Southern Maryland Communities Gear Up For A Season Of Food And Fall Fun

Fall events happening in southern maryland 2025 — Photo Credit: U.S. Oyster Festival, Charles County Fair, St. Mary’s County Fair

CALIFORNIA, Md. — As summer fades, Southern Maryland is gearing up for a season filled with fairs, festivals, seafood feasts and family traditions across Charles, St. Mary’s and Calvert counties.

In Charles County, the season opens with the Charles County Fair, Sept. 11–14 in La Plata, a beloved annual celebration of agriculture that features livestock shows, 4-H competitions, carnival rides and plenty of fair food favorites. Later in the season, food takes center stage at SoMD Savor the Flavor on Oct. 26 in Newburg, a riverfront showcase where local chefs and restaurants highlight Southern Maryland’s signature cuisine.

In St. Mary’s County, tradition continues with the St. Mary’s County Fair, Sept. 18–21 in Leonardtown, where families can enjoy parades, horse pulls, funnel cakes and local seafood. The county also hosts Indigenous Heritage Day at Historic St. Mary’s City on Sept. 6, a celebration of Piscataway culture through food, music and storytelling. Later in the month, RiverFest and Militia Muster on Sept. 27 will bring colonial reenactments, waterfront activities and seasonal fare. And in October, the U.S. Oyster Festival, Oct. 18–19 in Leonardtown returns with the U.S. National Oyster Shucking Championship and an abundance of raw, fried and roasted oysters.

In Calvert County, the Calvert County Fair, Sept. 24–28 in Prince Frederick rounds out fair season with agricultural exhibits, carnival rides and Southern Maryland cooking. Fall also brings art and river heritage to the county. Artsfest at Annmarie Sculpture Garden, Sept. 20–21 in Solomons will feature regional artists, food trucks and live music, while the Patuxent River Appreciation Day, Oct. 11 at the Calvert Marine Museum celebrates the bounty of the river with seafood vendors, exhibits and family entertainment.

From the excitement of the midway to the taste of fresh oysters and the rhythm of live music, fall in Southern Maryland offers something for everyone — a season that connects communities through food, tradition and celebration.