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Events and Things to do in Windsor, VA this weekend

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

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Things to do around Windsor

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Frequently asked questions about Windsor

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

The best events to attend this weekend in 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:
  • Redd's Oyster Fest
  • The Split Decision Comedy Experience starring Alton Walker | 40th Birthday
  • Love Songs on Sunday's Fall Wellness Festival
  • Ceramic Christmas Tree Painting Class

    • Which events are currently trending in Windsor?

    Trending weekend events in Windsor often reflect seasonal moments, nightlife demand, and popular neighbourhoods, including concerts, parties, and special themed events. The trending searches this month in Windsor are:
  • lounge
  • jazz
  • entertainment
  • celebration

    • Which events are coming up in Windsor this weekend?

    In addition to what's happening right now, there are many upcoming weekend events in Windsor, including live shows, parties, food experiences, and limited-time events. Discover upcoming weekend events you won't want to miss:
  • Bodacious Bazaar Fall 2026
  • Jazz Legacy Gala 2026: Festival Friday
  • Gentle Awakenings Yoga at The Pinner House
  • Sweat & Sip

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

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