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Events and Things to do in Chestertown, MD this weekend

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

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Things to do around Chestertown

Trends in Chestertown

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Frequently asked questions about Chestertown

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

The best events to attend this weekend in Chestertown 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:
  • Schooner SULTANA Public Sails 2026-May
  • Qigong Class
  • Bohemia Manor Winery: Tour and Taste
  • Drag Bingo - Perry Hall, MD - May 2

    • Which events are currently trending in Chestertown?

    Trending weekend events in Chestertown often reflect seasonal moments, nightlife demand, and popular neighbourhoods, including concerts, parties, and special themed events. The trending searches this month in Chestertown are:
  • washington college concert
  • kent county
  • chestertown car show
  • events happening today near me

    • Which events are coming up in Chestertown this weekend?

    In addition to what's happening right now, there are heaps of upcoming weekend events in Chestertown, including live shows, parties, food experiences, and limited-time events. Discover upcoming weekend events you won't want to miss:
  • 90's R&B: Sip and Paint Vibes – A Night of Art, Wine & Nostalgia!
  • GCA Presents "The Spongebob Musical" NEW DATES
  • Head of The Chester Public Paddle- 2026- Sultana Education Foundation
  • Holding Change Workshop Series~ Caregiving, Grief & Loss, & Life Transition

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

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