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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.

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Obraz karty poszukiwania skarbów Chestertown Chasers
zielona gwiazda 5.0 (16 recenzji)

Scavenger Hunt Chestertown Chasers‘ Treasure Hunt

Centrum, Chestertown

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

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The Chestertown Challenge card image
zielona gwiazda 5.0 (14 recenzji)

The Chestertown Challenge

Washington College, Chestertown

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

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Lataj wysoko, poluj wyżej: karta polowania na Washington College
zielona gwiazda 5.0 (14 recenzji)

Lataj wysoko, poluj wyżej: Polowanie na Washington College

Washington College, Chestertown

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

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o aktywnościach na świeżym powietrzu

WycieczkaepickieChestertown, Maryland experience

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.
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.

Mężczyzna na spacerze z poszukiwaniem skarbów

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.

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Obrazek karty z Dolnego Manhattanu
zielona gwiazda 5.0 (1 recenzja)

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...

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Karta z college'u Washington College
zielona gwiazda 5.0 (1 recenzja)

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...

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Karta z college'u Washington College
zielona gwiazda 5.0 (1 recenzja)

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...

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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.

5 gwiazdek recenzji

Using ScavengerHunt.com made exploring downtown so enjoyable! It guided us through interesting spots we might have missed otherwise.

William L.

5 gwiazdek recenzji

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.

5 gwiazdek recenzji

This experience was truly unique! I loved how interactive it was, especially getting to see John Leeds Barrolls historical significance.

James M.

5 gwiazdek recenzji

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.

5 gwiazdek recenzji

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.

5 gwiazdek recenzji

The outdoor experience around Common Cause was delightful. It felt great to be active while soaking up the beautiful sights of Chestertown.

Jessica D.

5 gwiazdek recenzji

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.

5 gwiazdek recenzji

This was a great family activity in downtown Chestertown. We all enjoyed learning about George Washington while having fun together.

Sarah W.

5 gwiazdek recenzji

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.

5 gwiazdek recenzji

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.

5 gwiazdek recenzji

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.

5 gwiazdek recenzji

Such a fun thing to do with friends! The app guided us through fascinating locations, making our day in Chestertown unforgettable.

Olivia C.

5 gwiazdek recenzji

This walking tour of Downtown Chestertown was amazing! We saw landmarks we never knew existed, making it a memorable adventure.

James L.

5 gwiazdek recenzji

Exploring the Common Cause area was such a great experience. I loved uncovering local stories and hidden spots in this historic neighborhood.

Laura H.

5 gwiazdek recenzji

I highly recommend this Chestertown tour for tourists. It offers unique insights into the areas rich heritage and culture.

Daniel G.

5 gwiazdek recenzji

This outdoor activity in Downtown was delightful! We soaked up some sun while exploring iconic sites like George Vickers.

Jessica M.

5 gwiazdek recenzji

The self-guided tour around John Leeds Barrolls home was such an interesting experience. I loved learning about local history.

David W.

5 gwiazdek recenzji

We enjoyed a lovely date night wandering through Downtown Chestertown. The history and scenery made it so special.

Sarah D.

5 gwiazdek recenzji

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

Michael S.

5 gwiazdek recenzji

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.

LOKALNE WSKAZÓWKI

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

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