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Events and Things to do in Annapolis, MD this weekend

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

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Things to do around Annapolis

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Frequently asked questions about Annapolis

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

The best events to attend this weekend in Annapolis 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:
  • The Masquerade Affair Presented by DJ Prez & DJ Kelly Kellz
  • Prezzy's Annual All Black Everything 2026
  • GVO SOUND PRESENTS: Trick or Freak! Halloween Costume Party!!
  • Halloween Masquerade Ball

    • Which events are currently trending in Annapolis?

    Trending weekend events in Annapolis often reflect seasonal moments, nightlife demand, and popular neighbourhoods, including concerts, parties, and special themed events. The trending searches this month in Annapolis are:
  • halloween party
  • halloween festival
  • trunk or treat
  • fall

    • Which events are coming up in Annapolis this weekend?

    In addition to what's happening right now, there are heaps of upcoming weekend events in Annapolis, including live shows, parties, food experiences, and limited-time events. Discover upcoming weekend events you won't want to miss:
  • ⁠Mindful Wellness Walk in Annapolis
  • Amazing Annapolis Scavenger Hunt
  • Mini Birth Class
  • Wild & Rooted

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

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