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Community Events and Things to do in Leonardtown, MD this weekend

Looking for things to do in Leonardtown this weekend? Explore our real-time listings for the best concerts, nightlife, and food and drink experiences. From seasonal festivals and comedy shows to free activities, find your next plan with our constantly updated feed of Leonardtown's most popular events.

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Things to do around Leonardtown

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Frequently asked questions about Leonardtown

What are the best events to attend this weekend in Leonardtown?

The best events to attend this weekend in Leonardtown include concerts, nightlife experiences, seasonal events, food and drink tastings, and live entertainment happening across the city. According to Eventbrite, some of the best events this weekend include:
  • The Obsession Homecoming
  • LaCasa's 4th Annual Kentucky Derby Experience 2026
  • Pop-Up & Grow Weekend Market
  • Social Sundays with Push Play featuring D. Floyd

    • Which events are currently trending in Leonardtown?

    Trending weekend events in Leonardtown often reflect seasonal moments, nightlife demand, and popular neighborhoods, including concerts, parties, and special themed events. The trending searches this month in Leonardtown are:
  • car shows
  • st marys county maryland
  • free kids events
  • 5k

    • Which events are coming up in Leonardtown this weekend?

    In addition to what's happening right now, there are many upcoming weekend events in Leonardtown, including live shows, parties, food experiences, and limited-time events. Discover upcoming weekend events you won't want to miss:
  • Arlington National Cemetery, CIA Memorial Wall Tour
  • May the 4th (Force) be with you-8th Street SE Unofficial Star Wars Weekend
  • Cliff and Cle First Friday at Diablos Cantina!
  • 3rd Annual National Urban Farm Festival

    • Are there free things to do in Leonardtown this weekend?

    Yes — there are often free things to do in Leonardtown this weekend, including live music, cultural events, seasonal activities, and community gatherings. Many events on Eventbrite are free or offer free entry options. These are some free events happening in Leonardtown this weekend:
  • Free Events this weekend