Discover None-of-a-Kind Gifts and Delights This Holiday Season in Leonardtown!

November 10, 2022

Town of Leonardtown invites you to discover the wonders of shopping small, shopping local this holiday season. If you’re looking for that one-of-a-kind, specialty gift to bring joy for the holidays, you’re sure to find it here. Spend the day discovering our local specialty stores. Our unique collection of galleries and shops are ready to help you with your holiday shopping.

The Town will also host popup shops, craft and vendor fairs and open houses and more featuring local artisans and crafters selling their hand-made treasures, and it all begins this weekend. Please mark your calendar and plan to join us for these special holiday events that feature amazing local vendors and artisans. We look forward to helping you fill your list with treasured items that are sure to delight.

Coastal Arts Holiday Market – Saturday, November 12th at Leonardtown Wharf from 9 a.m. – 3 p.m. An open-air marketplace at the Wharf. Shop from a wide variety of locally made and home-grown products.

The Holidays at Town Market – Saturdays from 9 a.m.- 6 p.m. and Sundays from 10 a.m. – 1 p.m. Shop Christmas Trees, wreaths, poinsettias, specialty gifts, organic, locally grown produce, baked goods, clothing, accessories, home décor, and more. Bring the family to enjoy holiday photos with the Grinch (special photo day for fur babies with the Grinch available on Saturday, December 10th at 10 a.m.).

Christmas on the Square and Annual Tree Lighting Ceremony – Friday, November 25th in Leonardtown Square from 4:30 p.m. – 8:30 p.m. In addition to rides, live music and entertainment, balloon art, holiday crafts, a live Nativity, pony rides, a petting zoo and more, this beloved annual event includes a Holiday Craft and Vendor Fair throughout historic downtown Leonardtown. Shop holiday decorations, specialty gifts and more. FREE shuttle rides are offered from CSM and the Governmental Center from 4:30 p.m. – 9 p.m.

Small Business Saturday  – Saturday, November 26th throughout Leonardtown from 1 p.m. – 5 p.m. Local businesses open their doors to help you fill your holiday list, and play host to Holiday Popup Shops from visiting businesses both inside and outside around the Square. Park and ride the Leonardtown Trolley for FREE from 1 p.m. – 5 p.m. to get around to all the great shopping around Town.

SOF Market Merchant Weekend Event – Sunday, November 27th at Shepherd’s Old Field Market, 11 a.m. – 5 p.m. Shepherd’s Old Field Market hosts its First Annual Holiday “Pop Out” vendor event with local visiting vendors outside and over 90 wonderful specialty shops indoors.

SOF Christmas Open House – Sunday, December 18th 11 a.m. – 5 p.m. shop from over 90 small businesses, enjoy refreshments, a gift-wrapping station and entertainment.