Experience a rush exploring Middlebury Scavenger Hunt and Middlebury College Scavenger Hunt alongside iconic landmarks and hidden gems—discover vibrant street art one moment, then wander historic plazas or leafy college quads the next.
Gather your crew for trivia quests, bold photo dares, and wild challenges that earn points through our sleek app—compare scores instantly and celebrate victories together after every round.
Top Outdoor Activities In Middlebury, Vermont
Step into the vibrant heart of Middlebury, where Otter Creek sparkles and Green Mountain Gateway beckons adventurers. Whether you are a first-time visitor or a local seeking fresh views, our outdoor activities promise to transform your day trip into an unforgettable journey. From must-see landmarks to hidden corners bursting with Vermont charm, there is something for everyone. Make every moment count as you view Middlebury in a brand new way.
Adventurers exploring in Middlebury!
Outdoor Experiences in Middlebury, Vermont
Get ready for an expertly curated lineup of outdoor activities in Middlebury that blend excitement, discovery, and pure fun. Each adventure is designed to immerse you in the unique spirit of this Vermont gem—think creative challenges, surprising sights, and plenty of laughter along the way. Our activities offer more than sightseeing; they invite you to connect with local culture and history while making lasting memories. Dive in and discover why these experiences are among the top things to do when visiting Middlebury.
Top Rated
5.0 (275 reviews)
Middlebury scavenger hunt
Downtown, Middlebury, Vermont
Deere in Middlebury, venture on a thrilling scavenger hunt through downtown‘s historic...
5.0 (68 reviews)
The Midd-Quest Challenge
Middlebury College, Middlebury, Vermont
Experience a self-guided Middlebury College tour with an app-led scavenger hunt packed...
5.0 (64 reviews)
Middlebury College Scavenger Hunt
Middlebury College, Middlebury, Vermont
Experience a self-guided Middlebury College tour with an app-led scavenger hunt packed...
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An Epic Middlebury, Vermont experience
How Our Middlebury, Vermont Outdoor Activities Work
Our expert team researches cities worldwide—including over 3,050 destinations—to design unforgettable outdoor adventures tailored just for you! In Northeast cities alone we offer 50+ unique experiences blending history with creative challenges.
During each activity your group explores on foot: answer trivia at historical markers, tackle photo challenges at public art installations, solve puzzles by local landmarks—all tracked through our award-winning app so you can earn points and compare scores citywide.
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Top Outdoor Attractions In Middlebury
Middlebury attractions dazzle with their blend of historic beauty and modern flair—picture strolling past marble bridges, lively art galleries, and the iconic Middlebury College campus. Outdoor activities here invite you to interact with must-see spots like bustling Main Street or tranquil riverside trails while uncovering stories behind each landmark. Feel the pulse of live music venues or snap photos at colorful murals as part of your adventure. 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.
14
Otter Creek Falls
Step into Robert Frost Country and discover outdoor gems where Otter Creek flows. Locals say the best Middlebury Falls views are found along the Marble Valley Stop, especially at sunset.
15
John Deere Inventor
Wander the Green Mountain Gateway and spot dragon sculptures tucked away by locals. This historic New England spot offers fresh air and a sense of discovery for those exploring outdoor activities.
16
Middlebury College Bookstore
Enjoy the Vermont charm hub with riverside trails and leafy escapes. Locals recommend listening for the rush of Otter Creek as you stroll—an Addison County secret worth experiencing outdoors.
17
Davis Family Library
Explore Robert Frost Country with a walk past historic bridges and hidden gardens. Outdoor enthusiasts love this spot for it's peaceful vibe and occasional glimpses of local wildlife.
18
Painter Hall
Discover Dragonheart Castle's quirky exterior—rumor has it, a local artist added secret carvings only visible on sunny days. It is a fun outdoor stop when exploring Middlebury's creative side.
19
Mahaney Arts Center
Marvel at sweeping Middlebury Falls views from this Marble Valley stop. The sound of rushing water makes it a top pick for outdoor activities—locals bring picnics here on warm afternoons.
See our Top Outdoor Activities By Neighborhood
From College Town energy to Marble Valley's scenic streets, each neighborhood offers it's own flavor of outdoor fun in Middlebury. These areas are packed with unique experiences waiting for you—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...
29.4 mi away
5.0 (1 reviews)
Middlebury College
Middlebury College, Middlebury, Vermont
Discover why Middlebury College is a top thing to do in Middlebury. From the iconic Davis Family Library to the scenic Otter Creek Falls, this Addison County Jewel...
12,000+ Reviews For our Hunts
See what people say about our outdoor activities in Middlebury
Locals and visitors rave about our outdoor activities in Middlebury! Guests love discovering city secrets together—one happy customer said it was 'the highlight of our weekend.' With glowing five-star ratings across the board, these adventures have earned their place as recommended outdoor activities for all ages.
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 began as a small settlement near Otter Creek Falls back in 1761—a perfect spot for mills powered by rushing water. The town quickly became known as Vermont's Marble Valley Stop thanks to it's rich stone quarries.
Today, locals cherish traditions from Robert Frost readings on campus lawns to annual festivals celebrating art and live
Today, locals cherish traditions from Robert Frost readings on campus lawns to annual festivals celebrating art and live
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