Christmas on the Square & Annual Tree Lighting

Schedule

Fri Nov 27 2026 at 04:30 pm to 08:30 pm

UTC-05:00
Location

Town of Leonardtown | Leonardtown, MD

Advertisement
The holiday season begins in Leonardtown when Santa arrives for the annual Christmas Tree Lighting in the Town Square. The festivities begin at 4:30 PM with 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! Many downtown restaurants and shops around the Town Square will be open and decorated for your holiday pleasure.
Visit https://www.visitleonardtownmd.com/christmasonthesquare for more details.
Advertisement

Where is it happening?

Town of Leonardtown, 22697 Washington St, Leonardtown, MD 20650-3848, United States

Event Location & Nearby Stays:

Know what’s Happening Next — before everyone else does.
Town of Leonardtown
Host or PublisherTown of Leonardtown

Tags

Christmas in LeonardtownKids in LeonardtownHoliday in LeonardtownArt in LeonardtownChristmas-lights in Leonardtown

Ask AI if this event suits you

Keep exploring

Discover more events in Leonardtown

More concerts, festivals, nightlife and things to do happening near you.

Sat, 28 Nov at 09:00 am Small Business Saturday with The Grinch & Cindy Lou Who

Town Market LLC

DANCE ENTERTAINMENT
Sat, 05 Dec at 09:00 am Fur Babies with the Grinch and Holiday Market

22675 Washington St, The Bell Bldg Unit 106, Leonardtown MD

CHRISTMAS-MARKETS-AND-FAIRS HOLIDAY
Sat, 05 Dec at 04:00 pm Home for The Holidays - A New St. Mary's County Holiday Tradition

Saint Mary's Fairgrounds

FITNESS KIDS
Sat, 12 Dec at 09:00 am Come Out and See the Grinch & Christmas Shopping Spree

Town Market LLC

CHRISTMAS SHOPPING
Sat, 12 Dec at 09:00 am BAF Holiday Dressage Schooling Show

41345 Camp Maria Rd, Leonardtown, MD 20650-4220, United States, Leonardtown, MD

HOLIDAY CALENDAR
Sun, 13 Dec at 11:00 am Photos with Santa! (Pet **all species** and kid friendly)w

Balanced Paws Pet Care

NONPROFIT
Fri, 27 Nov at 10:00 am Holiday Market with The Grinch & Cindy Lou Who

Town Market LLC

CHRISTMAS-MARKETS-AND-FAIRS HOLIDAY
Fri, 27 Nov at 11:00 am Letters to Santa

22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD, United States, Maryland 20650

Fri, 27 Nov at 04:30 pm Christmas on the Square & Annual Tree Lighting

Town of Leonardtown

HOLIDAY ART
Sat, 28 Nov at 09:00 am Small Business Saturday with The Grinch & Cindy Lou Who

Town Market LLC

DANCE ENTERTAINMENT
Sat, 05 Dec at 09:00 am Fur Babies with the Grinch and Holiday Market

22675 Washington St, The Bell Bldg Unit 106, Leonardtown MD

CHRISTMAS-MARKETS-AND-FAIRS HOLIDAY
Sat, 05 Dec at 04:00 pm Home for The Holidays - A New St. Mary's County Holiday Tradition

Saint Mary's Fairgrounds

FITNESS KIDS
Sat, 12 Dec at 09:00 am Come Out and See the Grinch & Christmas Shopping Spree

Town Market LLC

CHRISTMAS SHOPPING
Sat, 19 Dec at 10:00 am Pictures with Santa Clause

Town Market LLC

PICTURES-WITH-SANTA SHOPPING

What's Happening Next in Leonardtown?

Discover Leonardtown Events