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 27, 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 some of the downtown restaurants and shops around town while you are visiting.

From Nov 29 to Jan 3, enjoy beautiful views of Piney Point Lighthouse Museum and Park during Holidays at Piney Point. Come enjoy guided tours for all ages, with the Keeper’s Quarters and museum decorated for the holidays, and see the special festive exhibits. Stop by on Nov 28 for Christmas at Piney Point, their holiday opening day! Find Christmas lights galore, 18 themed Christmas trees, an 18-foot Crab Pot Christmas tree, s'mores pit, a few craft vendors, carolers, Santa & Mrs. Clause, Frosty the Snowman, Storytime with Buddy the Elf, the Lighthouse Keeper's scavenger hunt, and the return of the 3rd Annual LEGO Lighthouse Building Challenge.

Starting on Dec 4, check out the unique and custom gingerbread people all throughout Leonardtown for Gingerbread Lane! Businesses and families throughout the county decorate a "Gingey" and you can vote for your favorites through Dec 20.

On Dec 5, the Lexington Park Business Association will host its annual Holly Days Extravaganza. Come for a Tree and Menorah Lighting Ceremony in the evening at the Bay District Fire House. Activities during the day 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. Daytime activities take place in the Lexington Park Library and at the Bay District Fire House.

New for this year also on Dec 5 is Wrapped Up in Local: a Holiday Pop-Up Shop! Think Hallmark Christmas movie meets your childhood school holiday shop, featuring a thoughtfully curated collection of gifts from local businesses, artists, makers, wineries, and a brewery. Purchase a bottle of wine or a growler and receive a FREE gift box for your goodies! There will also be a dedicated gift-boxing station where you can put together a thoughtful, personalized gift, ready to go under the tree.

On Dec 12, 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 12-13, 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 13, COSMIC Symphony’s Winter Concert, titled "Do You Want to Build a Snowman?" will be filled with magical holiday surprises that are sure to be fun for the whole family. COSMIC is pleased to present this concert free of charge.

On Dec 19, 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!

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.

Free Winter Markets

While it's open year-round, The Barns at New Market begins its holiday season on Nov 14 until Dec 19. Shop the indoor and outdoor vendors offering a wonderful selection of local agricultural products, freshly baked goods, honey, meats, handmade items, and so much more. Get a head start on your holiday shopping while supporting our local farmers, producers, and small businesses.

On Nov 27 from 10a-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. Try a selection of baked good and coffee while the kids can enjoy a special holiday craft table.

On Nov 28 from 10a-3p, check out the Potomac Gardens new holiday event: the Beers and Bargains Christmas Market! Shop vintage items, antiques, handmade items and local finds. Sip & shop around.

On Nov 29 from 10a-2p, enjoy Holiday Shopping at the Belmont Farm ahead of the holiday season. Grab your friends and join for a day filled with great shopping, delicious food, and festive fun. Rita B Catering will offer up their stuffed ham, chicken salad sandwiches, fried chicken dinners, and famous macaroni shrimp salad.

On Dec 5 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 Nightcap Trio from 12pm-3pm.

Also on Dec 5 from 11a-6p, it's the most wonderful time of the year at Barefoot Farms Christmas Market. Join for a magical day on the farm filled with holiday cheer, unique gifts, delicious food, music, and festive fun for the whole family! 

On Dec 6 from 12p-5p, enjoy a special, indoor edition of Analog: Pop Up Market at The Rex. Find a curated list of vendors bringing everything from skate gear, artwork, books, to vinyl records and other forms of physical media. Analog is all about community - supporting small sellers, connective, creatives, and giving people a laid-back space to explore, talk, and discover something unexpected.

On Dec 19 from 11a-4p, Dixon Family Farm will host their annual Last Chance Christmas Market. With many 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.

Vintage Shopping:

• The Apple Basket: Over 6,000 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.
• 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.
• The Vintage Collective: A vintage, multi-vendor store featuring thoughtfully curated clothing, accessories, collectibles, home décor, furniture, and a variety of unique hard-to-find gems in Leonardtown.
• Rust & Grain: Explore over 4,000 square feet at this vintage market, offering a huge selection of custom and vintage furniture, housewares, decor, and other unique goods. They also offer custom refinishing services, where a talented artisan will give a fresh look too old or outdated furniture.

Unique Finds:

• 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!
• Marie and Nash: Family-owned one-stop shop for all things beautiful, small batch, artist-made, and sustainable. Find items from all over the world and from Southern Maryland.
• Fenwick Street Used Books and Music: Quaint book shop located in historic downtown Leonardtown in what used to be Duke's Bar, a town landmark. Just off the main square, the bookstore holds over 27,000 books, as well as all kinds of vinyl records, including a plethora of collectible rock, jazz, blues and big band albums.
• The Chandlery at Pier450: The name derives from a ship’s chandlery, historically a source of marine supplies for sailing ships. This Chandlery is a sundry store for boaters with a little something extra — a retail boutique of unique finds, beautiful items and eclectic fashions, from art and home décor to jewelry and clothes, plus edibles, health & beauty aides and toys.
• North End Gallery:  The oldest art gallery in St. Mary's County offers a diverse collection of original fine art, jewelry, and crafts by as many as 35 juried artists and artisans from Southern Maryland. Shows featuring gallery artists change monthly with ongoing availability of works by all the gallery artists.
• Meow Dyer Cat Cafe: A place where every cat lover can find their purr-fect spot! This cozy space is designed for you to relax and enjoy the company of their adorable feline friends. Join for a kitty-riffic experience that celebrates all things cat.

Sweet Treats:

• Heritage Chocolates: Heritage Chocolates was established in 2015 and has brought handmade chocolates and confections to Southern Maryland, aiming to provide quality products that customers know and love, while continuing to develop exciting, new flavors. Today, the kitchen produces over 75 unique recipes.
• Black Point Chocolatiers: Black Point Chocolatier is dedicated to crafting Southern Maryland's finest handmade chocolate. Located within Blue Wind Gourmet Lexington Park, they specialize in hand making the finest chocolates using only the best sourced ingredients.
• McKay's Grapes, Grains & Gatherings: This store brings together carefully selected wines, spirits, local craft beverages, gourmet foods, and thoughtful gifts designed for celebrations, gatherings, and everyday moments.

Gift Cards for Experiences:

• Above Par Golf & Entertainment: Above Par Golf provides golf services and entertainment to the community and visitors. They focus on bringing the fun side of golf to the forefront of the game and want others to experience and enjoy golf as a past time. Their site includes: virtual simulators, youth and adult instruction, putting green, event hosting, and golf merchandise.
• Devil's Den Escape Room: This escape room experience is the ultimate challenge for thrill-seekers, puzzle enthusiasts, and anyone who loves a good challenge. Whether you are a seasoned escape room enthusiast or a first-time adventurer, the expertly designed rooms will test your problem-solving skills and challenge you to think creatively in a high-pressure, adrenaline-fueled environment.
• Viking Axe Throwing: Channel your inner Viking and master the art of axe throwing at Viking Axe Throwing and Rentals. You'll learn how to safely and properly throw axes, ninja stars, and other weapons. Once you get your first bullseye, you'll be hooked!
• SMASHRx: Discover your ultimate stress relief at SMASHRx, a local rage room dedicated to helping you manage everyday pressures and enhance your mental well-being. Unleash your emotions in a safe and supportive environment. Locally owned and operated, they are proud to bring Southern Maryland a one-of-a-kind destination where stress relief and entertainment collide.
• Maryland International Raceway: The largest motorsports facility in Maryland features over 100 events annually from March through November and seats 11,000 fans. See the most exciting machines in drag racing, Pro Stocks, Pro Mods, Funny Cars, Jet Cars, and more. Plus, MDIR hosts the best sportsman races and programs in the country. Treat yourself to an awesome race experience that is bound to be a blast for the entire family.

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 or short-term rental that fits your needs and makes you feel at home during this holiday season.