Feel the rush as you explore Middlebury Scavenger Hunt and Middlebury College Scavenger Hunt alongside iconic landmarks and tucked-away treasures—from colorful murals to lively plazas.
Gather your group for trivia quests, bold photo dares, and wild challenges that rack up points in our sleek app—compare scores and celebrate victories together for nonstop fun!
Top Outdoor Activities In Middlebury, Vermont
Step into Middlebury, Vermont, where Otter Creek sparkles beneath the Green Mountains and adventure calls from every corner. Whether you are a first-time visitor or a local seeking fresh excitement, our outdoor activities offer the ultimate way to view Middlebury in all it's charm. From historic New England streets to vibrant college town energy, there is something for everyone. Experience the must-see sights and hidden gems that make this Addison County jewel unforgettable.
Adventurers exploring in Middlebury!
Outdoor Experiences in Middlebury, Vermont
Get ready for an unforgettable journey with our expertly curated list of outdoor activities in Middlebury! Each activity is designed to immerse you in the city’s unique vibe, blending history, art, and pure fun. Whether you are sightseeing along Marble Valley Stop or exploring Robert Frost Country, these experiences promise laughter and discovery at every turn. Embrace your adventurous side and dive into memorable moments crafted by local experts.
Top Rated
5.0 (18 reviews)
Middlebury scavenger hunt
Downtown, Middlebury, Vermont
Deere in Middlebury, venture on a thrilling scavenger hunt through downtown‘s historic...
5.0 (20 reviews)
The Midd-Quest Challenge
Middlebury College, Middlebury, Vermont
Experience a self-guided Middlebury College tour with an app-led scavenger hunt packed...
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Shelburne‘s Treasure Trot Scavenger Hunt
Downtown, Shelburne, Vermont
Join us for a wild adventure exploring the heart of Shelburne, Vermont's downtown...
27.1 mi away
5.0 (17 reviews)
Norwich University Hunt
Norwich University, Barre, Vermont
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29.4 mi away
5.0 (15 reviews)
Rutland Riddles & Revels Scavenger Hunt
Downtown, Rutland, Vermont
Deer you go! Rutland‘s hidden gems await in our downtown scavenger hunt. Discover...
An Epic Middlebury, Vermont experience
How Our Middlebury, Vermont Outdoor Activities Work
Our expert team has researched over 3,050 cities—including 50+ locations throughout the Northeast—to ensure each outdoor activity delivers authentic local flavor mixed with playful challenges tailored just for you.
During every experience in Middlebury, your team explores on foot: answering trivia at historical sites, snapping creative photos by public art installations, and solving clever puzzles at must-see landmarks—all tracked through our award-winning app so you can compare scores citywide.
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Top Outdoor Attractions In Middlebury
Middlebury’s top attractions come alive when explored through our dynamic outdoor activities. Picture yourself navigating the scenic trails near Middlebury Falls Views or unraveling clues among the storied halls of Middlebury College. Marvel at public art installations, snap photos by Otter Creek’s rushing waters, and soak up Vermont’s vibrant culture on foot. Each stop reveals new facets of this historic New England spot—perfect for families, friends, or solo explorers eager for something different. Click on each location to see related activities.
1
Addison County Courthouse
Explore the Addison County Landmark, a must-see for outdoor enthusiasts. Marvel at it's Queen Anne details and enjoy a leisurely stroll near Otter Creek Oasis. Perfect for a day trip in Middlebury.
2
Middlebury Civil War Memorial
Visit the Middlebury Tribute Plaque, an outdoor activity that honors local valor. Enjoy the peaceful surroundings and listen to Otter Creek's gentle rush nearby.
3
John Deere's Blacksmith Shop
Step into history at John Deere's Forge, where American ingenuity began. This outdoor site invites you to imagine the clang of hammers in Vermont's Heartland.
4
Civil War Cannon Plaque
The Civil War Cannon Plaque is a must-see for history buffs. Experience the legacy of the Green Mountain Gateway as you explore Middlebury's vibrant streets.
5
Marble Works Memorial Bridge
Stroll across this historic bridge, an outdoor activity filled with scenic charm in Vermont’s Heartland. Discover riddle clues near plaques and local art.
6
Emma Willard Memorial
Celebrate progress at Emma Willard Memorial, an inspiring outdoor activity in Vermont’s Cultural Crossroads. Perfect for teamwork and thoughtful reflection.
7
Samuel Miller's House
Test your knowledge at this historic landmark, where academic dreams began. Enjoy an engaging outdoor activity uncovering Middlebury’s academic legacy.
8
Middlebury War Memorial
Honor Middlebury’s bravest at this city center landmark. Reflect on community pride while enjoying an engaging outdoor activity with friends or family.
9
Middlebury Falls
Step outside and explore Middlebury's Vermont charm hub, where Otter Creek meets lively street art. Locals whisper about the hidden marble carvings tucked along the Green Mountain Gateway.
10
Davis Family Library
Wander through this Addison County jewel, where outdoor things to do abound. The breeze carries hints of craft beer from nearby patios, and you might spot a dragon sculpture only locals know.
11
Painter Hall
Enjoy Middlebury attractions with a stroll past historic New England spots. Locals say the best sunset colors reflect off Otter Creek right here—bring your camera for a memorable moment.
12
Mahaney Arts Center
Outdoor activities shine at this Vermont charm hub, where you can listen for the distant rush of Middlebury Falls. Look closely—some stones here are marked with old marbleworker initials.
13
Virtue Field House
This Addison County jewel invites you to soak up fresh air and watch college town life unfold. Locals love finding wildflowers tucked beside historic walls—see how many you can spot on your walk.
See our Top Outdoor Activities By Neighborhood
From Dragonheart Castle’s legendary grounds to bustling downtown corners filled with live music and craft beer spots, each neighborhood offers it's own flavor of adventure through our outdoor activities. For those wondering what to do in Middlebury next—click on these neighborhoods to see the related activity.
29.4 mi away
5.0 (1 reviews)
Downtown
Downtown, Middlebury, Vermont
Downtown Middlebury offers a captivating blend of history and charm, making it a top attraction. Stroll through landmarks like the Addison County Courthouse and Samuel...
29.4 mi away
5.0 (1 reviews)
Middlebury College
Middlebury College, Middlebury, Vermont
Explore Middlebury College, where Otter Creek meets campus energy. From the John Deere Blacksmith Shop to Middlebury Falls views, this Addison County jewel offers...
12,000+ Reviews For our Hunts
See what people say about our outdoor activities in Middlebury
Our happy customers rave about their experiences exploring Outdoor Activities in Middlebury! With glowing five-star reviews like 'A fantastic way to discover hidden gems,' it is no wonder locals and visitors alike keep coming back for more. Join hundreds who have made memories with us—your next adventure awaits!
We really enjoyed our time at John Deere's Blacksmith Shop. It was an informative and entertaining thing to do in Middlebury!
William C.
A great way to explore the downtown neighborhood! I appreciated how interactive and engaging this tour was for our group.
Sophia L.
Such a fun thing to do while visiting! The Middlebury Civil War Memorial was an eye-opener, making history come alive.
James H.
I loved this unique experience in Middlebury. The walking tour allowed us to see iconic landmarks we usually overlook.
Laura M.
FAQs.
LOCAL INSIGHTS
Fun Middlebury Facts and Hidden Gems
Middlebury was founded at a strategic crossing over Otter Creek during Vermont's early days as an independent republic—a true Green Mountain Gateway with stories woven into every street.
Robert Frost once called this area home; his poetic spirit still lingers among marble bridges and leafy campus paths. You might even spot a dragon motif nod
Robert Frost once called this area home; his poetic spirit still lingers among marble bridges and leafy campus paths. You might even spot a dragon motif nod
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