Your version of Internet Explorer is no longer supported. Please upgrade your browser.

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.

1 filter applied
Filters (1)
This weekend
Category
Format
Price
Language
Currency
1 filter applied
Filters (1)
This weekend
  • 1 of 122

Things to do around Annapolis

Trends in Annapolis

Explore more trends
Explore more trends

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:
  • 2026 Fall Craft Fair
  • The Author Space Book & Art Festival
  • Maryland Icon Athletics 4th Annual Purple Premiere 26-27
  • The All Black Affair • Grown Folks Weekend Getaway

    • 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
  • free paper shredding

    • Which events are coming up in Annapolis this weekend?

    In addition to what's happening right now, there are many 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:
  • Come Out and Play in DMV/Annapolis 2026
  • Rodgers & Hammerstein's Oklahoma!
  • Book of Days
  • Bowie State Fall 2026 Induction

    • 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