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 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 happening in November!
If you have an upcoming event, we would love to share it! Please enter your event details on our Events Calendar.
CALVERT COUNTY
Pink Friday: A Celebration of Small Businesses in Solomons on November 22 (12 pm to 8 pm), located at Solomons, MD – We’ll be sharing more details as the date approaches, but here’s what you can expect: Explore Solomons with our event map, guiding you through all the participating Pink Friday shops. Enjoy exclusive deals, support your favorite local businesses, and collect fun pink swag as you shop from spot to spot! Your final stop? Simply Social Event Co., where you’ll be decked out in pink for a fabulous photo op and a chance to win an exciting grand prize for visiting every location!
OLSS Christmas Bazaar on November 23 (9 am to 2 pm), located at Our Lady Star of the Sea School, 92 Alexander Ln, Solomons, MD – Join us at Our Lady Star of the Sea School for our annual Christmas Bazaar featuring vendors, Crafters, large indoor yard sale in Grannie’s Basement, Concession, Bakesale, Silent Auction and a special visit from Santa!
Annual Holiday Bazaar on November 23 (9 am to 3 pm), located at American Legion Stallings-Williams Post 206, 3330 Chesapeake Beach Rd, Chesapeake Beach, MD – Baked goods, kids craft table, Santa, raffles and vendors galore! Delicious lunch available.
Annual Christmas Bazaar & Crab Cake Dinner on November 23 (10 am to 5 pm), located at St. Paul’s Episcopal Church, 25 Church Street, Prince Frederick, MD – Pictures with Santa (10-noon, professional photographer, $20); Crab cake/Ham Dinner (noon to 5 pm, $30, or luncheon portions $20); Handmade crafts; Bake table; Attic treasures tag sale; and Raffle of gift baskets. What more could you ask? Free–Except for dinner and purchases.
“It’s Fall, Y’all!” Sip & Shop on November 23 (1 pm to 6 pm), located at Mully’s Brewery, 141 Schooner Lane, Ste 15, Prince Frederick, MD – Enjoy a pint of your favorite Mully’s brew and do some shopping from local vendors! The market will be open with plenty of products for you to peruse. And we’ve got food covered: everyone’s favorite Cousins Maine Lobster will be on site for all your lunch & dinner needs!
November Artisan Sip & Shop on November 24 (11 am to 5 pm), located at No Thyme to Cook, 14624 Solomons Island Road South, Solomons, MD – Our monthly artisan fair returns to NTTC! Local craftsmen and producers offer their wares at the artisan craft fair during this six-hour event. Wines, beers, and a wide array of other beverages will be for sale at the NTTC bar, together with seasonal food items. Sip & Shop takes place in NTTC’s parking lot, rain or shine. The craft fair is always free to enter.
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!
Rolling Acres Farm Christmas Weekend Spectacular taking place November 29 through December 1 (2 pm), located at 3305 St. Leonard Road, Port Republic, MD – Santa will be onsite along with a professional photographer (McIntosh Images) to take 3 digital images with access to online photo album. The fun doesn’t stop there. There are plenty other memories to be made. Shop for the perfect Christmas tree this holiday season, while having fun making holiday crafts, and enjoying a hot cocoa bar. Farm activities will also be available for additional fun. There will be a food truck onsite to enjoy brunch, dinner, and breakfast with Santa. We can’t wait to spend the holidays with you on the farm! $5 presale price for online sales. $7 at the gate.
Holiday Market on November 30 (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.
3rd Annual Kid’s Shopping Day on November 30 (10 am to 1 pm), located at Solomons Mission Center, 14454 Solomons Island Rd S, Solomons, MD – A special day for kiddos to shop for their siblings and loved ones! We even have some elves to help with wrapping! If you are interested in Volunteering, email Solomonsmissioncenter@gmail.com
Artist Market on November 30 (11 am to 4 pm), located at CalvART Gallery, 110 Solomons Island Road N, Prince Frederick, MD – Help us celebrate Small Business Saturday by coming out in support of our local artists! The Arts Council is hosting an Artist Market, where some of our member artists will have a booth setup in the gallery with items for sale. This is a wonderful opportunity to appreciate the artwork in our local community and show support for your local artisans who are sharing their talents. Come out and get a head start on some holiday shopping this year!
CHARLES COUNTY
Holiday Shoppe on Novermber 23 (9 am to 1 pm), located at La Plata United Methodist Church, 3 Port Tobacco Rd, La Plata, MD – Get your Christmas Shopping done at our annual Holiday Shoppe featuring original crafts and other exciting gift opportunities. Recycled Christmas decorations can be found and food will be available. Admission is free.
Winter Holiday Market on November 23 (10 am), located at Billingsley Community Center, 10069 Billingsley Rd, White Plains, MD – Enjoy shopping for unique crafts and handmade goods at our Winter Holiday Market. Just in time for those special holiday gifts! No need to bundle up, this event is held indoors! Free admission to shop, enjoy some hot cocoa, and find those special gifts!
Farmer’s Market on November 25 (1 pm to 5pm), located at The Master’s Child Church, 6485 Indian Head Hwy, Indian Head, MD – Experience the vibrant Farmer’s Market hosted at The Master’s Child Church on 6485 Indian Head Hwy in Indian Head, MD. Come and explore a variety of farm-fresh products, unique handicrafts, and delicious snacks in a welcoming and family-friendly environment. Embrace the spirit of community as you shop and connect with local vendors.
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.
ST. MARY’S COUNTY
Holiday Market with The Grinch & Cindy Lou Who on November 29 (9 am to 7 pm), located at Town Market, 22675 Washington St Leonardtown, MD – The Holiday Market will be open with all types of vendors to help get you started on your Holiday Shopping. Watch out for the Cindy Lou Who as she will be around making sure the Grinch doesn’t make any trouble. Get your pictures taken with The Grinch and Cindy Lou Who to take home. We will have the Race Cars and Classic Cars on display for everyone to see as well as a Light Display.
A Casual Christmas taking place 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!
Evening Tides: Candlelight Christmas at Piney Point Lighthouse on November 30 (5:30 pm to 7:30 pm), located at 44720 Lighthouse Road, Piney Point, MD – Join us for a festive holiday evening on the grounds of the beautiful historic park at Piney Point Lighthouse Museum featuring candlelight, carolers, hot chocolate bar, Buddy the Elf and the return of the annual Building Bricks Lighthouse Challenge competition (see below). Admission is free; a $5 per person donation is suggested. LOCAL GIFTS: Complete your holiday shopping for a wide range of of unique and local items inside our museum store while at the event. There is something for everyone on your list, including ornaments, art, kids’ items and much more. Can’t shop in-store? Shop on our online museum store: https://friendsmuseumstore.square.site/ MORE INFO: Call 301-475-4200 ext. 1832.
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