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 29, 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.

On Nov 30, 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 7, Summerseat Farm will host its annual Christmas Open House. 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 from 12-1p, the Chopticon High School band will perform.

Also on Dec 7, the University System of Maryland at Southern Maryland will host the Festival of Trees, showcasing festive trees and wreaths sponsored and decorated by generous supporters. In addition, visitors will enjoy an auction, DIY photos with Santa, food trucks, live music, raffles and kids' activities. Best of all: All proceeds benefit the local St. Mary's County Hospice community!

From Dec 7-8, the Lexington Park Business Association will host its annual Holly Days Extravaganza. On Dec 7, come for a Tree Lighting Ceremony from 6:30 – 7:30 p.m., with support from the Bay District Volunteer Fire Department. Then, on Dec 8 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, carolers from St. Maries Choral Arts, and display featuring the various holidays celebrated this time of year. All events take place in and around the Lexington Park Library.

From Dec 14-15, 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 and the world-famous Budweiser Clydesdales. Enjoy over 20 vendors, food trucks, raffles and bake sale.

On Dec 15, enjoy holiday music performed by Annie Moses Band at the Nancy R. and Norton T. Dodge Center for the Performing Arts. With signature arrangements of “God Rest Ye Merry Gentlemen,” “O Holy Night,” and sweeping originals like “When the Christmas Baby Cries," you will absolutely leave in the holiday spirit. Bring your whole family for a beautiful Christmas production!

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. Check out the Christmas Open House on December 7 from 9a-5p.
• 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. Check out their Black Friday and Small Business Saturday Special event on November 29 and 30. Check site for operating hours.

Winter Markets

On Nov 29 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 Dec 1 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 7 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 21 from 11a-4p, Dixon Family Farm will host their 2^nd 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.