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Top Outdoor Activities In Leonardtown, Maryland

Step into the charm of Leonardtown, Maryland, where every corner holds a story waiting to be discovered. Known as the Chesapeake Bay Getaway, this delightful town offers breathtaking views and vibrant culture. Our outdoor activities are the perfect way to explore Leonardtown's unique attractions, from iconic landmarks to hidden gems. Feel the excitement as you embark on adventures that bring history and fun together.

Adventurers exploring in Leonardtown!

Outdoor Experiences in Leonardtown, Maryland

Welcome to our expertly curated list of outdoor activities in Leonardtown! Each experience promises a unique blend of excitement and discovery, inviting you to dive into thrilling adventures. From exploring local history to uncovering hidden treasures, these activities offer something for everyone looking for an unforgettable day out.

Top Rated
Leonardtown Loot & Legends Hunt Scavenger Hunt card image
green star 5.0 (13 reviews)

Leonardtown Loot & Legends Hunt Scavenger Hunt

Downtown, Leonardtown, Maryland

Discover the hidden gems of Leonardtown's Downtown neighborhood on our thrilling scavenger...

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More Hunts Nearby

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

9.4 mi away
Patuxent Prowlers‘ Treasure Pursuit Scavenger Hunt card image
green star 5.0 (13 reviews)

Patuxent Prowlers‘ Treasure Pursuit Scavenger Hunt

West, Patuxent River, Maryland

Join us for a hilarious and exciting two-mile scavenger hunt in Patuxent River's West...

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9.5 mi away
Solomons‘ Secrets Scavenger Spectacle Scavenger Hunt card image
green star 5.0 (20 reviews)

Solomons‘ Secrets Scavenger Spectacle Scavenger Hunt

Downtown, Solomons, Maryland

Calling all Solomons adventurers! ...

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23.8 mi away
Point Lookout Scavenger Hunt Scavenger Hunt card image
green star 5.0 (14 reviews)

Point Lookout Scavenger Hunt Scavenger Hunt

Downtown, Scotland, Maryland

Ahoy, Ridge adventurers! Hunt for treasures in Downtown while discovering history &...

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24.4 mi away
Scotland, Maryland Ghost Hunt card image
green star 5.0 (23 reviews)

Scotland, Maryland Ghost Hunt

downtown ghost hunt, Scotland, Maryland

Embark on a self-guided ghost hunt in Scotland, Maryland with an app-led adventure full of...

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28.1 mi away
Chesapeake Charm & Coastal Quest Scavenger Hunt card image
green star 5.0 (16 reviews)

Chesapeake Charm & Coastal Quest Scavenger Hunt

Downtown, Chesapeake Beach, Maryland

Join our exciting scavenger hunt in downtown Chesapeake Beach, MD! Discover aquatic life,...

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about outdoor activities

An Epic Leonardtown, Maryland experience

Experience the thrill of exploring Leonardtown Scavenger Hunt alongside iconic landmarks or hidden gems in Leonardtown's vibrant streets.
Gather your team for trivia quests, photo dares, and scavenger challenges that make use of app-based scoring for social fun.
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How Our Leonardtown, Maryland Outdoor Activities Work

Our team has meticulously researched over 3,050 cities worldwide including 50+ locations across Southeast offering diverse range options tailored specifically towards enhancing visitor experience wherever go next whether museum challenge bar crawl city tour etc.

During each activity participants explore foot answering trivia questions solving puzzles participating photo tasks earn points unlock achievements via award-winning app compare scores against others.

Man on a scavenger hunt walking tour
Hunt Map Leonardtown
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Top Outdoor Attractions In Leonardtown

Discover the best of Leonardtown's outdoor attractions with our engaging activities that highlight the beauty and culture of this charming town. From historic sites like Tudor Hall Landmark to scenic spots along Breton Bay, each location offers it's own allure. Click on each location to see related activities.

1

The Old Jail Museum & Leonardtown Visitor Center

Explore the Old Jail Museum, a must-see for history enthusiasts. Discover tales of daring escapes and admire the original cell windows. A unique outdoor activity in Leonardtown.
2

World War I Memorial

Pause at the World War I Memorial to reflect on it's twin plaques that honor sacrifice. This outdoor site is perfect for a moment of gratitude during your Leonardtown visit.
3

Site of the Methodist Episcopal Meeting House

Discover the Historic Movie Theater, once bustling with townsfolk and moviegoers. It's an intriguing spot for outdoor exploration and connecting with Leonardtown's past.
4

Leonardtown Wharf

Stroll along Leonardtown Wharf, where locals gather for sunset concerts. Enjoy architecture spotting and capture stunning photos along the boardwalk—a vibrant outdoor activity.
5

St Mary's County Law Library

Outside the Law Library, imagine legal debates from days past. The courthouse clock's quirks add intrigue to your outdoor adventure in downtown Leonardtown.
6

Deceased Veterans Memorial

Pay respects at the Deceased Veterans Memorial, where each bronze name echoes local pride. A poignant outdoor stop on your journey through Maryland's Wine Country.
7

Tudor Hall

Tudor Hall's gardens bloom beautifully each spring, making it an ideal first stop on your outdoor city tour. Enjoy this cheerful landmark's charm in Leonardtown.
1

The Old Jail Museum & Leonardtown Visitor Center

Explore the Old Jail Museum, a must-see for history enthusiasts. Discover tales of daring escapes and admire the original cell windows. A unique outdoor activity in Leonardtown.
2

World War I Memorial

Pause at the World War I Memorial to reflect on it's twin plaques that honor sacrifice. This outdoor site is perfect for a moment of gratitude during your Leonardtown visit.
3

Site of the Methodist Episcopal Meeting House

Discover the Historic Movie Theater, once bustling with townsfolk and moviegoers. It's an intriguing spot for outdoor exploration and connecting with Leonardtown's past.

See our Top Outdoor Activities By Neighborhood

Explore the vibrant neighborhoods of Leonardtown through our exciting outdoor activities. Each area has it's own character and charm, offering unique experiences for visitors and locals alike. Click on these neighborhoods to see the related activity.

28.1 mi away
Downtown card image
green star 5.0 (1 reviews)

Downtown

Downtown, Leonardtown, Maryland

Leonardtown's Downtown is a must-see for visitors seeking unique things to do. With landmarks like Tudor Hall and Breton Bay views, it promises an engaging sightseeing...

See Top Rated Leonardtown Hunt
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12,000+ Reviews For our Hunts

See what people say about our outdoor activities in Leonardtown

Trust in our outdoor activities is built on countless happy customers who have shared their experiences in Leonardtown. With glowing testimonials and stellar star ratings, it is clear why people love what we offer here. Discover why our adventures stand out!

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We had such a great time exploring the Site of the Methodist Episcopal Meeting House. It’s truly one of those unique things to do in Leonardtown.
James W.
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Leonardtown is full of surprises! This tour helped us uncover iconic sites we never knew existed, making it a must-do experience.
Sophia L.
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A great family-friendly activity in the heart of Leonardtown! We learned so much while having fun together on this interactive tour.
Chris H.
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Our scavenger hunt in Leonardtown was an amazing experience! The app guided us through fascinating historical locations.
Laura M.
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We discovered so many cool spots during our walking tour around the Deceased Veterans Memorial. Highly recommend this thing to do!
Daniel G.
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This was a fantastic way to see the highlights of Downtown Leonardtown. I loved every moment of this engaging experience.
Jessica D.
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Exploring Leonardtown Wharf was such a delightful outdoor activity. The scenery and history made it memorable.
David B.
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The Old Jail Museum was an interesting stop on our self-guided tour. A great experience for families looking for things to do.
Sarah W.
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What a fun date idea in the heart of Leonardtown. We enjoyed discovering hidden gems while strolling through the historic streets.
Michael S.
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I had a blast exploring Tudor Hall during our walking tour. It was a unique way to learn about Leonardtown's rich history.
Emily J.
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Loved using the ScavengerHunt.com app for our adventure! It made exploring the charming streets of Leonardtown super enjoyable.
Kevin W.
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A great way to enjoy the highlights of downtown Leonardtown! This interactive tour made learning about history so much fun.
Laura L.
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This scavenger hunt was such a cool thing to do in Leonardtown. We found interesting landmarks we never knew existed!
Brian H.
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What a fantastic experience! The walking tour allowed us to explore iconic spots like the World War I Memorial in downtown.
Ashley M.
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We had an amazing time on our self-guided tour of St Mary's County Law Library. A unique way to see the historic charm of Leonardtown.
Chris G.
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Exploring Leonardtown Wharf was such a fun outdoor activity. The views were stunning, and we discovered some hidden gems.
Jessica D.
star star star star star
A perfect date idea for us! We enjoyed walking around Tudor Hall and learning about its history. Highly recommend this experience!
David B.
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This is a great family activity in Leonardtown. We loved discovering unique spots together and making memories.
Sarah W.
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The Old Jail Museum was fascinating. It was a fun way to learn about local history while enjoying the sights of downtown.
Michael S.
star star star star star
I had a blast exploring the Deceased Veterans Memorial on this walking tour. Such a meaningful experience in Leonardtown.
Emily J.

FAQs.

LOCAL INSIGHTS

Fun Leonardtown Facts and Hidden Gems

Leonardtown boasts a rich history dating back to it's founding as a port town along the Potomac River. Known for it's role during the War of 1812, this charming locale has evolved into a hub for art galleries and craft beer enthusiasts alike.

Did you know that St. Mary's County Seat is home to one of Maryland's oldest wineries? This adds yet a
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Founders Charlie and Mike
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