Experience pure excitement as you explore Chestertown Scavenger Hunt and Washington College Scavenger Hunt alongside iconic landmarks and hidden gems—from vibrant street art to historic plazas.
Gather your crew for trivia quests, bold photo dares, and wild scavenger challenges that rack up points in our sleek app—compare scores and celebrate victories together!
Top Outdoor Activities In Chestertown, Maryland
Step onto the quaint brick streets of Chestertown, where Chesapeake Bay breezes mingle with centuries-old stories. In this Colonial Riverfront gem, outdoor activities invite you to uncover hidden corners and local legends while soaking up vibrant waterfront charm. Whether you are a visitor or a proud local, our experiences offer an unforgettable way to view Chestertown from new angles. Adventure awaits around every corner—get ready for fun-filled discoveries!
Outdoor Experiences in Chestertown, Maryland
Get ready to embark on a journey through Chestertown with our expertly curated list of outdoor activities! Each experience is designed to reveal the town's unique character, blending history, art, and adventure into every stop. From lively college avenues to picturesque riverfronts, these activities promise excitement for families, friends, and solo explorers alike. Dive in and see how sightseeing transforms into playful exploration with challenges and surprises at every turn.
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,...
5.0 (14 reviews)
Fly High, Hunt Higher: The Washington College Hunt
Washington College, Chestertown
Adventure awaits at Washington College! Hunt through books, statues, stages, and...
An epic Chestertown, Maryland experience
How Our Chestertown, Maryland Outdoor Activities Work
Our expert team has researched over 3,050 cities—including 50+ across Southeast—to craft each unique outdoor activity just for you. Every experience features clear instructions, custom routes tailored by locals, challenge quizzes at key sites like museums or parks.
During each activity in Chestertown your group explores on foot: answer trivia at historic markers, snap photos at murals along scenic streetscapes, solve puzzles at public installations—all tracked by our award-winning app so you can earn points and compare scores citywide.
Top Outdoor Attractions In Chestertown
Chestertown attractions come alive when you step outside—explore historic downtown's red-brick walkways, marvel at riverside vistas along the Chester River Adventures route, and soak in the energy near Washington College Town. Each spot offers must-see moments: discover art galleries tucked beside colonial buildings and enjoy live music wafting from bustling squares. Outdoor activities bring these sites together for an immersive day trip or weekend getaway bursting with fun things to do. 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.
George Washington statue
Discover outdoor fun in Chestertown along the Colonial Riverfront. Wander quaint brick streets and soak up Kent County's heart. Locals say the river breeze brings luck on your first visit.
Middle Hall
Enjoy Chestertown's outdoor energy at the Tea Party Festival Hub, where live music fills the air. The Chester River Adventures launch here, and locals recommend watching for herons by the water.
Miller Library
Stroll along Chestertown's waterfront heritage paths, where Eastern Shore charm shines. Outdoor things to do include spotting unique boats—locals say sunrise is especially magical here.
Gibson Center for the Arts
Explore Kent County's heart at this open-air spot, surrounded by colonial architecture and lively markets. Outdoor activities include people-watching—insiders know market day brings hidden gems.
Roy Kirby Stadium
Unwind outdoors near Chesapeake Bay Gateway, where gentle breezes meet scenic trails. Locals suggest listening for church bells echoing through historic downtown during your walk.
Johnson Fitness Center
Step into Chestertown's past with an outdoor adventure among colonial facades and leafy parks. Recommended by locals: look for hidden plaques telling tales of famous festival moments.
See our Top Outdoor Activities By Neighborhood
Discover how outdoor activities in Chestertown's top neighborhoods bring out the best of Kent County's heart—from waterfront heritage spots to cozy Eastern Shore corners filled with charm. For your next adventure or family outing, 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...
5.0 (1 reviews)
Washington College
Washington College, Chestertown
Experience the heart of Chestertown at Washington College, where historic landmarks like Middle Hall and the Gibson Center for the Arts create a vibrant atmosphere. This...
See what people say about our outdoor activities in Chestertown
Locals and visitors rave about our outdoor activities in Chestertown! With stellar star ratings and enthusiastic reviews like 'We discovered so many hidden gems,' it is easy to see why families keep coming back for more fun. Trust our team for memorable experiences that showcase what makes this city special.
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
Did you know Chestertown was founded in 1706 as a vital port on Maryland’s Eastern Shore? It's storied past includes hosting the legendary Tea Party Festival—a spirited nod to it's revolutionary roots.
Today, those same cobblestone streets echo with tales of artists, students from Washington College, and river captains who helped shape this ‘S
Today, those same cobblestone streets echo with tales of artists, students from Washington College, and river captains who helped shape this ‘S
© 2016-2025 Let's Roam, LLC. Let’s Roam® is a registered trademark. All Rights Reserved.
✕
Unlock An Extra 10% OFF Your First Order
You're Halfway To An Extra 10% OFF
Sign up for emails & texts to get your code
By submitting this form, you agree to receive recurring automated promotional and personalized marketing text messages (e.g. cart reminders) at the cell number used when signing up. Consent is not a condition of any purchase. Msg frequency varies. Msg and data rates may apply. Reply HELP for help and STOP to cancel. First time users only. Does not apply to custom events.
By submitting, you agree to receive recurring automated promotional/personalized marketing text messages (e.g. cart reminders). Msg/data rates may apply. Reply STOP to cancel.