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Community Events and Things to do in New Windsor, NY this weekend

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

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Things to do around New Windsor

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Frequently asked questions about New Windsor

What are the best events to attend this weekend in New Windsor?

The best events to attend this weekend in New Windsor 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:
  • Farm Day (Volunteer Work Days)
  • The Road to Queendom Presents: Paint & Affirm (Mother’s Day Experience)
  • RevWar250 : The Spy and the Traitor: The André-Arnold Affair Bus Daytrips
  • Bloom & Bond Plant Bingo

    • Which events are currently trending in New Windsor?

    Trending weekend events in New Windsor often reflect seasonal moments, nightlife demand, and popular neighbourhoods, including concerts, parties, and special themed events. The trending searches this month in New Windsor are:
  • orange county
  • christian concerts
  • speed dating over 50
  • hudson valley wine

    • Which events are coming up in New Windsor this weekend?

    In addition to what's happening right now, there are many upcoming weekend events in New Windsor, 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
  • Wonderful Woodstock Scavenger Hunt
  • 90-min. Guided House Tour: 12 – 1:30pm (Now – June 10, 2026)

    • Are there free things to do in New Windsor this weekend?

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