Holiday Spirit is Spreading Across St. Mary’s

As the holiday season approaches, our region transforms into a vibrant hub of festivities, holiday markets and signature events. So, bundle up, grab your loved ones, and embark on a holiday adventure in St. Mary’s County that you’ll cherish for years to come.

Here is our guide to the special events, markets and festivals that make St. Mary's County your holiday happy place.

Special Events

There are countless events that will brighten your holidays with all the small-town charm you expect in St. Mary’s County. Here is just a taste of events around the county, for a full list visit the Events Calendar.

On Nov 28, Leonardtown will host its annual Christmas on the Square in town center. For residents and visitors alike, the holiday season begins in Leonardtown when Santa arrives for the annual Christmas Tree Lighting. Fill your evening with holiday music, entertainment, horse and carriage rides, sleigh rides, train rides, hayrides, live nativity, petting zoo, face painting, children’s crafts, hot drinks, fresh kettle corn, and other fun activities! Stop by one of the downtown restaurants and shops around town while you are visiting.

Also on Nov 29, enjoy beautiful views of Piney Point Lighthouse Museum and Park during their Evening Tides: Candlelight Christmas event. Visitors will enjoy a festive holiday evening on the grounds of the historic park featuring candlelight, carolers, hot chocolate bar, Buddy the Elf, and the return of the annual Building Bricks Lighthouse Challenge competition.

On Dec 6, Historic St. Mary's city will host its Frost Fair! Between 1607 and 1814, the river Thames would freeze for months at a time. Beginning in 1607, there were seven total Frost Fairs held over the years when the Thames froze, allowing vendors to set up booths on the ice. HSMC is modernizing this idea with a holiday village featuring artisans, warm beverages, live music, and holiday light displays. Enjoy a day filled with family fun, live entertainment, and holiday cheer.

From Dec 6-7, the Lexington Park Business Association will host its annual Holly Days Extravaganza. On Dec 6, come for a Tree and Menorah Lighting Ceremony from 5:30 – 6:30 pm. Then, on Dec 7 from 1-4 p.m., a free Holly Days Extravaganza will feature pictures with Santa, arts and crafts for all ages, a vendor shopping experience, and display featuring the various holidays celebrated this time of year. All events take place in and around the Lexington Park Library.

On Dec 7, Summerseat Farm will host its annual Christmas on the Farm. The Manor House will be beautifully decorated for Christmas with freshly cut greenery and vintage decorations. Visitors will enjoy warm cider, cookies and Christmas music while touring the house. Believers of all ages will get a visit from Santa and can enjoy crafts, hayrides, visits with farm animals and tour the manor house.

On Dec 13, the Patuxent River Naval Air Museum will host their annual Holidays in the Hanger. Join for a magical day of holiday cheer among naval history, where there is something for everyone in the family. Find fun holiday crafts, sweet treats & hot cocoa, face painting and Santa Claus himself!

From Dec 13-14, Suttler Post Farm will host its Holiday Open House, raising money for the Hospice of St. Mary's. Visitors will spend their day on the farm with the gorgeous Suttler Post Clydesdales, who deliver The White House Christmas tree. Enjoy over 20 vendors, food trucks, wineries, raffles and bake sale.

On Dec 14, enjoy holiday music performed COSMIC Symphony and St. Maries Choral Arts at the Nancy R. and Norton T. Dodge Center for the Performing Arts. With the theme of "Gloria", there will be magical holiday surprises that are sure to be fun for the whole family during this free concert.

And that is not all! For a complete list of events, visit: Events Calendar | St. Mary's County MD Tourism

One Location, Countless Options

St. Mary’s County is home to countless small businesses, offering unique gifts to satisfy every need. Looking for a one-stop shop? Check out these single-space, multi-vendor shopping options.

• The Apple Basket: Over 6000 square feet of space with 13 uniquely themed rooms. Each room features gifts, jewelry, women's accessories, and home décor, all arranged among antiques.
• Cecil’s Country Store and Cecil’s Old Mill: Shop for unique Christmas gifts at the turn-of-the-century country store and adjacent old mill. Find antiques, collectibles, and artwork by local artists.
• Keepin’ It Local: This Southern Maryland boutique with a local focus offers a central market pantry filled with delicious local produce, meats, cheeses, and a variety of baked goods. Keepin' It Local specializes in unique gifts and art that you will not find elsewhere. The surrounding area is also filled with a variety of local artist vendors to browse and shop.
• Shepherd's Old Field Market: Whether you are looking for that unique home décor item or special gift or just feel like spending an afternoon wandering through over 90 shops and services, Shepherd's Old Field Market has something for everyone and there's always something new!
• The Vintage Source: From a former general store to an abundance of refinished furniture, the shop comes alive with hundreds of people buying refinished furniture including dressers, mantles, slip covered wing chairs, vintage jewelry, metal furniture, gilded mirrors and architectural pieces to update your homes.

Free Winter Markets

On Nov 28 from 9a-7p, visit the Holiday Market at Town Market, hosting various vendors to aid in your holiday shopping. Bring the whole family, unless you are buying for them, to meet Cindy Lou Who; she is keeping an eye out for the Grinch to make sure he doesn’t make any trouble. In addition, there will be race and classic cars on display and a holiday light display. Trabakes and Lauren's Lumpia will be serving food and kids can enjoy a special holiday craft table.

On Nov 30 from 10a-2p, enjoy Holiday Shopping at the Belmont Farm ahead of the holiday season. Rita B Catering will offer up their stuffed ham, chicken salad sandwiches, fried chicken dinners, and famous macaroni shrimp salad. The Farmers Daughter will be selling yummy goodies for dessert. 

On Dec 6 from 10a-4p, Southern Trail Distillery will host their Winter Market, featuring local vendors and artisans. Grab your favorite Southern Trail spirits (for you or as a gift), a delicious Southern Trail cocktail, and listen to the one and only Bradley Turner from 12pm-3pm or the Chopticon High School Band playing Christmas Carols at 11:00am and 3:30pm.

On Dec 20 from 11a-4p, Dixon Family Farm will host their 3r^d annual Last Chance Christmas Market. With more than 70 local vendors signed up, customers will have a chance to finish their holiday shopping with a bang! During your visit, enjoy food trucks, free pictures with Santa, live music and more.

Start planning your getaway in St. Mary’s County!

Whether you're visiting St. Mary's County as your annual holiday getaway or preparing to entertain family from out of town, we have all of the recourses you need to plan an unforgettable holiday season. Find a hotel, BnB, Inn or vacation rentals that fits your needs and makes you feel at home during this holiday season.