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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:
  • Sunday Showcase: May Edition
  • VIP President's Tour 2026, 10am - 12:15pm
  • Oppression, Dehumanization, and the Work of Humanization
  • Island Feva Memorial Day Weekend Bash

    • Which events are currently trending in Ossining?

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

    • 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:
  • The Stories We Share: New Castle Historical Society's Jubilee Exhibition
  • Stamford Showdown Scavenger Hunt
  • Museum Admission
  • 90-min. Guided House Tour: 12 – 1:30pm (Now – June 10, 2026)

    • 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