Your version of Internet Explorer is not longer supported. Please upgrade your browser.

Events and Things to do in Chester, MD this weekend

Looking for things to do in Chester 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 Chester'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 136

Things to do around Chester

Trends in Chester

Explore more trends
Explore more trends

Frequently asked questions about Chester

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

The best events to attend this weekend in Chester 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
  • Laughs in the Lounge
  • Come Out and Play in DMV/Annapolis 2026
  • Rodgers & Hammerstein's Oklahoma!

    • Which events are currently trending in Chester?

    Trending weekend events in Chester often reflect seasonal moments, nightlife demand, and popular neighbourhoods, including concerts, parties, and special themed events. The trending searches this month in Chester are:
  • pubcrawl
  • crawl
  • comedy
  • speeddating

    • Which events are coming up in Chester this weekend?

    In addition to what's happening right now, there are many upcoming weekend events in Chester, 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
  • St. Michaels, Maryland Scavenger Hunt
  • Amazing Annapolis Scavenger Hunt
  • Waterman's Crab House 80's Murder Mystery Dinner & Show

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

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