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  • May
  • W21
    • Chopticon Spring Band Banquet
    • Spirit Night at Social
  • T22
    • Leprechaun Lilly's Consignment Sale - Spring/Summer 2025
    • Reviving Small Towns: Building Resilient Communities for the Future
  • F23
    • JUMP: AMERICAS VAN HALEN EXPERIENCE | Leonardtown, MD
    • Summer Splash ~ Silent Disco
    • Crafting Cohort: RenFest SoMD
    • Mommy + Me Workout Class
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  • S24
    • RenFest Southern Maryland
    • Spin It Again at Renfest So MD
    • Mandala Coaster Coloring at SMC Arts Council
    • Public Domain: Restoration Dance Party
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  • S25
    • DIY Porch Makeover Workshop - Make a Doormat & Porch Sign!
    • ALL-YOU-CAN-EAT SPAGHETTI SUNDAYS AT LEDO PIZZA!
    • Spin It Again at RenFest So MD
  • M26
  • T27
    • Flower Pot Painting
    • Neighborhood Nail Trim Day- Clark’s Rest and Leonard’s Grant
    • Imaginarium Play Group with SMCHD
  • W28
  • T29
  • F30
    • Mommy + Me Workout Class
    • (Friday event} Salsa On The Vine at The Port of Leonardtown Winery.
    • Pax Jam
    • Sunset Cruise @ Leonardtown Wharf
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  • S31
  • Jun
  • S1
    • Cars & Coffee Car Show
  • M2
  • T3
    • Tractor Maintenance for Farmers: Keep Your Tractor Running Smoothly
  • W4
    • Flower Cookie Decorating with Selina's Sweets
    • Launch & Learn
    • Coffee Time with Dee
  • T5
    • Uncorked & Unveiled - a fundraiser for St. Mary's County Arts Council!
  • F6
    • Create a Collage of Your Favorite Sweet- FREE Activity
    • First Friday Meet & Greet - Annise Jefferson (SoMD Sugar Show)
    • SOLD OUT-Glass Blowing w/McFadden Glass-Port of Leonardtown Winery
    • The Old Jail Museum Open for Leonardtown First Fridays (Extended Hours)
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  • S7
    • Robbie Boothe Band - Leonardtown Square! ONE NIGHT ONLY!
    • Wines of the World Tasting
    • HydraFX Concert
    • St. Mary’s County Juneteenth
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  • S8
  • M9
    • SMAWL Vaccination Clinic
  • T10
    • Launch & Learn
  • W11
  • T12
  • F13
    • The Fenwick Inn Art Exhibit and Sale
    • 2025 Second Friday Socials at SMC Arts Council
  • S14
    • St Mary's Crab Festival
    • Flag Day Celebration
    • The Fabulous Hubcaps at The St Mary's County Crab Festival
    • Thunderball at The St Mary's County Crab Festival
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  • S15
    • Cars & Coffee Car Show
    • Bootleggers at POL Winery
    • Free Admission for Dads on Father's Day at the St. Mary's County Museums
  • M16
  • T17
  • W18
    • Booze & Tattoos
    • Charles County Crime Solvers Golf Tournament ⛳
  • T19
  • F20
    • SOLD OUT-June 20th Glass Blowing @Port of Leonardtown Winery
  • S21
    • Storytime in the Park (Port of Leonardtown Park)

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