The vineyard offers stunning views of the Green Mountains, making it a perfect spot to relax and enjoy a glass of wine.

Whether you’re a wine enthusiast or just looking for a peaceful escape, a visit to Lincoln Peak Vineyard is a delightful experience. It’s where history and a passion for winemaking come together to create a taste of Vermont in every bottle.


142 River Rd, New Haven, VT 05472, United States


Middlebury, VT, is a hidden gem that offers a blend of cultural, natural, and recreational activities. Whether you are seeking artistic inspiration, outdoor adventures, or a taste of local culture, Middlebury has it all. Plan your visit to this charming town and immerse yourself in its unique offerings.