SOUTHERN MARYLAND — The holiday season is just around the corner, and Southern Maryland is brimming with festive shopping events to help you find the perfect gifts while supporting local businesses. These December events are the perfect way to embrace the holiday spirit while discovering unique treasures and supporting your community. Here’s a roundup of local holiday shopping events you won’t want to miss!
If you have an upcoming event, we would love to share it! Please enter your event details on our Events Calendar.
CALVERT COUNTY
Black Friday & Small Business Weekend on November 29 and December 1 (10 am to 5 pm), located at Barefoot Wellness, 445 Main St, Prince Frederick, MD – Joining us this year, K’s Lunchbox & local vendors too!
Garden in Lights – Outdoor Holiday Light Show taking place November 29 through January 1 (5 pm to 9 pm – Closed some evenings, please check website for updated schedule), located at Annmarie Sculpture Garden & Arts Center, 13470 Dowell Road, Solomons, MD – A must-see holiday tradition for the entire family! Enjoy a stroll through the gardens to see the magical holiday lights display. In addition there will be holiday shopping, festive exhibits and food available for purchase at food trucks on-site. Advanced times-entry tickets are required for members and non-members! Check website for special nights and food truck schedule TBD. Closed on some evenings, please check website for updated schedule. This is a rain or shine event!
Museum Store Sunday on Sunday December 1 (10 am to 5 pm), located at Calvert Marine Museum, 14200 Solomons Island Road, Solomons, MD – Mark your calendars and shop with a purpose! The Museum Store is thrilled to participate in Museum Store Sunday, a global shopping event where you can find uniquely curated gifts while supporting our mission and fundraising efforts. On this special day, CMM members will draw for a chance to enjoy 25% – 40% off their entire purchase. One lucky member may even get their entire purchase for FREE! Non-members will receive a 20% discount all day. Some exclusions apply, see store for details.
Light Up the Town on December 1 (4 pm to 6 pm), located at Chesapeake Beach Town Hall, 8200 Bayside Road, Chesapeake Beach, MD – It’s TIMMMEE to light up this Town and get into the Holiday Spirit! Visit with Santa, shop local vendors, indulge in sweet treats & holiday activities, and enjoy a very special performance from Beach Elementary String Orchestra!
Artists Sunday Shopping @ Annmarie Garden on December 1 (10 am to 3 pm), located at Annmarie Sculpture Garden & Arts Center, 13470 Dowell Rd, Dowell, MD – Each shopper on Artists Sunday will enjoy complimentary tea or coffee, along with an Artsfest ’24 shopping bag (while supplies last). The Main Gallery at Annmarie has been transformed into a shopping wonderland! You’ll find thoughtful handmade gifts for everyone on your list, including ornaments, ceramics, jewelry, works of art, and more. Everything is made with love! Ornament Show & Sale, Holiday Gift Shop & Sale, Annmarie Gift Shop.
Joyful Paws Holiday Open House on December 1 (11 am to 3 pm), located at Calvert Animal Welfare League, 1040 Prince Frederick Blvd, Prince Frederick, MD – Adoptable pets, Bake Sale, Ask the Trainers, Thrift Shop, Vendors, Taste of the Tides Food Truck, Professional Pet Photos with Santa and more!
Home for the Holidays: Tree Lighting and Holiday Market on December 6 (4 pm to 8 pm), located at Downtown Prince Frederick Main Street and at the Courthouse – Holiday Market 4-8 p.m. on Main Street in Prince Frederick and tree lighting ceremony at 6 p.m. on the courthouse lawn. Enjoy supporting local vendors, food trucks, live music and more!
Holiday Market on December 7 (9 am to 2 pm), located at Cardinal Creek Plant Farm, 5180 Sixes Road, Prince Frederick, MD – Enjoy great seasonal shopping including over 30 vendors! Look for the perfect gift for that special someone and holiday decor for the home including holiday gifts, wreaths, greenery, candles art jewelry and much more! Admission to the market is FREE.
Daytime Holiday Market on December 7 (9 am to 2 pm), located at Annmarie Sculpture Garden & Arts Center, 13470 Dowell Rd, Dowell, MD – Outside, guests can browse a festive variety of market booths featuring gifts make with love. You will find unique jewelry, pottery, beauty products, home decor, small batch foods, and more. Everything is handmade, homemade, or homegrown with love. Inside the Arts Building, you will find live music, holiday exhibits, the Nature Nook – and more shopping in the Annmarie Gift Shop, the Holiday Gift Show, and the Ornament Show & Sale. There’ll be something for everyone on your list! Admission to the Market is FREE!
Christmas Town in Lusby on December 7 (10 am to 5 pm), located at East-John Youth Center, 11835 Mill Bridge Road, Lusby, MD – Holiday fun for the whole family! Santa, hayrides, vendors, music, food, silent auction, and more! Free admission. Call 443-985-2407 for more information.
ACLT Annual Wreath and Greens Sale on December 7 (11 am to 1 pm), located at American Chestnut Land Trust South Side Trailhead, 1985 Scientist’s Cliffs Road, Port Republic, MD – Stop by the southside trail head to purchase your holiday wreath, greens, and other goodies! Get there early as they sell out quickly!
An Old-Fashioned Christmas: Light Up Linden on December 7 (11 am to 4 pm), located at Linden House, 70 Church Street, Prince Frederick, MD – Join us for a FREE family day of holiday fun on the historic grounds of Linden, home to Calvert County’s Historical Society. You’ll find live music, activities for all ages, food trucks, vendors, a visit and reading with Santa and closing the day with a tree lighting!
Annual Holiday Market: Sip & Shop on December 8 (11 am to 4 pm), located at No Thyme to Cook, 14624 Solomons Island Road South, Solomons, MD – This festive afternoon has something for everyone – from a visit with jolly Santa to a mini craft fair featuring local artisans, and a gourmet hot cocoa bar. Admission is free but the memories are priceless!
Kids’ Christmas Shopping Event on December 13 (3 pm to 6 pm) and December 14 (10 am to 4 pm), located at Calvet Yards, 1921 Skinners Turn Rd, Owings, MD – Place for kids to purchase and wrap items for family members.
19th Annual Christmas Market on December 14 (10 am to 4 pm), located at All Saints Episcopal Church, 100 Lower Marlboro Road, Sunderland, MD – Expert craftsmen with sensational gifts for your holiday giving, homemade gourmet cocoa and Glühwein, music, home-baked goods, a silent auction and lunch make this Christmas Market the place to be! Visit 2 levels in the Parish Hall and outside. Bring your red, green or blue mug from previous years to buy beverage refills. Rain, snow or shine! Free admission & parking. Proceeds benefit parish & community projects.
CHARLES COUNTY
Mattawoman Creek Art Center’s Holiday Market taking place every Friday through Sunday until December 15 (11 am to 4 pm), located at Mattawoman Creek Art Center in Smallwood State Park, Smallwood State Park, 2759 Sweden Point Road, Marbury, MD – Get a jump start on your holiday shopping at the Mattawoman Creek Art Center’s 2024 Holiday Market in Marbury, Maryland’s beautiful, waterside Smallwood State Park. Expertly created handcrafts include ornaments, wooden tables, stained glass, knitted items, pottery, jewelry, photography, and many other unique artworks. The market is free. Park entry fees are waived for gallery visitors.
Small Business Saturday – La Plata MD on November 30 (Hours Vary by Location), located at Town of La Plata, La Plata, Maryland, 400 Charles St, La Plata, MD – Shop small and support your favorite local businesses — they’re your friends, your neighbors, your relatives, and some of the hardest-working people you know! La Plata’s downtown businesses are teaming up to celebrate the day together, with some special events sprinkled in. Plan on spending the day downtown — there’ll be plenty to eat, drink, and delight in. Participating businesses are listed here.
Sacred Heart Christmas Craft Fair on December 7 (9 am to 2 pm), located at Sacred Heart Parish, 201 Saint Marys Ave, La Plata, MD – Come and shop for homemade crafts, Christmas gifts, crocheted and knitted items, vintage items, local jewelry, aromatherapy oils and soaps and much more.
TC’s Christmas PopUp Shop on December 7 (11 am to 5 pm), located at 11800 Park Waldorf Lane, Suite 511, Waldorf, MD – Join Us for TC’s Cozy Corner Boutique Christmas Pop-Up Shop! Get ready for an amazing holiday shopping experience! On Saturday, December 7th from 11 AM – 5 PM, come and enjoy a festive day of shopping with our fantastic vendors, including Cozy Transportation Services, Tee Lover’s Cafe, Kelley’s Bags & Beauty, Park Lane Jewelry, and many more!
Kris Kringle Christmas Market taking place December 13 through December 15, located at Charles County Fairgrounds, 8440 Fairground Rd, La Plata, MD – This annual event offers light displays, holiday food, handmade crafts, children’s activities, shopping, music, and much more! This can’t miss event is a great way to celebrate this holiday season.
ST. MARY’S COUNTY
A Casual Christmas taking place on Fridays (6 pm to 9 pm), Saturdays (5 pm to 9 pm), and Sundays (1 pm to 4 pm) from November 29 to December 28, located at Mount Chance Farm, 23713 Mount Chance Farm Lane, Clements, MD – A Casual Christmas is a magical and unique Christmas experience sure to bring out the child in you. Our event takes place on a working farm in Clements, MD. Walk through our beautifully decorated equestrian barn where you can vote on your favorite stall, visit with friendly horses, shop from local vendors and artist and stop to see Santa. Just outside you will find face painting, hot chocolate, hay rides, pony rides, petting zoo, axe throwing, inflatables and more!
Holiday Open House at St. Clement’s Island Museum on December 1 (10 am to 5 pm), located at 38370 Point Breeze Road, Coltons Point, MD – Official opening of the Christmas Doll & Train Exhibit! The museum will offer fun for the entire family, including kids’ activities like face painting and make-a-toy workshop, music from COSMIC Flute Orchestra, and holiday refreshments including cookies and hot chocolate or mulled cider. Attendees can learn about Christmas in early colonial Maryland with Dr. Thomas Gerrard, St. Clement’s Island’s first landowner, run the model trains, see vintage dolls like Barbies and American Girls, and more! Get a jump on your holiday shopping with a wide variety of unique and local items inside the Museum Store. Admission is free for the day.
Holiday Open House at Piney Point Lighthouse Museum on December 1 (10 am to 5 pm), located at 44720 Lighthouse Road, Piney Point, MD – We’re kicking off the opening of the holiday season inside the museum and Keeper’s Quarters here at Piney Point Lighthouse with family activities, refreshments and more. This event is a special opening that encourages the public of all ages to come experience this unique Christmas setting in the museum. Free admission & refreshments available for all visitors. Get a jump on your holiday shopping inside the Museum Store, including the special edition 2024 museum ornament. For more info, call 301-994-1471.
Holiday Shopping @ The Belmont Farm on December 1 (10 am to 2 pm), located at 24079 Budds Creek Rd, Clements, MD – Save the date and join us for some festive shopping at The Belmont Farm for that special Christmas gift for that special person or a gift for yourself you deserve it! Come hungry, because Rita B Catering will be selling delicious stuffed ham and chicken salad sandwiches, yummy fried chicken dinners and the famous macaroni shrimp salad!! Also leave room for dessert because The Farmers Daughter will be selling some yummy goodies. Come support our local crafters and vendors!
Light Up Leonardtown First Friday on December 6, located at Town of Leonardtown – It’s First Friday Weekend in Leonardtown – explore, dine, and shop your way to a great time! You’ll find extra fun and special deals all around town.
Old Jail Museum First Friday in Leonardtown on December 6 (10 am to 7 pm), located at 41625 Court House Dr, Leonardtown, MD – Come take a tour of this fascinating historic site or shop at the Museum Store for a variety of unique gifts. Admission is free.
MBMS Holiday Bazaar on December 7 (9 am to 2 pm), located at Margaret Brent Middle School, 29675 Point Lookout Rd, Mechanicsville, MD – Santa and Mrs. Claus will be there for photos and we will have a kids activity table as well!!!! We have over 35 vendors that offer a variety of items so you are sure to find a gift for everyone and yourself!! There will also be indoor concessions and food trucks on site. Admission is FREE! We will be accepting monetary donations as all our proceeds directly benefit MBMS 6th grade students for school events such as quarterly incentives, school dances, and our end of the year celebration. We hope to see you there! Please reach out to Emma Ward at mbmsholidaybazaar@gmail.com if you have any questions.
5th Annual Winter Market on December 7 (10 am to 4 pm), located at Southern Trail Distillery, 27227 Morganza Turner Rd, Mechanicsville, MD – Come out and do some shopping with local vendors and artisans in preparation of the Holidays. Grab your favorite Southern Trail spirits (for you or for a gift), a delicious Southern Trail cocktail and listen to the one, the only Bradley Turner (12:00-3:00). This year the Chopticon Band will also be here playing Christmas Carols at 11:00 & 3:30. And the Grinch may make an appearance. Mark your calendars for a great time!!
Lexington Park Holly Days Extravaganza on December 8 (1 pm to 4 pm), located at St Mary’s County Library – Lexington Park Branch, 21677 FDR Blvd, Lexington Park, MD – Holly Days Extravaganza will be open to the public both in and around the library! This event will feature pictures with Santa, arts and crafts for all ages, a vendor shopping experience, carolers from St. Maries Choral Arts, and festive decorations!
6th Annual Holiday Open House @ Suttler Post Farm taking place December 14 through December 15, located at 38750 Chaptico Rd, Mechanicsville, MD – Spend a day on the farm with the gorgeous Suttler Post Clydesdales (they love to meet new pals!), 20+ vendors and food trucks. The Budweiser Clydesdales will also be at the farm both days! There will be plenty of raffle table items to grab a chance on, a 50/50 raffle, and a bake sale. The farm will be open for visitors Saturday, December 14th and Sunday, December 15th from 11am-4pm each day. Proceeds from the event benefit Hospice of St. Mary’s. Admission: $10.
Come Out and See the Grinch & Christmas Shopping Spree on December 14 (9 am), located at Town Market, 22675 Washington St, Leonardtown, MD – Come out and see the Grinch along with Max and Cindy Lou. Get your picture taken with the entire gang. Vendors are here to help you finish your Christmas shopping as well. Pictures with The Grinch are 10am to 4pm. Simply Q Barbecue will be here serving up some your favorites all day long.
2nd Annual GMHS Winter Bazaar on December 14 (11 am to 5 pm), located at Great Mills High School, 21130 Great Mills Rd, Great Mills, MD – We are holding the event on the same day as our Winter Festival of the Arts, so you can check off some items on your Christmas lists, see some magnificent art pieces, and listen to live festive music created by our talents fins arts students.
Last Chance Christmas Market on December 21 (11 am to 4 pm), located at Dixon Family Farm, 27075 S Sandgates Rd, Mechanicsville, MD – Bring the family and Christmas cheer to our 2nd annual Last Chance Christmas Market! Join us on the farm for last-minute shopping with our awesome local artisan vendors, craft beverage vendors, food trucks, fire pit, live music, and free photos with Santa! Weather permitting! Check our socials for last-minute updates.
Contact our news desk at news@thebaynet.com
