U.S. Oyster Festival

St. Mary's County Fairgrounds 42455 Fairgrounds Rd, Leonardtown, MD

Next full scale Oyster Festival – October 16-17, 2021 at St. Mary’s County Fairgrounds. Gates open at 10 AM Saturday Oct 16 and close at 6pm. Gates open at 11 AM on Oct 17 and close at 6 PM. Please contact usoysterfestival@gmail.com for details. 

Veterans Day Parade

Leonardtown Square Leonardtown, Maryland

The Commissioners of St. Mary’s County and the Commissioners of Leonardtown invite the public to join the Town of Leonardtown in celebrating Veteran's Day with the largest Veteran's Day parade in Maryland! The parade steps off from St. Mary’s Ryken High School, proceeds through Town Square and is immediately followed by a Memorial Ceremony.

Free

Live Music at Port of Leonardtown Winery

Port of Leonardtown Winery 23190 Newtowne Neck Rd., Leonardtown, Maryland

The 80's are calling! Spend your Saturday afternoon drinking award winning wine and listening to great 80's music at Port of Leonardtown Winery. Come dance the afternoon away and try a tasty wine slushie at one of their outdoor patio seats or bring your own lawn chair and blanket!

Free

Christmas on the Square + Annual Tree Lighting

Leonardtown Square Leonardtown, Maryland

Get the holiday festivities started in Downtown Leonardtown. Come see the beautiful tree lighted for the holiday season and enjoy other fun things going on throughout the town! Your family and friends will enjoy the holiday music, entertainment, horse and carriage rides, sleigh rides, train rides, hayrides, live nativity, petting zoo, face painting, children’s crafts, […]

Free

First Friday in Leonardtown

Explore Downtown Leonardtown on First Friday! Come enjoy dinner at one of the many local restaurants, enjoy a drink from Social Coffeehouse or Antoinette's Garden, explore Shepherd's Old Field Market, shop at one of the many local shops and art galleries, and enjoy a sweet treat from Heritage Chocolates! There will be free trolley rides […]

Free

St. Clements Island Museum Christmas Doll & Train Exhibit

St. Clement’s Island Museum 38370 Point Breeze RoadColtons Point, Maryland 20626 13017692222 Admission: $3.00 Adults/$2.00 Seniors and Military/$1.50 Children/5 and under Free.Location: St. Clement's Island Museum Enjoy a holiday exhibit of antique and collectible dolls (like Barbie, American Girl and more), classic trains and other retro toys in this festive holiday display inside the museum from 12 […]

New Year’s Eve Dinner & Dance with Robbie Boothe!

Bowles Farm 22880 Budds Creek RdClements, Maryland 20624 Admission: $85 Per Person | Advance Tickets OnlyLocation: Bowles FarmTime:6:30 PM to 12:30 AM Join us at Bowles Farm for a New Years' Eve celebration enjoying good people, food, drinks, and live entertainment. The dinner features fried chicken, baked ham and sides, and an open bar. Put on those […]

Leonardtown’s First Friday

Admission: FreeLocation: Downtown LeonardtownTime:5:00 PM to 8:00 PM Explore Downtown Leonardtown on First Friday! Come enjoy dinner at one of the many local restaurants, enjoy a drink from Social Coffeehouse or Antoinette's Garden, explore Shepherd's Old Field Market, shop at one of the many local shops and art galleries, and enjoy a sweet treat from Heritage Chocolates! […]