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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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DINING

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

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WHERE TO STAY

Leonardtown has its very own hotel  - The Inn at Leonardtown, a luxurious, 40-room boutique hotel in the heart of Leonardtown, right off Leonardtown Square. You'll be in walking distance of all the activity.

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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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LUXURY PICNICS WITH PICNICS WITH A TWIST

Available starting in the Spring of 2022 enjoy luxury picnics with your friends and loved ones at the Leonardtown Wharf or the Port of Leonardtown Park courtesy of Picnics with a Twist offering romantic date nights, sip and paint parties, bridal and baby showers, engagement settings and more. When you want to make a special occasion even more special, make it a Picnic with a Twist. For more information or bookings visit: Picnics with a Twist

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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. 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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LUXURY PICNICS FROM FULL BLOOM AESTHETICS

Full Bloom Aesthetics offers an elegant/luxury pop up picnic experience for all occasions from bridal and baby showers, girls night out, engagement, announcements and more. Now experience the Full Bloom luxury for yourself at the Leonardtown Wharf and the Port of Leonardtown Park (available starting in the Spring of 2022). For more information visit us on Instagram at: Full Bloom Aesthetics

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MCINTOSH RUN

Rent a canoe or kayak from Pac Paddle Sports (Paxadventure.com) 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 entire 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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PLACES TO SEE

There's so much to see and experience in Historic Leonardtown from Leonardtown Square, the heart of this warm and friendly town, the vibrant energy of Shepherds Old Field Market, the hip and eclectic vibe of Fenwick Street, the peaceful tranquility of Port of Leonardtown Winery Park, and the serenity of beautiful Leonardtown Wharf. Come back again and again to discover all that Historic Leonardtown has to offer.

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ACTION BILLIARDS & LOUNGE

A full-service restaurant and bar offering 18 diamond pool tables, indoor corn hole, darts and more!

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BRUDERGARTEN
BEER GARDEN

An indoor/outdoor beer garden. Bru frequently hosts live music and special one-of-a-kind events such as Viking Axe Throwing, Bruderfest (the Bru's take on Octoberfest) and more.

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ESCAPE ROOMS
SOUTHERN MARYLAND

Enjoy clue based escape adventures offering a variety of themes. A great team-building activity or outing for the entire family.

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BRETON BAY GOLF COURSE & COUNTRY CLUB

Golf course and country club that houses , a full-service restaurant called the Ironwood Grill, a full-service Pro shop, aquatics facility offering a large competition pool, and four tennis courts. The gold course and restaurant are open to the public.

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RIDE THE LEONARDTOWN TROLLEY FOR FREE

Now it's easier to get around to all the great dining, shopping and activities in Leonardtown. You can ride the Leonardtown Trolley FREE all summer long (provided by Patuxent Transportation, LLC and courtesy of our valued sponsors). So, save on gas and ride the trolley around Town to enjoy the specialty shops, fine dining, exciting activities and fun!

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VISITOR CENTER/
OLD JAIL MUSEUM

Begin your visit to Leonardtown at the Old Jail Museum and new Leonardtown Visitor's Center to learn all the wonderful things there are to see and do in this vibrant Southern Maryland Town. 

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Featured LBA Business

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