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. The dates for this season will be announced soon.

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.

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

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. 

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.

For those looking for fun and excitement will enjoy an outing to Viking Axe Throwing, located in the Brudergarten at Shepherd's Old Field Market. Try your hand at axe throwing, archery, and target shooting. The warm and friendly staff provide expert guidance to help get you started. Enjoy tasty eats and cocktails from the Brudergarten between sets. Looking for a challenge, why not join a league and compete with other area Vinkings. For  hours and booking info visit: Viking Axe Throwing.

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.

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.

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.