Where To Shop, Play & Give Local This Holiday Season In Southern Maryland

Action Jaxx Indoor Playground

Annmarie Sculpture Garden & Arts Center Holiday Shopping

The Main Gallery at Annmarie Garden has been transformed into a holiday shopping wonderland! It’s filled with artful finds and Christmas trees decorated with handmade ornaments from local artists. Grab a basket and shop right off the trees! Annmarie Garden in Lights is also hosting several outdoor nighttime Christmas Markets, all of which is part of the Annmarie Garden in Lights experience.

There will also be two Daytime Holiday Markets (December 6 and 13), with free admission. These markets feature over 60 regional artists and vendors, food trucks, and holiday shopping in the Main Gallery.

Address: 13470 Dowell Road, Solomons, MD
Phone: (410) 326-4640

Cecil’s Country Store

Cecil’s Country Store is a Southern Maryland landmark known for its warm, hometown charm and welcoming atmosphere. It brings together the region’s best antiques, unique gifts, and locally inspired treasures all under one roof. As a community favorite, it blends history, quality, and friendly service to create a one-of-a-kind shopping experience.

Address: 20853 Indian Bridge Rd., California, MD
Phone: (301) 994-9622

Charles County, With Love From Charles, Gift Cards

Charles County’s digital gift card program, With Love From Charles, is a simple and easy way to show love to local businesses. Gift cards are redeemable at more than 40 participating Charles County businesses.

Buy One Get One now through Dec. 23, 2025.
When you purchase a $25, $50, $75, $100 or $150 value gift card, you will receive a bonus card matching the same value. For example, if you buy a $50 card, you get a bonus $50 card for free. Learn more here.

Dees Mutts Dog Grooming

Pamper your pet this holiday season with a grooming experience they’ll love. Dees Mutts offers full-service grooming, bathing, and cage-free care to keep your furry family members looking and feeling their best. Gift certificates are available — a perfect stocking stuffer for any pet parent.

Address: 2896 Old Washington Rd., Waldorf, MD
Phone: (301) 752-9472

Devils Den Escape Rooms

The Devils Den Escape Rooms experience in Mechanicsville 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, our three expertly designed rooms will test your problem-solving skills and challenge you to think creatively in a high-pressure, adrenaline-fueled environment.

Address: 29190 Three Notch Road, Mechanicsville, MD
Phone: 301-885-8429

Genna Ross Elite Fitness & The Space Collective

Genna Ross Elite Fitness and The Space Collective LLC are a women-centered wellness and movement hub located inside Gym 24/7 in Prince Frederick. Founded by certified master trainer and Pilates instructor Genna Ross, the space blends strength training, Pilates, mindset work, and personalized coaching in a supportive, empowering environment designed to help women build confidence, strength, and community.

Take a class for FREE and tour the facility. Free Workout Wednesdays every week!

Address: 2192 Solomons Island Rd. S, Prince Frederick, MD
Phone: (240) 298-3648
Email: styledbygenna@gmail.com

Heritage Chocolates

Experience the magic of the holidays with Heritage Chocolates, where every artisan piece is crafted in small batches for unforgettable flavor. Their curated holiday collections and beautifully packaged gift boxes make the perfect treat for family, friends, coworkers, or clients. Celebrate the season with locally made sweetness — and support a treasured Southern Maryland small business.

Address: 22795 Washington Street, Leonardtown, MD 20650
Phone: (240) 587-3123

Keepin’ It Local

Keepin’ It Local, the building that was once considered a “tear down,” is now a beautifully restored structure that serves as a destination spot for locals and visitors to meet, shop, and enjoy the creations of Southern Maryland artists, crafters, and growers. It’s a unique, community-focused boutique filled with handmade goods, local talent, and one-of-a-kind finds. A perfect stop for thoughtful, local holiday gifts this season.

Address: 25760 Colton Point Road, Morganza, MD
Phone: (240) 526-3910

Mandy Lee’s Vintage Shop & Studio

Discover one of Calvert County’s best-kept secrets this holiday season at Mandy Lee’s Vintage Shop & Studio — a charming destination for fine art, antiques, salvaged pieces, artisan creations, and one-of-a-kind finds. From art classes to community events and beautifully curated vintage décor, there’s something special for every shopper. Gift cards are available, making it the perfect stop for unique, thoughtful stocking stuffers.

Address: 136 Main Street, Prince Frederick, MD
Phone: (410) 991-5988

Scary Strokes

Scary Strokes, Southern Maryland’s premier destination for family FUN! Featuring a one-of-a-kind indoor 18-hole blacklight miniature golf course, 40 state-of-the-art arcade games, a full-motion 360-degree virtual reality esports Omni Arena, and the Graveyard Grill. Perfect for friends, families, or that special date night — they truly have something fun and exciting for everyone!

Address: 2960 Technology Place Suite 106, Waldorf, MD
Phone: (301) 705-7000

Southern Maryland Paintball

Give the gift of adventure this holiday season — and keep the excitement going long after the celebrations end. Southern Maryland Paintball offers fun for the whole family (ages 4–104!) with Gellyball, low-impact and traditional paintball, axe-throwing, mobile axe trailers, and unforgettable birthday or team events. Gift certifictes make the perfect stocking stuffer for kids, teens, and adults.

Address: 11272 Edge Hill Rd., Newburg, MD 20664
Phone: (240) 419-9626