# Live Music in Chestertown, MD 2026 | Gigs, Bands & Concerts - **Subtitle**: Discover live music in Chestertown, Maryland. Book tickets for gigs, band performances, jazz nights and live concerts happening across the city. Find your next show today. - **Category**: Live Music - **Type**: other ## Audience - **Followers**: 1.1M+ - **Recent Followers**: - **Avatar 1**: https://cdn-az.allevents.in/events1/banners/37479823079c9f83d2914976fdcfcf4967f2016c3711e7a943c35899be94db13-rimg-w200-h200-gmir.jpg?v=1602211399 - **Avatar 2**: https://cdn-az.allevents.in/events5/banners/cfb32890-948d-11f0-bd3d-c172f57c4c49-rimg-w200-h200-dcf5f5f5-gmir - **Avatar 3**: https://cdn-az.allevents.in/events5/banners/5a8c7ca0-a4ce-11f0-9e53-fbf656aababc-rimg-w200-h200-dc7a501f-gmir ## Featured Events - **Event Name**: FEST OF SPRING 2026: Wine, Food & Music Festival - **Description**: Join us for a great time with International Music, Cuisine & more at the Fest of Spring Wine, Food, and Music Festival!Indulge in a variety of International & local cuisine.Savor fine wines from the region, paired perfectly with y - **Date**: Sat, 13 Jun at 01:00 pm – Sat, 13 Jun at 09:00 pm (-04:00) - **Event URL**: https://allevents.in/baltimore/fest-of-spring-2026-wine-food-and-music-festival-tickets/80002698494740 - **Venue**: Carroll Park - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:600:300/g:sm/sh:100/aHR0cHM6Ly9jZG4yLmFsbGV2ZW50cy5pbi90aHVtYnMvdGh1bWI2OWU1YWY2ZDdiNGU5LmpwZw.avif - **Price**: min: 0, max: 99.99, currency: USD - **Categories**: festivals, food-truck-festivals, music-festivals, music, entertainment, wine-tasting, spring-break, food-drinks, nonprofit, kids, reggae ## About For the ones whose heart beats for music, live music events are something that you will absolutely enjoy. Groove on the most upbeat songs and enjoy the best of live music in [CITY]. You will find music of all kinds and genres, discover the ones that fit your interests and enjoy the spellbinding surroundings near you. You will be in a constant dilemma what to choose and what to drop, because there is music beating all around the city. From jazz nights at the jazz clubs to soulful musical events at the best live music venues in [CITY]. Discover all the mesmerizing and all the heavy & loud music events near you. ## Live Music Events in Chestertown - **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 - **Interested Audience**: - Count: 71 - **Date**: Sat May 02 2026 at 01:00 pm – Sat May 02 2026 at 05:00 pm (-04:00) - **Event URL**: https://allevents.in/chestertown/2026-chestertown-pride-festival/200029935798336 - **Venue**: 413 S Cross Street, 21620 - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEwL2Jhbm5lcnMvYjc4MGU3MzRjOTQyOWI1MmEzMTk4NTMzNWQ5MWM1YTJhZDRhMjA3ZTg0Yjc3YmExZjA5OWZmZTFmY2FiNmJjMC1yaW1nLXcxMjAwLWgxNTUyLWRjZmZmZmZlLWdtaXI_dj0xNzc2Njg4Mzkx.avif - **Categories**: festivals, music, entertainment, lgbt-pride, performances, live-music, music-festivals - **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**: Loveboat Yacht Rock at the Shanty Bar at Tolchester Marina - **Description**: Loveboat is a Baltimore/Washington area based band of talented and tenured musicians with a common set of goals: to entertain music lovers with some of the greatest songs ever written back in the late 70's and early 80's, and to have as much fun as possib - **Interested Audience**: - Count: 16 - **Date**: Fri Sep 04 2026 at 01:00 pm (-04:00) - **Event URL**: https://allevents.in/chestertown/loveboat-yacht-rock-at-the-shanty-bar-at-tolchester-marina/200029868967358 - **Venue**: The Shanty Beach Bar at Tolchester Marina - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy80ZGUyNGMyZWZiMTY4ZjMxMDkxOTJhYWI2Y2Q2OWU2NzBmMGE1NzdkNTgxMTBhZDZkYTRjMWUwMjFjZGJlZWU2LXJpbWctdzEyMDAtaDU2Ny1kYzAxMDFiYS1nbWlyP3Y9MTc3NzEyNDAxNg.avif - **Categories**: entertainment, music, performances, workshops, boat-parties, parties - **Event Name**: The High and Wides with Caleb Stine - **Description**: The High and Wide's return to the Garfield Stage, joining them will be singer/songwriter Caleb Stine - **Date**: Fri May 08 2026 at 08:00 pm – Fri May 08 2026 at 10:00 pm (-04:00) - **Event URL**: https://allevents.in/chestertown/the-high-and-wides-with-caleb-stine/100001986330493978 - **Venue**: Garfield Center for the Arts at the Prince Theatre - **Banner**: https://dyn-image.allevents.in/generate-image?v=4&title=The+High+and+Wides+with+Caleb+Stine&date=Fri+May+08+2026+at+08%3A00+pm&bg=4 - **Price**: USD 29 - **Categories**: music ## 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-dcfffffe-gmir?v=1776688391 - **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 Live Music Events by Date - [Live Music Events Today in Chestertown](https://allevents.in/chestertown/live-music--today) - [Live Music Events This Weekend in Chestertown](https://allevents.in/chestertown/live-music--this-weekend) - [Live Music Events in April in Chestertown](https://allevents.in/chestertown/live-music--april) - [Live Music Events in May in Chestertown](https://allevents.in/chestertown/live-music--may) ## FAQs - **Q**: What are the top Live Music events in Chestertown? - **A:** 2026 Chestertown Pride Festival! (Sat May 02 2026 at 01:00 pm at 413 S Cross Street, 21620), 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), Loveboat Yacht Rock at the Shanty Bar at Tolchester Marina (Fri Sep 04 2026 at 01:00 pm at The Shanty Beach Bar at Tolchester Marina), The High and Wides with Caleb Stine (Fri May 08 2026 at 08:00 pm at Garfield Center for the Arts at the Prince Theatre). - **Q**: What Live Music events are happening in Chestertown this weekend May 1–3, 2026? - **A:** 2026 Chestertown Pride Festival! (Sat May 02 2026 at 01:00 pm at 413 S Cross Street, 21620). - **Q**: How can I find Live Music events in Chestertown? - **A:** You can discover upcoming Live Music 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 Live Music 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 Live Music events in Chestertown? - **A:** Some popular venues hosting Live Music events in Chestertown include 413 S Cross Street, 21620, Wilmer Park, The Shanty Beach Bar at Tolchester Marina. - **Q**: What is the price range for Live Music events in Chestertown? - **A:** Prices for Live Music events in Chestertown range from USD 29 to USD 100. Many events also offer free entry. - **Q**: Who are the top organizers for Live Music events in Chestertown? - **A:** Popular organizers hosting Live Music events in Chestertown include Chestertown Pride Festival, Chestertown Recreation, Love Hate Mixtape. - **Q**: What types of Live Music events can I find in Chestertown? - **A:** You can explore a variety of live music sub-genres and styles including Hip Hop Music, House Music, Classical Music, Afrobeats, Bachata and more. - **Q**: Are there any online Live Music events available? - **A:** Yes, many Live Music 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 Live Music events in Chestertown? - **A:** Follow the Live Music category on AllEvents.in to get notified when new Live Music events are listed in Chestertown. ## Live Music from nearby cities - [Live Music in Worton](https://allevents.in/worton/live-music) - [Live Music in Rock Hall](https://allevents.in/rock-hall/live-music) - [Live Music in Sudlersville](https://allevents.in/sudlersville/live-music) - [Live Music in Centreville](https://allevents.in/centreville-md/live-music) - [Live Music in Galena](https://allevents.in/galena-md/live-music) - [Live Music in Massey](https://allevents.in/massey/live-music) - [Live Music in Queenstown](https://allevents.in/queenstown-md/live-music) - [Live Music in Cecilton](https://allevents.in/cecilton/live-music)