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leonardtown first fridays

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Join us year-round every First Friday of the month when historic Leonardtown's art galleries, restaurants, cafés, gift shops, antique shops, bookstores, etc. open their doors to showcase local artists and/or serve specials at their establishments. Starting with the month of May each year, Leonardtown First Fridays are extended to Leonardtown First Friday All Weekend Events and continue through October. See the upcoming event themes below!

First Friday All Weekend Event Themes:

Cinco de Mayo


Cinco de Mayo First Friday
May 5 - 7, 2023

Enjoy live music, make & take art activities, a
Cinco de Mayo Art Show, Bilingual Story Time, face painting featuring Día de los Muertos designs, Children's Merengue Dance Lessons, live Mariachi music, a live Lucha Libre event, specialty food and much more Friday, May 5th - Sunday, May 7th
(times vary)!

Download the First Friday Weekend Itinerary

Friends at Art Store


Art Walk/A&E First Friday
September 1 - 3, 2023

Leonardtown celebrates the anniversary of its designation as an Arts & Entertainment District (it's the only one in Southern Maryland) with Art Walk A&E First Friday. Enjoy live music, art vendors, an outdoor movie, performances and more throughout the weekend, and vote on your favorite art pieces displayed in local businesses.

Outdoor Barbecue


Grillin' & Chillin'
First Friday
June 2 - 4, 2023

Gather your family and friends for an old-fashioned summertime fun in the Square for Grillin' & Chillin' First Friday on June 2nd. The evening kicks off in LTown Alley with live music provided by Bethany Yeh, FREE art activities including a Make & Take project from Tape a Friend, Make a Friend, the premiere of the Mad Splatter Shack, an immersive splatter paint activity with Cam Donahue, and an antique and classic car display courtesy of the Leonardtown Arts & Entertainment District and St. Mary's Rod & Classic. Then, enjoy live music from Joseph Norris and tasty eats at Ye Olde Towne Cafe (featuring Jerk Chicken from Jeanine's Chicken) in Leonardtown Square hosted by the Leonardtown Business Association.

View & Download the First Friday Itinerary 

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OctoberFest First Friday
October 6 - 8, 2023

Vote for your favorite Scarecrow decorated by our Leonardtown businesses in the 5th Annual Scarecrow Decorating Contest, don your Lederhosen and join us in the Square for the Bruderfest Parade, visit area businesses for October Fest events and activities including the Bruderfest Celebration at the Brudergarten featuring Weiner Dog and Weiner Dog Wannabe races, Stein Lifting and Barrel Rolling Contests, live music and much more!

Band Performing


Jazzy First Friday
July 7 - 9, 2023

Join us as Leonardtown celebrates all things Jazz during the Potomac Jazz & Seafood Festival Weekend Celebration on Friday, July 7th and Sunday, July 9th. Enjoy live jazz music, brunches, cruises and much more throughout Town (Note: the main event takes place on Saturday, July 8th at the St. Clements Museum in Colton's Point, MD)! 

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Theme TBA



Summer Sizzlin'
First Friday
August 4 - 6, 2023

Enjoy refreshing treats, live music, outdoor movies, and sizzlin' sales all around Town during August's Summer Sizzlin' First Friday on Friday, August 4th - Sunday, August 6th.

Christmas Market


Light Up Leonardtown
First Friday
December 1 - 3, 2023

Take free trolley rides through Town to view Leonardtown done up in its holiday best, vote for your favorite decorated businesses and residences (the winners will receive grand prizes and will be all aglow with the holiday spirit), browse and shop our specialty shops and galleries for one-of-a-kind gifts for everyone on your list, enjoy live music, sweet treats, holiday eats
and more!

First Friday is a year-round event is sponsored by the
Leonardtown Business Association in partnership with the  Town of leonardtown.
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