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 towns 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.

Scavenger Hunt Chestertown Chasers‘ Treasure Hunt

Centrum, Chestertown


Chestertown‘s treasure ain‘t just George Washington‘s dentures! Discover hidden gems...


The Chestertown Challenge

Washington College, Chestertown


Experience a self-guided, app-led Washington College tour with trivia, photo challenges,...


Lataj wysoko, poluj wyżej: Polowanie na Washington College

Washington College, Chestertown


Adventure awaits at Washington College! Hunt through books, statues, stages, and...


WycieczkaepickieChestertown, Maryland experience

Zbierz swoją ekipę na quizy wiedzy, odważne wyzwania fotograficzne i szalone zadania typu scavenger hunt, które zdobywają punkty w naszej eleganckiej aplikacji — porównujcie wyniki i wspólnie świętujcie zwycięstwa!
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

Atrakcje Chestertown ożywają, gdy wyjdziesz na zewnątrz — odkryj brukowane alejki zabytkowego centrum, podziwiaj nadbrzeżne widoki wzdłuż trasy Chester River Adventures i chłoń energię w pobliżu Washington College Town. Każde miejsce oferuje momenty warte zobaczenia: odkrywaj galerie sztuki ukryte obok kolonialnych budynków i ciesz się muzyką na żywo płynącą z tętniących życiem placów. Aktywności na świeżym powietrzu łączą te miejsca, tworząc wciągający jednodniowy wypad lub weekendowy wyjazd pełen wspaniałych rzeczy do zrobienia. Kliknij każde miejsce, aby zobaczyć powiązane aktywności.

George Vickers


 Discover the George Vickers plaque in Chestertowns historic downtown. Locals say his spirit echoes through the Blue Crab Festival. Enjoy a day trip filled with history and charm.


John Leeds Barroll


 Odwiedź pomnik Johna Leedsa Barrolla, obowiązkowy punkt dla miłośników historii. To miejsce kiedyś tętniło życiem dzięki wartym uwagi opowieściom. Ciesz się artystycznym spacerem po Main Street i poczuj atmosferę Waszyngtońskiego Miasta Uniwersyteckiego.


Dzielnica Historyczna Chestertown


 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.


Wspólna sprawa


 Visit the Common Cause marker, buzzing with Revolutionary energy during Mays Tea Party reenactment. Capture the spirit of Kent Countys 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.


Rewolucja na rzece


 Stand where townsfolk once defied Britain by dumping tea into Chester River—a Chesapeake Bay Gateway experience! Feel historys echoes on breezy days at this Eastern Shore Adventure Spot.


Pomnik Williama Becka Nicholsona


 Enjoy Chestertowns 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.


Publiczna Szkoła w Chestertown


 Wander the Eastern Shore and soak in Chestertowns vibrant outdoor scene. Spot hidden murals or catch the Tea Party Festival hub energy—perfect for first-time visitors craving something memorable.


Pomnik George'a Washingtona


 Explore Kent Countys heart by the water, where locals gather for riverside picnics and laughter echoes off the docks. Outdoor activities here offer a taste of Chestertowns waterfront heritage.


Miller Library


 Step onto Chestertowns 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.


Centrum Sztuki Daniela Z. Gibsona


 Breathe in fresh river air while exploring Chestertowns scenic pathways. Outdoor enthusiasts love the blend of waterfront heritage and hidden gems tucked along these inviting routes.


Pomnik George'a Washingtona


 Discover outdoor fun in Chestertown along the Colonial Riverfront. Wander quaint brick streets and soak up Kent Countys heart. Locals say the river breeze brings luck on your first visit.


Środkowa Hala


 Enjoy Chestertowns 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 Chestertowns 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 Countys 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


 Wejdź w przeszłość Chestertown dzięki przygodzie na świeżym powietrzu wśród kolonialnych fasad i zielonych parków. Polecane przez miejscowych: szukaj ukrytych tablic opowiadających historie o słynnych momentach festiwali.


Zobacz nasze najlepsze aktywności na świeżym powietrzu według dzielnic

Discover how outdoor activities in Chestertowns top neighborhoods bring out the best of Kent Countys 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.

Śródmieście

Centrum, Chestertown



 Discover the must-see sights of Downtown Chestertown. With its quaint brick streets and historic landmarks like George Washingtons influence, it is a top attraction...


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...


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 Barrolls 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 areas 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 Barrolls 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.

Co za wspaniały sposób na odkrycie Rewolucji na Rzece! To doświadczenie było idealne na nasz rodzinny wypad do urokliwego miasteczka.

Michael S.

I had a fantastic time exploring the Chestertown Historic District. The walking tour was engaging and full of hidden gems.

Emily J.

Często zadawane pytania.

 
What are some fun Outdoor Activities in Chestertown?

 
Are scavenger hunts good for groups in Chestertown?

 
Jestem nowy w Chestertown, co polecasz?

 
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

 
Fun Chestertown Facts and Hidden Gems

Today, those same cobblestone streets echo with tales of artists, students from Washington College, and river captains who helped shape this ‘S
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