Enjoy a two-hour sunset 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.

Visit Moll 'Dyer Rock at Tudor Hall Manor. This local landmark is believed to hold the now-fading handprint of local legend Moll Dyer, a local healer who died under tragic circumstances after being accused of witchcraft in the late 1600's. Many visit the site and leave gifts and trinkets for Moll at its new site at Tudor Hall Manor, but beware, many believe that those who touch the rock will be cursed by Moll. Mark your calendars and join us on February 26th for Moll Dyer Day, a soon to be three-day celebration filled with festivities from scavenger hunts, ghost walks, paranormal tours, and more.

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. 

Rent a canoe or kayak from Patuxent Adventure Center 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.