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Events and Things to do in Cheltenham, MD this weekend

Looking for things to do in Cheltenham 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 Cheltenham's most popular events.

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Things to do around Cheltenham

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Frequently asked questions about Cheltenham

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

The best events to attend this weekend in Cheltenham 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:
  • Jazz In The Heights 2026
  • THE BOUNCE BACK PICNIC
  • CC Productions Presents: Santana Sunday (Gemini Birthday Celebration)
  • Annual Awards Program

    • Which events are currently trending in Cheltenham?

    Trending weekend events in Cheltenham often reflect seasonal moments, nightlife demand, and popular neighborhoods, including concerts, parties, and special themed events. The trending searches this month in Cheltenham are:
  • kids camp 20623

    • Which events are coming up in Cheltenham this weekend?

    In addition to what's happening right now, there are many upcoming weekend events in Cheltenham, including live shows, parties, food experiences, and limited-time events. Discover upcoming weekend events you won't want to miss:
  • Horsemanship Badge Day | May
  • Crafted Talesâ„¢ Series
  • Why Aren’t You Smiling?: A Meditative Sound Experience
  • The Basement R&B Party | DC

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

    Yes — there are often free things to do in Cheltenham 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 Cheltenham this weekend:
  • Free Events this weekend