Shop Local, Southern Maryland

Hometown Heart Apparel

Hometown Heart Apparel has the coolest locally designed apparel… t-shirts, sweatshirts, hats, kids’ clothes, and onesies. Hometown Heart Apparel, a local woman-owned company, began as a way to celebrate our hometown, St. Mary’s County as well as Southern Maryland. You can purchase your Hometown Heart Apparel online as well as at SPICE Studio in the Leonardtown Square. 

Port of Leonardtown Winery

Give the gift of Gold medal-winning local wine this holiday season! Port of Leonardtown Winery, is won top honor trophies and multiple gold medals this year.  Open seven days a week, offering a wide variety of wine styles ranging from sweet and fruity, to bold and dry. Prices range from $13-$45 per bottle. Also offering private events, Wine Club memberships, and lots of fun gift ideas. Check Facebook @portofltownwine for the latest live music and event details.

23190 Newtowne Neck Rd, Leonardtown, MD 20650

Natural Looks by Victoria

Gift certificates available for lash extensions: $100 for the initial application for new clients ($25 savings) or lash packages at $355 for initial application PLUS 4 fillers ($85 savings). Gift Certificates are also available for one-on-one Makeup Made Simple classes. The owner is Victoria Ronan, Certified Make-Up Artist & Certified Lash Extension Specialist located at Barefoot Wellness 445 Main Street, Prince Frederick.

Boudoir By Beth

Searching for a gift for the man, or woman, who has everything? Boudoir by Beth may have just what you are looking for – if you dare. The “little black book” leather album consists of 20 boudoir photographs with a dream print coating on museum archival quality paper. Photo sessions are priced at $350. This fee includes professional hair styling and make-up application by a highly talented beauty team, wardrobe add-ons, beverage and treats. The sessions can be either at the studio or on-location in your home. Photos purchased separately.

22760 Washington Street, Unit 1, Leonardtown, MD 20650

Finer Sweets

Craving a handcrafted and classic apple pie made to order? Well now, this can be delivered to your doorstep by local bakery Finer Sweets. Finer Sweets offers cookies & cupcakes, custom cakes, treat boxes, and their seasonal Apple Pie for $25. Order online! Vegan option available! Delivery is available in St. Mary’s, Calvert, and Charles Counties. Order via phone, email, or online. Proud to be a woman and veteran-owned business.
[email protected] 

Get Festive: Nov/Dec Events & Activities

Annual Christmas Tree Lighting in the Leonardtown Square

The holiday season officially begins when Santa arrives for the annual Christmas Tree Lighting in the Town Square. This year’s festivities include 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 korn, and other fun activities!

  • Admission: Free
  • Date/Time: Nov. 26, 4:30 p.m. – 10 p.m.
  • Location: Leonardtown Square, Leonardtown, MD

Elf, The Musical

Enjoy a live performance of Elf, The Musical by The Newtowne Players for the holiday season! If you enjoyed the movie, you are sure to enjoy this musical. This modern-day holiday classic is sure to make everyone embrace their inner elf.

  • Admission: Adults $18; seniors/students/military $15; children $13; Thursdays $13 all day.
  • Dates/Times: Nov. 12 – Dec. 12;Thursday – Saturdays at 8 p.m., and Sundays at 3:30 p.m.
  • Location: The Newtowne Players Theater, Lexington Park MD

Christmas at Flat Iron Farm

Come kick off the holiday season right in St. Mary’s County! Come visit Flat Iron Farm for fun holiday activities, say hi to Santa, hayrides and pony rides, a petting zoo, crafts, hot cocoa, holiday shopping, and much more!

  • Admission: Free
  • Dates/Times: Nov. 24 – Dec. 24, evenings
  • Location: Flat Iron Farm, Great Mills, MD

Piney Point Lighthouse Museum Holiday Exhibit

Come enjoy guided tours during the holiday season at Piney Point Lighthouse Museum & Historic Park. We’re proud to unveil our BRAND-NEW exhibits inside the museum (and maybe a little holiday decorating at the lighthouse and keeper’s quarters!).

Southern Trail Holiday Market

Kick-off the holiday season with this holiday market at Southern Trail Distillery! This holiday market will feature local vendors, giving you the perfect opportunity to start or finish your holiday shopping. Keep warm with handcrafted beverages from this family-owned distillery and even find the perfect stocking stuffer with handmade flavored moonshine.

  • Admission: $7 adults and $3.50 for senior citizens, military personnel, and students
  • Date/Times: Nov. 28 – Jan. 2; 12 – 4 p.m. daily.
  • Location: Piney Point Lighthouse Museum and Historic Park, Piney Point MD
  • Admission: Free
  • Date/Time: Dec. 4, 10 a.m. – 4 p.m.
  • Location: Southern Trail Distillery, Mechanicsville, MD

St. Clement’s Island Museum Christmas Doll & Train Exhibit

Enjoy a holiday exhibit of antique and collectible dolls (like Barbie, American Girl and more), classic trains and other retro toys in this festive holiday display inside the museum.

  • Admission: $3 Adults; $2 seniors and military; $1.50 children; 5 and under are free.
  • Date/Time: Dec. 1 – Jan. 2; 12 – 4 p.m. daily.
  • Location: St. Clement’s Island Museum, Colton’s Point MD

Northern High School Holiday Craft Fair

Check out more than 80 expert crafters and vendors. Door Prizes! Santa Claus! Santa’s Workshop for kids! All money raised at this event goes directly to the band program.

  • Admission: Free; donations welcomed.
  • Date/Time: Dec. 11 from 9 a.m. -3 p.m.
  • Location: Northern High School, Owings, MD


Enjoy an assortment of craft beer while listening to a local band (Flippin’ Eyelids), perusing items from artisan vendors, and playing lawn games. Food appealing to all taste buds will be available for purchase from food trucks. Wine will also be available for purchase.

  • Admission: VIP drinkers: $30 in advance, $35 at the door; general admission: $20 in advance; $25 at the door; designated drivers & non-beer drinkers: $10
  • Date/Time: Nov. 13 from 1 – 5 p.m.
  • Location: Historic Sotterley, Hollywood, MD

Humane Society of Charles County Annual Holiday Craft Fair

The best crafters in Southern Maryland will have terrific items just in time for your holiday shopping.

Raffles of donated craft items throughout the day.

  • Admission: Free
  • Date/Time: Dec. 5 from 10 a.m. – 3 p.m.
  • Location: Thomas Stone High School, Waldorf MD

Kris Kringle Christmas Market

Modeled after the famous markets in Germany, this annual event at the fairgrounds offers light displays, holiday food, handmade crafts from local artists and crafters, children’s activities, shopping, music, and much more. Activities will include Santa’s arrival, Christmas tree lighting, Strolling Carolers, music from local school choruses and bands, an array of sales by local non-profit groups such as the Boy Scouts, children’s activities run by the 4H club, a lighted holiday path and Christmas Village. This year, we will again be having winter fireworks!

  • Admission: $3
  • Dates/Times: Dec. 10, 4- 8 p.m.; Dec. 11, 9 a.m. – 8 p.m.; Dec. 12, 10 a.m. – 3 p.m.
  • Location: Charles County Fairgrounds, La Plata, MD

Garden in Lights

Annmarie Garden In Lights will transport you and your family to an enchanted world full of glowing “light sculptures” and wondrous light installations. Discover magical creatures, wintery wonderlands, musical holiday scenes, deep-sea treasures, sparkling trees, and so much more! You’ll find sparkling delights and fun photo ops around each corner!

  • Admission: Tickets on sale soon
  • Dates/Times: Nov. 26 - Jan. 1, 5 – 9 p.m.
  • Location: Annmarie Sculpture Garden & Arts Center, Lusby, MD
Photo by Annmarie Gardens

Solomons Christmas Walk and Boat Parade

Enjoy Solomons’ annual Christmas walk and a lighted boat parade. Explore the shops in downtown Solomons, listen to music, indulge at restaurants, and watch the boat parade at dark from anywhere on the island.

  • Admission: Free
  • Dates/Times: Dec. 4, 5 – 9 p.m.
  • Location: Solomons Island, MD