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Events and Things to do in Rupert, VT this weekend

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

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Things to do around Rupert

Frequently asked questions about Rupert

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

The best events to attend this weekend in Rupert 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:
  • Fit Fest 2026 | Vendor Registration & Sponsorships
  • SYP Summer Soirée – Presented by The Bank of Bennington
  • PMP Training Course | 4-Day PMP Certification Bootcamp in Rutland, VT
  • PMP Exam Prep Bootcamp in Rutland, VT | 35 Contact Hours PMP Training

    • Which events are coming up in Rupert this weekend?

    In addition to what's happening right now, there are many upcoming weekend events in Rupert, including live shows, parties, food experiences, and limited-time events. Discover upcoming weekend events you won't want to miss:
  • Bennington Bash Scavenger Hunt
  • Lively Lake George Scavenger Hunt
  • Charcuterie Board Workshop at Ledge Rock Hill Winery | Wine & Charcuterie
  • Pints and Punchlines at The Parting Glass with headliner Dan Geurin

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

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