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Events and Things to do in Upperville, VA this weekend

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

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Things to do around Upperville

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Frequently asked questions about Upperville

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

The best events to attend this weekend in Upperville 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:
  • Safe At Home 2026: Community Softball Day (Under The Lights)
  • Experience fusion KARAOKE
  • Make Pasta With Mom!
  • 2026 Garden Fair at Blandy Experimental Farm

    • Which events are currently trending in Upperville?

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

    • Which events are coming up in Upperville this weekend?

    In addition to what's happening right now, there are many upcoming weekend events in Upperville, including live shows, parties, food experiences, and limited-time events. Discover upcoming weekend events you won't want to miss:
  • Haymarket Scavenger Hunt For Couples - SHOW LOVE (Date Night!!)
  • 4th Annual Talk Derby to Me Pub Crawl: A Race to Give Back
  • Yoga at the Overlook
  • Holistic Healing Workshop Series Winchester, VA

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

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