APRIL 2, 2022

It was a wonderful evening of creativity and fun at the Plein Air at the Wharf Event. Artists captured the beauty of Breton Bay using a variety of medium while enjoying smooth jazz performed by the GrooveSpan Trio and sampling award-winning wine from the Port of Leonardtown Winery and tasty eats from Farm.Fork.Soul and Linda’s Café on the Go and sweet treats from the Frog Town Ice Cream Shop. 

OCTOBER 2, 2021

It was a great day at the 2021 Bruderfest at the Brudergarten Beer Garden at Shepherd’s Old Field Market. The day's festivities kicked off with a Pet Costume Contest followed by Duschound Races, It was an exciting start to an amazing event!

OCTOBER 2, 2021

Cruisin' Southern Maryland for Vets made a quick stopover in Leonardtown on Saturday, October 2, 2021 and filled the Town with an exciting mix of modern hot rods and classic antique cars. This worthy annual event raises money for local Southern Maryland Veterans. 

OCTOBER 23, 2021

There was beautiful weather, amazing costumes (We saw superheroes, witches, dinosaurs, larger than life characters, an airplane, rockets and a mad hatter too!), delicious food and yummy treats, spooktacular decorations and was that a baby goat in the pet costume contest!?! What an thrilling day in Leonardtown!

OCTOBER 2, 2021

The festivities continued at the 2021 Bruderfest with His and Her Stein Lifting Contests and live music from HydraFX who electrified the audience with their unique fusion of Rock, R&B & Reggae music! It was a memorable day of fun and merriment!

JULY 9 & 11, 2021

The Potomac Jazz & Seafood Festival Weekend Celebration in Leonardtown, 
held on Friday, July 9 - 11, 2021 was filled with exciting events and happenings throughout Leonardtown and St. Clements including jazz brunches, art shows, a flapper-style barre class, jazz cruises, live music throughout Leonardtown and more!

OCTOBER 9, 2021

Families gathered in Leonardtown Square in spite of the intermittent rain to enjoy the Annual Antique Power and Tractor Parade on Sunday, October 10, 2021. This great event helped tor raise funding for Christmas in April St. Mary's County, Inc., an organization that helps rehabilitate the homes of low-income homeowners, particularly the elderly and individuals with disabilities.

SEPTEMBER 3, 2021

Arts & Entertainment First Friday is an annual event that celebrates Leonardtown's designation as an Arts & Entertainment District. This year's festivities, held on Friday, September 3, 2021 included community art projects, plein air painting demonstrations, live music, dancing and more! Photo by the Town of Leonardtown

JUNE - OCTOBER 2021

Leonardtown hosts a summer of exciting concerts featuring the SOMD Storytellers,
Robbie Boothe, Phillip Michael Parsons, Latrice Carr, Sam Grow, the Amish Outlaws and more throughout the Town of Leonardtown, Maryland from June - October 2021. Join us for an exciting Summer of Music and Fun!