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].
## Entertainment Events in Chestertown - **Event Name**: Saturday in the Park! - **Description**: FREE COMMUNITY EVENT LIVE MUSIC 🎶, FOOD, GAMES, and MORE!!! Activities for kids & adults!! - **Interested Audience**: - Count: 152 - **Date**: Sat May 30 2026 at 12:00 pm – Sat May 30 2026 at 04:00 pm (-04:00) - **Event URL**: https://allevents.in/chestertown/saturday-in-the-park/200029809702031 - **Venue**: Wilmer Park - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy84MjRkZjFiODM2NGVmYjNiMzZlODRhMWJkMTFkZWI5MDEyMGJmYmY1NDI5NGM0YWRkYTBjNTdmMWI2YTcxY2IwLXJpbWctdzEyMDAtaDEyMDAtZGNmZmZmZmYtZ21pcj92PTE3NzcwOTA3NDU.avif - **Categories**: kids, music, live-music, entertainment - **Event Name**: LHM debuts @ The Shanty Beach Bar at Tolchester Marina! (Chestertown, MD) - **Description**: Band at 7pm www.lhmband.com https://tolchestermarina.com/t-entertainment-schedule.aspx The Love Hate Mixtape Band offers the ultimate "Live Mixtape" experience. Covering anthems from the 90's Grunge and Alternative Rock Era, to Pop-Punk bangers, radio ro - **Interested Audience**: - Count: 7 - **Date**: Sat May 30 2026 at 07:00 pm (-04:00) - **Event URL**: https://allevents.in/chestertown/lhm-debuts-the-shanty-beach-bar-at-tolchester-marina-chestertown-md/200029979762349 - **Venue**: The Shanty Beach Bar at Tolchester Marina - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy84YjhlYjRkZjgwM2Q5YzBlM2UwZWU3ZjUwNzJkMzU1N2MwODllZWNkMjk4Nzg5NjJhOThkOWY1M2M4MWE5NDMxLXJpbWctdzEyMDAtaDYzNC1kY2VlZGRiZi1nbWlyP3Y9MTc3NjkzODc1MQ.avif - **Categories**: entertainment, music, art, pop, parties - **Event Name**: JJBB at the Shanty Beach Bar at Tolchester Marina - **Description**: We can’t wait to return to the majestic Shanty Beach Bar at Tolchester Marina and deliver our best party rock from the 90’s and 2000’s! - **Interested Audience**: - Count: 9 - **Date**: Fri May 15 2026 at 07:00 pm – Fri May 15 2026 at 11:00 pm (-04:00) - **Event URL**: https://allevents.in/chestertown/jjbb-at-the-shanty-beach-bar-at-tolchester-marina/200029872198319 - **Venue**: The Shanty Beach Bar at Tolchester Marina - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy9kYTRiNWRjYjJlMDQyNDgxNDY1MjczNDJkYzc5NmMxMWZmNzlmOTk3ZWYwYjRkZWMyOGVmNWU5NTdiYzUwYTc1LXJpbWctdzEyMDAtaDEyMDAtZGMzMjQ3NWMtZ21pcj92PTE3NzYyMTcwNTI.avif - **Categories**: parties, entertainment - **Event Name**: 2026 Chestertown Pride Festival - All Ages Dance Party! - **Description**: Join us Friday night in Wilmer Park for an all ages dance party! - **Interested Audience**: - Count: 72 - **Date**: Fri May 01 2026 at 05:00 pm – Fri May 01 2026 at 08:00 pm (-04:00) - **Event URL**: https://allevents.in/chestertown/2026-chestertown-pride-festival-all-ages-dance-party/200029935798637 - **Venue**: 413 S Cross Street, 21620 - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy82ZWM5NjZiNDlhMTQ1NjYzMjE4NzhiYzg1N2I2ODI5NDkyZjg1MDQ5YjFjMTUyOTc4MWRmNWFmZWZlODMzODA3LXJpbWctdzEyMDAtaDc3Mi1kYzdjMTYxNy1nbWlyP3Y9MTc3NzM3ODA3OA.avif - **Categories**: parties, festivals, entertainment, lgbt-pride - **Event Name**: Spongebob Squarepants the Musical - Chestertown - **Description**: 📍 Venue: Garfield Center for the Arts at the Prince Theatre 🏠 Address: 210 High Street, Chestertown, MD 21620 🌆 City: Chestertown 📍 Location: 39.2084, -76.0651✨ Enter a world of endless possibilities at Spongebob Squarepants the Musical - Chester - **Date**: Sat May 02 2026 at 11:00 pm (-05:00) - **Event URL**: https://allevents.in/chestertown/spongebob-squarepants-the-musical-chestertown/3200029950532427 - **Venue**: Garfield Center for the Arts at the Prince Theatre - **Banner**: https://dyn-image.allevents.in/generate-image?v=4&title=Spongebob+Squarepants+the+Musical+-+Chestertown&date=Sat+May+02+2026+at+11%3A00+pm&bg=3 - **Categories**: live-music, art, theatre, trips-adventures - **Event Name**: Summer Launch Party - **Description**: Join MDWA for our Summer Launch Party as we celebrate our newly refreshed space in Chestertown! ☀️ Enjoy light bites, refreshing sips, exciting giveaways, music & permanent jewelry while you explore our new and improved space. All clients, friends, - **Interested Audience**: - Count: 22 - **Date**: Sat May 30 2026 at 12:00 pm – Sat May 30 2026 at 03:00 pm (-04:00) - **Event URL**: https://allevents.in/chestertown/summer-launch-party/200029928017738 - **Venue**: 302 Park Row, Chestertown, MD 21620-1544, United States - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy9kMWJiOTA5YTkzZTcyOWQyZDYyNmY2YWI3YTY2ZDI0MTgxZmM5NDgzZjlmNDZkOTY5MGJkZGZjNzM2ZTM4NGFmLXJpbWctdzEyMDAtaDY3NS1kY2ZmZmRmNS1nbWlyP3Y9MTc3NzEzMTEzMw.avif - **Categories**: parties, entertainment ## Trending Events in Chestertown - **Event Name**: Boyle Sports World Grand Prix Darts - **Description**: The BoyleSports World Grand Prix Darts returns in 2026, bringing world-class darts back to the Mattioli Arena, Leicester. One of the most unique and intense tournaments on the darts calendar, the World Grand Prix features the famous double-start format a - **Venue**: 12 Memory Lane, Leicester - **Banner**: https://cdn-az.allevents.in/events8/banners/78d3207f3285e8184c3b9982429f68ecccb5a1039754f5e732615d345ab8ec1c-rimg-w1080-h1080-dc023d96-gmir?v=1777218634 - **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=1777177487 - **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-dc8bc926-gmir?v=1777389065 - **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**: 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=1777090745 - **Event Name**: LHM debuts @ The Shanty Beach Bar at Tolchester Marina! (Chestertown, MD) - **Description**: Band at 7pm www.lhmband.com https://tolchestermarina.com/t-entertainment-schedule.aspx The Love Hate Mixtape Band offers the ultimate "Live Mixtape" experience. Covering anthems from the 90's Grunge and Alternative Rock Era, to Pop-Punk bangers, radio ro - **Venue**: The Shanty Beach Bar at Tolchester Marina - **Banner**: https://cdn-az.allevents.in/events8/banners/8b8eb4df803d9c0e3e0ee7f5072d3557c089eecd29878962a98d9f53c81a9431-rimg-w1200-h634-dceeddbf-gmir?v=1776938751 - **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 ## 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**: What are the top Entertainment events in Chestertown? - **A:** Saturday in the Park! (Sat May 30 2026 at 12:00 pm at Wilmer Park), LHM debuts @ The Shanty Beach Bar at Tolchester Marina! (Chestertown, MD) (Sat May 30 2026 at 07:00 pm at The Shanty Beach Bar at Tolchester Marina), JJBB at the Shanty Beach Bar at Tolchester Marina (Fri May 15 2026 at 07:00 pm at The Shanty Beach Bar at Tolchester Marina), 2026 Chestertown Pride Festival - All Ages Dance Party! (Fri May 01 2026 at 05:00 pm at 413 S Cross Street, 21620), Spongebob Squarepants the Musical - Chestertown (Sat May 02 2026 at 11:00 pm at Garfield Center for the Arts at the Prince Theatre). - **Q**: What Entertainment events are happening in Chestertown this weekend May 1–3, 2026? - **A:** 2026 Chestertown Pride Festival - All Ages Dance Party! (Fri May 01 2026 at 05:00 pm at 413 S Cross Street, 21620), Spongebob Squarepants the Musical - Chestertown (Sat May 02 2026 at 11:00 pm at Garfield Center for the Arts at the Prince Theatre). - **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**: What are the popular venues for Entertainment events in Chestertown? - **A:** Some popular venues hosting Entertainment events in Chestertown include Wilmer Park, The Shanty Beach Bar at Tolchester Marina, 413 S Cross Street, 21620. - **Q**: What is the price range for Entertainment events in Chestertown? - **A:** Prices for Entertainment events in Chestertown range from USD 34 to USD 215. Many events also offer free entry. - **Q**: Who are the top organizers for Entertainment events in Chestertown? - **A:** Popular organizers hosting Entertainment events in Chestertown include Chestertown Recreation, Love Hate Mixtape, JJ Billings Band. - **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 Worton](https://allevents.in/worton/entertainment) - [Entertainment events in Kennedyville](https://allevents.in/kennedyville/entertainment) - [Entertainment events in Rock Hall](https://allevents.in/rock-hall/entertainment) - [Entertainment events in Sudlersville](https://allevents.in/sudlersville/entertainment) - [Entertainment events in Massey](https://allevents.in/massey/entertainment) - [Entertainment events in Cecilton](https://allevents.in/cecilton/entertainment)