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.

切斯特敦追逐者寻宝游戏

市中心,切斯特敦


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


切斯特敦挑战

华盛顿学院,切斯特敦 (Washington College, Chestertown)


体验一次自助式、应用程序引导的华盛顿学院之旅,包含问答题、摄影挑战,...


飞得更高,寻宝更高:华盛顿学院寻宝

华盛顿学院,切斯特敦 (Washington College, Chestertown)


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


一个史诗般的Chestertown, Maryland experience

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!
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.

乔治·维克斯


 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.


约翰·利兹·巴罗尔


 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.


切斯特敦历史区


 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.


共同事业


 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.


乔治·华盛顿


 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.


河上革命


 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.


威廉·贝克·尼科尔森雕像


 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.


切斯特敦公立学校塔楼


 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.


乔治·华盛顿雕像


 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.


米勒图书馆


 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.


丹尼尔·Z·吉布森艺术中心


 呼吸清新的河畔空气,探索切斯特敦的风景小径。户外爱好者们喜欢这里融合了海滨遗产和隐藏在迷人路线中的宝藏。


乔治·华盛顿雕像


 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.


Middle Hall


 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.


米勒图书馆


 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.


吉布森艺术中心


 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.


罗伊·柯比体育场


 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.


约翰逊健身中心


 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.


查看我们按社区划分的顶级户外活动

探索切斯特敦顶级社区的户外活动如何展现肯特县心脏的最佳风貌——从海滨遗产景点到充满魅力的舒适东岸角落。对于您的下一次冒险或家庭出游,请点击这些社区以查看相关活动。

市中心

市中心,切斯特敦



 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...


华盛顿学院

华盛顿学院,切斯特敦 (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...


华盛顿学院

华盛顿学院,切斯特敦 (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.

威廉·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.

索菲亚·H.

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

詹姆斯 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.

杰西卡·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.

迈克尔·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.

艾米莉·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!

布莱恩 L.

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

奥利维亚·C。

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

詹姆斯·L。

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

劳拉·H。

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

丹尼尔·G。

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

杰西卡·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.

迈克尔·S。

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

艾米莉·J。

常见问题解答。

 
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?

 
切斯特敦所有寻宝游戏和活动有哪些完整的列表?

 
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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