Holiday Fun

Make merry in St. Mary's!

Catch the glow! St. Mary's is filled with warmth and holiday cheer. Make merry at festivals and feasts throughout the season.

Making Merry

St. Mary's County is full of holiday events. Make merry by the glow of candles at our historic houses or light up with smiles at outdoor light displays. Learn more

Historic Leonardtown

Historic Leonardtown brims with holiday cheer. There's a tree in the old-fashioned town square, decorations in store windows and a host of holiday happenings for couples and families to enjoy. Learn more

Dining

Winter is time for oysters and seafood from the Bay! Pair them with amazing local wines at many of our restaurants. Experience colorful joyful Madrigal Dinners at Maryland's first capital, Historic St. May's City. Learn more

Shopping

Gift shopping is fun when the stores are as unique as their wares. Old post offices and country stores along our byways have found new life as antique shops while Leonardtown is a great place for art. Learn more

Tasting

If your passion is discovering great wines and sharing them with your friends, then St. Mary's is worth the visit. Sip and savor at our wineries and delight in some great finds.

Port of Leonardtown WinerySlack Winery

Romancing

Cozy inns and bed and breakfasts with water views offer great getaways for two. Or rent a beachfront house and gather the far-flung family for a holiday to remember. Learn more