Get swept up in the excitement as you explore Chestertown Scavenger Hunt and Washington College Scavenger Hunt alongside iconic landmarks and hidden gems—from vibrant street art to bustling plazas.
Gather your team for trivia quests, daring photo challenges, and creative tasks that rack up points in our easy-to-use app—compare scores with friends and celebrate your victories together!
Top Outdoor Activities In Chestertown, Maryland
Step into the heart of Chestertown, where Colonial Riverfront charm and waterfront heritage set the stage for unforgettable adventures. Whether you are a local or visiting Chestertown for a day trip, our outdoor activities invite you to discover must-see sights and hidden gems. Wander quaint brick streets, soak in vibrant art galleries, and experience lively corners of this historic Maryland town. Outdoor activities here offer the ultimate way to view Chestertown from a fresh perspective while making lasting memories.
Outdoor Experiences in Chestertown, Maryland
Welcome to our expertly curated collection of outdoor activities in Chestertown! Each adventure is designed to help you uncover the unique spirit of this Eastern Shore gem—perfect for sightseeing, exploring top attractions, or adding excitement to your next outing. Our experiences blend fun challenges with immersive exploration so that every participant discovers something new about Chestertown's culture and history. Get ready for an exhilarating journey through picturesque neighborhoods and iconic spots as you embark on these recommended outdoor activities.
Top Rated
5.0 (16 reviews)
Chestertown Chasers‘ Treasure Hunt Scavenger Hunt
Downtown, Chestertown
Chestertown‘s treasure ain‘t just George Washington‘s dentures! Discover hidden gems...
5.0 (14 reviews)
The Chestertown Challenge
Washington College, Chestertown
Experience a self-guided, app-led Washington College tour with trivia, photo challenges,...
An epic Chestertown, Maryland experience
How Our Chestertown, Maryland Outdoor Activities Work
Our expert team researches over 3,050 cities—including more than 50 across Southeast—to design each outdoor activity around must-see locations and secret highlights unique to every destination. You will find clear instructions, route maps tailored for walking tours, challenge quizzes inspired by local stories, plus themed routes such as college campuses or riverfronts.
During each activity in Chestertown your group explores on foot: answering trivia at historical markers near art galleries or solving puzzles beside public installations downtown. Earn points via our award-winning app—and compare scores against others enjoying similar adventures throughout town.
Top Outdoor Attractions In Chestertown
Chestertown's top attractions come alive when explored through engaging outdoor activities that reveal their true character. From the storied halls of Washington College to bustling Historic Downtown and scenic Chester River views, each location offers it's own blend of history, art, and small-town warmth. Stroll past centuries-old architecture, snap photos at colorful murals, or test your wits at local landmarks—all while soaking up live music and craft beer along the way. Click on each location to see related activities.
George Vickers
Discover the George Vickers plaque in Chestertown's historic downtown. Locals say his spirit echoes through the Blue Crab Festival. Enjoy a day trip filled with history and charm.
John Leeds Barroll
Visit the John Leeds Barroll marker, a must-see for history buffs. This spot once buzzed with newsworthy tales. Enjoy an Artsy Main Street Stroll and soak in Washington College Town vibes.
Chestertown Historic District
Explore the Chestertown Historic District, where quaint brick streets whisper stories of old. Locals hint at a house with a cannonball dent nearby—perfect for sightseeing and discovery.
Common Cause
Visit the Common Cause marker, buzzing with Revolutionary energy during May's Tea Party reenactment. Capture the spirit of Kent County's heart and enjoy this unique thing to do in Chestertown.
George Washington
Spot Washington keeping watch over Chestertown—a must-see for visitors! Rumor has it students prank his hat during graduation week. Enjoy this quirky tradition on your day trip.
Revolution on the River
Stand where townsfolk once defied Britain by dumping tea into Chester River—a Chesapeake Bay Gateway experience! Feel history's echoes on breezy days at this Eastern Shore Adventure Spot.
William Beck Nicholson statue
Enjoy Chestertown's Colonial Riverfront charm as you stroll the historic downtown. Quaint brick streets and waterfront heritage make this a must-see for outdoor explorers seeking local flavor.
Chestertown Public School Tower
Wander the Eastern Shore and soak in Chestertown's vibrant outdoor scene. Spot hidden murals or catch the Tea Party Festival hub energy—perfect for first-time visitors craving something memorable.
George Washington statue
Explore Kent County's heart by the water, where locals gather for riverside picnics and laughter echoes off the docks. Outdoor activities here offer a taste of Chestertown's waterfront heritage.
Miller Library
Step onto Chestertown's quaint brick streets for an outdoor adventure packed with history and charm. You might even spot a secret garden only locals know about—perfect for a leisurely stroll.
Daniel Z. Gibson Center for the Arts
Breathe in fresh river air while exploring Chestertown's scenic pathways. Outdoor enthusiasts love the blend of waterfront heritage and hidden gems tucked along these inviting routes.
See our Top Outdoor Activities By Neighborhood
Discover how outdoor activities can transform your experience in Chestertown's most beloved neighborhoods. Whether wandering through Kent County's Heart or immersing yourself in Chesapeake Bay Gateway vibes, these adventures capture what makes each area special—click on these neighborhoods to see the related activity.
Top Rated
5.0 (1 reviews)
Downtown
Downtown, Chestertown
Discover the must-see sights of Downtown Chestertown. With it's quaint brick streets and historic landmarks like George Washington's influence, it is a top attraction...
5.0 (1 reviews)
Washington College
Washington College, Chestertown
Washington College blends Eastern Shore charm with historic landmarks like the William Beck Nicholson statue and Daniel Z. Gibson Center for the Arts. It is a top...
See what people say about our outdoor activities in Chestertown
Our outdoor activities have earned rave reviews from families and friends seeking fun things to do in Chestertown. Five-star ratings highlight why people love discovering local attractions with us—'Best day trip ever!' echoes one happy guest. Trust our proven approach for memorable adventures every time.
Using ScavengerHunt.com made exploring downtown so enjoyable! It guided us through interesting spots we might have missed otherwise.
William L.
We had so much fun on this walking tour! It was a great way to explore downtown and learn about its rich history without feeling rushed.
Sophia H.
This experience was truly unique! I loved how interactive it was, especially getting to see John Leeds Barroll's historical significance.
James M.
I highly recommend this as a fun thing to do for tourists visiting Chestertown. The historical spots we saw were fascinating and well worth it.
Laura G.
Exploring downtown Chestertown was such a treat. The highlights of this walking tour made it one of my favorite things to do in town.
Daniel M.
The outdoor experience around Common Cause was delightful. It felt great to be active while soaking up the beautiful sights of Chestertown.
Jessica D.
A perfect date idea! We explored the George Vickers area and had an amazing time discovering new places together in our charming town.
David B.
This was a great family activity in downtown Chestertown. We all enjoyed learning about George Washington while having fun together.
Sarah W.
What a fantastic experience in the heart of Chestertown. The Revolution on the River spot was stunning, and I loved every moment of this self-guided tour.
Michael S.
I had a blast exploring the Chestertown Historic District. This walking tour was such a fun way to discover local history and hidden gems.
Emily J.
We had an awesome time with ScavengerHunt.com discovering cool places in Downtown. A must-try for anyone looking for fun things to do!
Brian L.
Such a fun thing to do with friends! The app guided us through fascinating locations, making our day in Chestertown unforgettable.
Olivia C.
This walking tour of Downtown Chestertown was amazing! We saw landmarks we never knew existed, making it a memorable adventure.
James L.
Exploring the Common Cause area was such a great experience. I loved uncovering local stories and hidden spots in this historic neighborhood.
Laura H.
I highly recommend this Chestertown tour for tourists. It offers unique insights into the area's rich heritage and culture.
Daniel G.
This outdoor activity in Downtown was delightful! We soaked up some sun while exploring iconic sites like George Vickers.
Jessica M.
The self-guided tour around John Leeds Barroll's home was such an interesting experience. I loved learning about local history.
David W.
We enjoyed a lovely date night wandering through Downtown Chestertown. The history and scenery made it so special.
Sarah D.
What a fun way to discover the Revolution on the River! This experience was perfect for our family day out in the charming town.
Michael S.
I had a fantastic time exploring the Chestertown Historic District. The walking tour was engaging and full of hidden gems.
Emily J.
FAQs.
What are some fun Outdoor Activities in Chestertown?
Are scavenger hunts good for groups in Chestertown?
I am new to Chestertown what do you recommend?
I am a Chestertown local would this be fun for me?
What is the full list of all the scavenger hunts and activities that I can do in Chestertown
LOCAL INSIGHTS
Fun Chestertown Facts and Hidden Gems
Chestertown was founded in 1706 as a thriving colonial port along the Chester River—a vital link between Chesapeake Bay trade routes.
Each spring, locals reenact the legendary Tea Party protest that helped spark revolutionary spirit across Maryland. You might be surprised by just how much living history shapes today’s welcoming vibe!
Each spring, locals reenact the legendary Tea Party protest that helped spark revolutionary spirit across Maryland. You might be surprised by just how much living history shapes today’s welcoming vibe!
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