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Community Events and Things to do in Ossining, NY this weekend

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

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Things to do around Ossining

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Frequently asked questions about Ossining

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

The best events to attend this weekend in Ossining 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:
  • Nocturnal Night Walk
  • Riverside Moguls, Part 3: Five Sleeping Giants
  • Reading and Q&A with Lorraine Ash
  • Sleepy Hollow Strolls: Guided walking tours of Tarrytown and Sleepy Hollow

    • Which events are currently trending in Ossining?

    Trending weekend events in Ossining often reflect seasonal moments, nightlife demand, and popular neighbourhoods, including concerts, parties, and special themed events. The trending searches this month in Ossining are:
  • murder mystery westchester ny
  • street fairs
  • mothers day
  • lesbian

    • Which events are coming up in Ossining this weekend?

    In addition to what's happening right now, there are many upcoming weekend events in Ossining, including live shows, parties, food experiences, and limited-time events. Discover upcoming weekend events you won't want to miss:
  • Stamford Showdown Scavenger Hunt
  • Museum Admission
  • 45-min. Guided House Tour: 1 – 1:45pm (Oct. 7 – Nov. 25, 2026)
  • Guided Tour of Manhattan's Last Farmhouse!

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

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