Locations Maryland Chestertown

Top Outdoor Activities In Chestertown, Maryland

Q: What are some fun Outdoor Activities in Chestertown?

Some of the most fun outdoor activities in Chestertown include creative adventures through Historic Downtown and Washington College Town—perfect for sightseeing while enjoying trivia quests or photo challenges. These unique experiences immerse you in must-see attractions while keeping things fresh every time you visit.

Q: Are scavenger hunts good for groups in Chestertown?

Absolutely! Our group-friendly outdoor activities offer team-based challenges ideal for families or friends visiting Chestertown together. Explore Colonial Riverfront sights as teams tackle trivia questions—earning points along scenic routes makes it even more exciting! Gather your crew today for an unforgettable outing.

Q: I am new to Chestertown what do you recommend?

If you are new to visiting Chestertown start by checking out our recommended outdoor activities—they showcase both iconic landmarks like Kent County's Heart and hidden gems off Main Street. You will discover what makes this Chesapeake Bay Gateway truly special while having fun along the way.

Q: I am a Chestertown local would this be fun for me?

Locals love rediscovering their city through our interactive outdoor activities! Even if you have walked Quaint Brick Streets before—you might spot something new near Washington College or find secret murals tucked away Downtown . Try one today and see how much more there is to explore!

Q: What is the full list of all the scavenger hunts and activities that I can do in Chestertown

There are quire a few scavenger hunts and activities that we offer in Chestertown, here is a full list: Chestertown Maryland Scavenger Hunt: Chestertown Chasers‘ Treasure Hunt , Chestertown Maryland Scavenger Hunt: Fly High, Hunt Higher: The Washington College Hunt , Chestertown Maryland Scavenger Hunt: The Chestertown Challenge , Chestertown Bachelorette Party Ideas , Chestertown Maryland Tours , Chestertown Corporate Team Building Activities , and Chestertown Birthday Party Ideas

Step into Chestertown, Maryland, where the Chester River sparkles beside Colonial Riverfront and vibrant brick streets wind past centuries-old buildings. Outdoor activities in Chestertown invite you to uncover this Eastern Shore gem in unforgettable ways. Whether you are a visitor or local, these experiences offer the perfect blend of adventure and history. Discover why exploring Chestertown is a must-see for anyone seeking new things to do.

See Top Rated Chestertown Hunt Browse All Chestertown Activities

Adventurers exploring in Chestertown!

Chestertown Downtown

Chestertown Washington College

Chestertown Downtown

Chestertown Washington College

Chestertown Downtown

Chestertown Washington College

Chestertown Downtown

Chestertown Washington College

Chestertown Downtown

4.8/5 stars for 2,000 Adventurers in Chestertown & 5,000,000 ADVENTURERS Around The World

Outdoor Experiences in Chestertown, Maryland

Our expertly curated list of outdoor activities in Chestertown transforms every stroll into an adventure packed with discovery and excitement. Each experience is designed to showcase the city’s unique charm, from historic downtown corners to waterfront vistas. Expect interactive challenges that bring out your competitive spirit and spark laughter along the way. Dive into these recommended outdoor activities and let each step reveal a new side of Chestertown.

Top Rated

Chestertown Chasers‘ Treasure Hunt Scavenger Hunt card image

5.0 (283 reviews)

Chestertown Chasers‘ Treasure Hunt Scavenger Hunt

Downtown, Chestertown, Maryland

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

See Top Rated Chestertown Hunt

Fly High, Hunt Higher: The Washington College Hunt card image

5.0 (69 reviews)

Fly High, Hunt Higher: The Washington College Hunt

Washington College, Chestertown, Maryland

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

See Top Rated Chestertown Hunt

5.0 (66 reviews)

The Chestertown Challenge

Washington College, Chestertown, Maryland

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

See Top Rated Chestertown Hunt

More Hunts Nearby

Can't find what you're looking for in Chestertown? Check out these great scavenger hunts within 30 miles.

11.8 mi away

Centreville‘s Quaint Quest Scavenger Hunt card image

5.0 (272 reviews)

Centreville‘s Quaint Quest Scavenger Hunt

Downtown, Centreville, Maryland

Embark on a thrilling scavenger hunt in Centreville‘s Downtown, unveiling hidden gems &...

See Top Rated Chestertown Hunt

19.7 mi away

Kent Narrows Watery Scene Scavenger Hunt card image

5.0 (285 reviews)

Kent Narrows Watery Scene Scavenger Hunt

Downtown, Kent Narrows, Maryland

Crabby about adventure? Let us she'll out fun and discoveries as you solve clues on our...

See Top Rated Chestertown Hunt

20.7 mi away

Aberdeen Treasured Tales Scavenger Hunt card image

5.0 (269 reviews)

Aberdeen Treasured Tales Scavenger Hunt

Downtown, Aberdeen, Maryland

Aberdeen‘s got soul-diers of fun: unleash your inner general with our thrilling downtown...

See Top Rated Chestertown Hunt

22.7 mi away

Dundalk Dazzling Dash Scavenger Hunt card image

5.0 (467 reviews)

Dundalk Dazzling Dash Scavenger Hunt

Downtown, Dundalk, Maryland

Join us on a thrilling scavenger hunt in charming Dundalk‘s Downtown! Discover...

See Top Rated Chestertown Hunt

22.9 mi away

Havre de Dash & Discover Scavenger Hunt card image

5.0 (359 reviews)

Havre de Dash & Discover Scavenger Hunt

Downtown, Havre de Grace, Maryland

Let's put the "grace" in Havre de Grace! Our two-mile scavenger hunt will guide you...

See Top Rated Chestertown Hunt

24.6 mi away

Middletown‘s Dazzling Downtown Dash Scavenger Hunt card image

5.0 (266 reviews)

Middletown‘s Dazzling Downtown Dash Scavenger Hunt

Downtown, Middletown, Delaware

Explore Middletown’s storybook streets—where theaters, taverns, parks, and history...

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25 mi away

Charlestown Scavenger Hunt Scavenger Hunt card image

5.0 (273 reviews)

Charlestown Scavenger Hunt Scavenger Hunt

Downtown, North East, Maryland

North East ain‘t just a direction, it‘s a thrilling scavenger hunt experience in...

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25.2 mi away

Smyrna‘s Downtown Dazzling Dash Scavenger Hunt card image

5.0 (272 reviews)

Smyrna‘s Downtown Dazzling Dash Scavenger Hunt

Downtown, Smyrna, Delaware

Pottery & pearls, Smyrna‘s historic gems await! Join our scavenger hunt Downtown for...

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How Our Chestertown, Maryland Outdoor Activities Work

Our expert team researches over 3,050 cities—including 50+ across Southeast—to design unforgettable outdoor activity routes filled with must-sees and hidden treasures tailored just for each destination. Every activity includes clear instructions plus route maps guiding your journey through local highlights.

During each experience your group explores on foot—answering trivia at historical markers snapping photos at public art installations solving puzzles at famous sites—all tracked through our award-winning app so everyone can compare scores after conquering each challenge.

Top Outdoor Attractions In Chestertown

Chestertown’s top attractions come alive when explored through engaging outdoor activities that highlight it's rich heritage and lively culture. Wander bustling Historic Downtown, marvel at art galleries, or soak up live music near the riverfront as you uncover hidden stories at every turn. Washington College offers leafy paths steeped in academic tradition, while Kent County’s Heart pulses with local craft beer spots and family friendly fun. 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.

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.

See our Top Outdoor Activities By Neighborhood

Outdoor activities await throughout Chestertown’s most beloved neighborhoods—from quaint brick-lined streets to the vibrant energy of Washington College Town. Each area promises memorable sightseeing moments and unique adventures—click on these neighborhoods to see the related activity.

25.2 mi away

5.0 (1 reviews)

Downtown

Downtown, Chestertown, Maryland

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...

See Top Rated Chestertown Hunt

25.2 mi away

5.0 (1 reviews)

Washington College

Washington College, Chestertown, Maryland

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 Top Rated Chestertown Hunt

25.2 mi away

5.0 (1 reviews)

Washington College

Washington College, Chestertown, Maryland

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...

See Top Rated Chestertown Hunt

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12,000+ Reviews For our Hunts

See what people say about our outdoor activities in Chestertown

Visitors rave about our outdoor activities in Chestertown for their creativity, fun challenges, and memorable moments shared with friends or family. One happy guest said it was 'the best day trip ever—five stars all around!' See why locals and tourists alike trust us for top-rated experiences.

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 that Chestertown has been a hub for adventure since colonial times? Founded along the Chester River in 1706 as a major port town for Maryland's Eastern Shore trade routes—it still hosts famed events like the Tea Party Festival.

Today visitors can wander it's preserved historic district lined with red-brick sidewalks or explore n