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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 Themes

  • January 2, 2026 - A New Year A New You

  • February 6, 2026 - Love In Leonardtown

  • March 6, 2026 - March Madness

  • April 3, 2026 - Sip, Shop & Hop

  • May 1 - May 3, 2026 - Vintage Vibes 

  • June 5 - June 7, 2026 - First Responder

  • July 3 - July 5, 2026 - Red, White & Blues

  • August 7 - August 9, 2026 - Sizzling Sumer

  • September 4 - September 6, 2026 - ArtWalk

  • October 2 - October 4, 2026 - Octoberfest

  • November 6, 2026 - Passport to the Holidays

  • December 4, 2026 - Gingerbread Lane


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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