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THINGS TO DO

Visitors to HISTORIC LEONARDTOWN will be charmed by its warm hospitality and vibrant energy. Discover specialty shops, fine dining, outdoor concerts, art shows, wine tastings, exciting watersports, and one-of-a-kind events like an Annual End of Summer Beach Party Blowout where you'll find a man-made beach made of 40 tons of sand right in the center of town and so much more. Click on a link below for more information and plan a visit to Leonardtown today. Other resources are available in our Planning section or contact Brandy Blackstone, the
Public Relations & Events Coordinator at brandy.blackstone@leonardtownmd.gov or 301-475-9791.

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EVENTS & HAPPENINGS

Concerts, Festivals, Boat Regattas, Parades, Virtual Programming and More!

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ATTRACTIONS

Exciting Activities from sunset cruises, and Kayak/Canoe Rentals, to a picturesque Wharf and a Winery.

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DINING

Discover Neghborhood Coffee Shops, Deli's, Cafés, a Winery, Alfresco Dining and World-Class Restaurants.

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SHOPPING

Eclectic Specialty Shops, Galleries, Coastal Art Markets, and a Can't Miss Indoor Marketplace.

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BUTTERFLY TRAIL

Discover Historic Landmarks, outdoor sculptures and works of art by local artists, and exciting activities in the Butterfly & kid's Caterpillar Trails. 

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WINE TRAIL

Featuring Southern Maryland Wineries and Vineyards. Tour the vineyards and enjoy live music while sampling award-winning wines.

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DAY AND SUNSET CRUISES AT THE WHARF

Enjoy a two-hour cruise down Breton Bay to St. Clements Island with Fish the Bay Charters. Departing from Leonardtown Wharf, these BYOB, small-group cruises on the Lisa S. are a great way to relax and connect with friends and family. Spend 2 hours cruising aboard the Lisa S., a 48-foot vintage charter boat, with Captain Phil Langley. Bring your favorite snacks, drinks and adult beverages on board or pick up something on your way from one of our wonderful local restaurants and dine while enjoying the sights and sounds of St. Mary's County's beautiful waterways.

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VIRTUAL GOLF/
GOLF INSTRUCTION

Looking for something different to do for your next outing? Why not try Above Par Golf  - a locally based company offering golf instruction and camps for kids and adults, virtual golf and multisport simulator rentals, a 500 sf putting green practice area and more. Golf merchandise available and club fittings and regrips coming in the near future.

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PORT OF LEONARDTOWN WINERY

Spend a relaxing day or wind down for the evening at the Port of Leonardtown Winery. Sample award-winning wines or non-alcohol or frosé slushies while listening to live music. This charming Winery is nestled within the Port of Leonardtown Winery Park. Amenities include an outdoor pavilion with colorful umbrellas for shade, cornhole and other games, an indoor patio with fire pit to keep you warm on cooler evenings and a tasting room. Sample eats from local food trucks and vendors or pick something up from one of our local restaurants in Town. 

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ART GALLERIES WORKSHOPS & CLASSES

The Town of Leonardtown, the only ARTS & ENTERTAINMENT DISTRICT in Southern Maryland, offers a rich experience in culture. Explore art galleries, see shows and attend art shares with upcoming and prominent artists, take group or one-on-one art classes, and create your own work of art in instructor-led workshops. If you love music and dance, you don't want to miss the Leonardtown Summer Music Festival - an exciting outdoor concert series that provides a summer of music and dance performances in venues throughout  historic Leonardtown from Leonardtown Square to Leonardtown Wharf. Visit the Arts & Entertainment Directory at the Learn More link below to find out about local art galleries, workshops and classes.

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MCINTOSH RUN

Rent a canoe or kayak from Pac Paddle Sports enjoy a day paddling along beautiful Breton Bay. A popular outing is along McIntosh Run, a picturesque water trail that leads all the way to Leonardtown Wharf and back. Travel a narrow creek under a canopy of trees along serene waterways that are home to Bald eagles, beavers, muskrats, and otter. Paddle with friends or meet others in regular group paddles and special events - frequent events include moonlight or sunrise paddles and other special events.

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WELLNES AND AQUATICS CENTER ON CSM's LEONARDTOWN CAMPUS

The St. Mary’s County Recreation & Parks Wellness & Aquatics Center (WAC) located at College of Southern Maryland’s Leonardtown Campus offers a variety of activities for the whole family.  The facility includes a 25-yard competition pool, warm water therapy pool with zero depth entry, a weight training room and 2 group fitness/dance studios. Daily entrance and membership passes are available for all ages.

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Featured LBA Business

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