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 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.
Mais Bem Avaliado
5.0 (16 avaliações)
Caça ao Tesouro 'Chestertown Chasers‘ Treasure Hunt'
Centro da cidade, Chestertown
Chestertown‘s treasure ain‘t just George Washington‘s dentures! Discover hidden gems...
5.0 (14 avaliações)
The Chestertown Challenge
Washington College, Chestertown
Experience a self-guided, app-led Washington College tour with trivia, photo challenges,...
5.0 (14 avaliações)
Voa Alto, Caça Mais Alto: A Caça da Washington College
Washington College, Chestertown
Adventure awaits at Washington College! Hunt through books, statues, stages, and...
UmépicoChestertown, 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 downtowns 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 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
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.
Distrito Histórico de 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.
Causa Comum
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.
Revolução no Rio
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.
Estátua de William Beck Nicholson
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.
Torre da Escola Pública de 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.
Estátua de George Washington
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.
Biblioteca Miller
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.
Daniel Z. Gibson Center for the Arts
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.
Estátua de George Washington
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.
Salão do Meio
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.
Biblioteca Miller
Passeie pelos caminhos históricos à beira-mar de Chestertown, onde o charme da Costa Leste brilha. Coisas ao ar livre para fazer incluem avistar barcos únicos — os locais dizem que o nascer do sol é especialmente mágico aqui.
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
Step into Chestertowns past with an outdoor adventure among colonial facades and leafy parks. Recommended by locals: look for hidden plaques telling tales of famous festival moments.
Veja Nossas Melhores Atividades ao Ar Livre por Bairro
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.
Mais Bem Avaliado
5.0 (1 avaliações)
Centro
Centro da cidade, 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...
5.0 (1 avaliações)
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 avaliações)
Washington College
Washington College, Chestertown
Explore o coração de Chestertown na Washington College, onde marcos históricos como o Middle Hall e o Gibson Center for the Arts criam uma atmosfera vibrante. Esta...
Veja o que as pessoas dizem sobre nossas atividades ao ar livre em 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.
Esta experiência foi verdadeiramente única! Adorei o quão interativa foi, especialmente por poder ver a importância histórica de John Leeds Barroll.
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.
Esta atividade ao ar livre no centro foi deliciosa! Aproveitamos o sol enquanto explorávamos locais icônicos como 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.
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.
Perguntas Frequentes.
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?
Qual é a lista completa de todas as caças ao tesouro e atividades que posso fazer em Chestertown
INSIGHTS LOCAIS
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® é uma marca registrada. Todos os Direitos Reservados.
Idioma Local
✕
Desbloqueie 10% DE DESCONTO EXTRA no seu primeiro pedido
Você está na metade do caminho para um desconto extra de 10%
Cadastre-se para e-mails e SMS para receber seu código
Ao enviar este formulário, você concorda em receber mensagens de texto promocionais e de marketing personalizadas recorrentes automatizadas (ex: lembretes de carrinho) no número de celular usado ao se inscrever. O consentimento não é uma condição de compra. Frequência de mensagens varia. Podem aplicar-se tarifas de mensagens e dados. Responda HELP para ajuda e STOP para cancelar. Apenas para usuários de primeira viagem. Não se aplica a eventos personalizados.
Ao enviar, você concorda em receber mensagens de texto promocionais/marketing personalizadas recorrentes automatizadas (ex: lembretes de carrinho). Podem aplicar-se tarifas de mensagens/dados. Responda STOP para cancelar.