Make your life happening by enrolling to entertainment events in [CITY]. Find a partner through a salsa night or take your partner to live in concerts by upcoming bands in your town. Get high while playing Beer Pong in a pub crawl or attending stand-up comedy events in [CITY]. Shake your legs in the happy streets, zumba or dance workshops or go for a film screening in the nearby cafes or theaters.
Explore Entertainment Events in [CITY].
## Trending Events in Chestertown - **Event Name**: The 30th Annual Chestertown Tea Party Distance Classic Race and Run for Radcliffe (5K & 10-Mile Run) - **Description**: Radcliffe Creek School is excited to host the 30th Annual Chestertown Tea Party Distance Classic Race and Run for Radcliffe. As is tradition, the run will help kick off Chestertown's Annual Tea Party Festival on Saturday, May 23, 2026! Hundreds of runner - **Venue**: Wilmer Park - **Event Name**: Armageddon XL - **Description**: ARMAGEDDON 2026 MDA Events and MODUS Sports are proud to announce the return of one of the biggest darts events of the year, Armageddon 2026. Following the overwhelming success of Armageddon 2025 – Rivalries Renewed, we are going even bigger for 2026. T - **Venue**: 12 Memory Lane, Leicester - **Banner**: https://cdn-az.allevents.in/events3/banners/2705356057b84ab53fa30178c8b1f2d50b9ba19410226ea4b3153654deb6c552-rimg-w1080-h1080-dca39592-gmir?v=1776281296 - **Event Name**: 2026 Chestertown Pride Festival! - **Description**: Join us Saturday in Wilmer Park for Live Music, Food, Drag Performers, Vendors, Family Fun, Community resources & More! For more info visit chestertownpride.com - **Venue**: 413 S Cross Street, 21620 - **Banner**: https://cdn-az.allevents.in/events10/banners/b780e734c9429b52a31985335d91c5a2ad4a207e84b77ba1f099ffe1fcab6bc0-rimg-w1200-h1552-dcfffffe-gmir?v=1776063396 - **Event Name**: Saturday in the Park! - **Description**: FREE COMMUNITY EVENT LIVE MUSIC 🎶, FOOD, GAMES, and MORE!!! Activities for kids & adults!! - **Venue**: Wilmer Park - **Banner**: https://cdn-az.allevents.in/events8/banners/824df1b8364efb3b36e84a1bd11deb90120bfbf54294c4adda0c57f1b6a71cb0-rimg-w1200-h1200-dcffffff-gmir?v=1776282052 - **Event Name**: GCA Presents "The Spongebob Musical" NEW DATES - **Description**: Who lives in a pineapple under the sea and became the hottest star on Broadway? Why, it's SpongeBob SquarePants! Live on stage!About this EventPlunge into this stunning all-singing, all-dancing, dynamic stage show! When t - **Venue**: Garfield Center for the Arts at the Prince Theatre - **Banner**: https://cdn-az.allevents.in/events7/banners/f316877c2a59afb432fad9a7c13b0644f73569fd027ef7f108ba7a3703fae74b-rimg-w1200-h648-dc03182e-gmir.jpg?v=1774381961 - **Event Name**: Sultana's Annual Gala, May 9, 2026 - **Description**: It's Sultana's 28th party with a cause!...Join us on May 9, 2026,  for Sultana Education Foundation's Annual Gala.About this EventIt's time to celebrate again!...Join us on May 9, 2026, for Sultana Education Foundation's - **Venue**: Clovelly Farm - **Banner**: https://cdn-az.allevents.in/events6/banners/e8cab76be10868b6c8b7141714a8989f82c8696851ec87c29f942d5b64be2b1c-rimg-w1200-h825-dc191817-gmir.jpg?v=1769346817 - **Event Name**: Schooner SULTANA Public Sails 2026-May - **Description**: Departing and returning from SULTANA’s port of historic Chestertown, SULTANA’s two-hour public sails are a great way to sail the ChesterAbout this EventDeparting and returning from SULTANA’s home port of historic Chester - **Venue**: Chestertown Marina - **Banner**: https://cdn-az.allevents.in/events8/banners/efc2cf85253fbb9d95a677ac64fb33cc2acdcbbaa93f110c69ad94bcb6f070b4-rimg-w1000-h801-dcd3d8d6-gmir.jpg?v=1769346989 - **Event Name**: Rt 50 live at Rolph’s Wharf Sandbar! - **Description**: We are very excited to be back at Rolph’s Wharf! Such a great spot! Come by car, come by boat, come by seaplane! Bring your friends, bring your family, bring your dog! The next day is a holiday (Memorial day) so there’s no excuse not to come! - **Venue**: Rolph's Wharf Sandbar - **Banner**: https://cdn-az.allevents.in/events1/banners/4c00145c180c5d2223f4446c110ec47fd2ed16fca7e2bb9f6b70b86b3cb52824-rimg-w1170-h650-dcababa7-gmir?v=1776331803 - **Event Name**: Schooner SULTANA Public Sails 2026-June - **Description**: Departing and returning from SULTANA’s port of historic Chestertown, SULTANA’s two-hour public sails are a great way to sail the ChesterAbout this EventDeparting and returning from SULTANA’s home port of historic Chester - **Venue**: Chestertown Marina - **Banner**: https://cdn-az.allevents.in/events8/banners/77c1884eff212e997bfea5e50ddf4767778a36727184a3c8081cfc4d4b36a362-rimg-w1000-h801-dcd3d8d6-gmir.jpg?v=1769346987 ## Browse Entertainment Events by Date - [Entertainment Events Today in Chestertown](https://allevents.in/chestertown/entertainment--today) - [Entertainment Events This Weekend in Chestertown](https://allevents.in/chestertown/entertainment--this-weekend) - [Entertainment Events in April in Chestertown](https://allevents.in/chestertown/entertainment--april) - [Entertainment Events in May in Chestertown](https://allevents.in/chestertown/entertainment--may) ## FAQs - **Q**: How can I find Entertainment events in Chestertown? - **A:** You can discover upcoming Entertainment events in Chestertown on AllEvents.in. Browse by date, venue, or price to find events that match your interests. - **Q**: How do I buy tickets for Entertainment events in Chestertown? - **A:** You can buy tickets directly through AllEvents.in. Many events offer online booking with options for free, paid, and early-bird tickets. - **Q**: Are there any online Entertainment events available? - **A:** Yes, many Entertainment events are available online. You can filter for virtual events on AllEvents.in to attend from anywhere. - **Q**: How can I get notified about new Entertainment events in Chestertown? - **A:** Follow the Entertainment category on AllEvents.in to get notified when new Entertainment events are listed in Chestertown. ## Category Banner - **Banner Image**: https://cdn2.allevents.in/transup/58/5efbefdb8e438db5c829e697673309/Maskgroup-3-.webp ## Entertainment events from nearby cities - [Entertainment events in North Creek](https://allevents.in/north-creek/entertainment) - [Entertainment events in Schroon Lake](https://allevents.in/schroon-lake/entertainment)