# Live Music in Chestertown, MD | Gigs, Bands & Nights Out - **Subtitle**: Find live music in Chestertown, Maryland tonight, tomorrow and this weekend. Discover gigs, bands and open-mic nights at bars and venues near you. - **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**: 2026 Sultana Downrigging Festival Music Village Passes - **Description**: In the past two decades, Sultana Downrigging has grown to be one of the largest Tall Ship gatherings in the country.About this EventWhat do you get when you combine the largest annual gathering of Tall Ships in North Amer - **Date**: Fri, 30 Oct at 03:00 pm – Sun, 01 Nov at 04:00 pm (-04:00) - **Event URL**: https://allevents.in/chestertown/2026-sultana-downrigging-festival-music-village-passes/100001990501810498 - **Venue**: Chestertown Marina - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:600:300/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy8zNDdiNzE4ZmRkYmZiNDk4ZDRhNmYwMWIxMTFhYjBjODEyN2MwMTYzYzEzZWMxNTljODhhMWEwZWJlOGNmZTA2LXJpbWctdzEyMDAtaDgwMC1kY2YxZjNmMS1nbWlyLmpwZz92PTE3ODAzNTc1MzA.avif - **Price**: min: 28.1, max: 65.19, currency: USD - **Categories**: fitness, Festivals, Nonprofit ## 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 Chestertown. 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 Chestertown. Discover all the mesmerizing and all the heavy & loud music events near you. ## Live Music Events in Chestertown - **Event Name**: Dan Paisley & The Southern Grass - **Description**: Dan Paisley & The Southern Grass is back for another great night of Bluegrass at the Chestertown Volunteer Fire Company!About this EventTickets will be available for purchase at the door for $30. Food will also be ava - **Date**: Sat Nov 14 2026 at 07:00 pm – Sat Nov 14 2026 at 09:00 pm (-05:00) - **Event URL**: https://allevents.in/chestertown/dan-paisley-and-the-southern-grass/100002003300807643 - **Venue**: Chestertown Volunteer Fire Co - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy8wMGYxYjVjZWQxZDYyY2Q1NDQwNzc1YjM0ZGEwODhlMmJkNDllZTNlYTBiNmI5NjY1MjlhNzgyZjBkNzZhYTVhLXJpbWctdzEwODQtaDE0NTEtZGMwODA4MDgtZ21pci5qcGc_dj0xNzkxOTE5ODYz.avif - **Price**: USD 29 - **Categories**: fitness ## Trending Events in Chestertown - **Event Name**: 2026 Sultana Downrigging Festival Music Village Passes - **Description**: In the past two decades, Sultana Downrigging has grown to be one of the largest Tall Ship gatherings in the country.About this EventWhat do you get when you combine the largest annual gathering of Tall Ships in North Amer - **Venue**: Chestertown Marina - **Banner**: https://cdn-az.allevents.in/events6/banners/347b718fddbfb498d4a6f01b111ab0c8127c0163c13ec159c88a1a0ebe8cfe06-rimg-w1200-h800-dcf1f3f1-gmir.jpg?v=1780357530 - **Event Name**: 2026 Downrigging Tall Ship Sails: SATURDAY OCT 31 (afternoon),2:30pm-5:00pm - **Description**: The Sultana Education Foundation’s Downrigging offers opportunities to sail the Chester River on your choice of 9 historic tall ships.About this EventAbout This EventThe Sultana E - **Venue**: Chestertown Marina - **Banner**: https://cdn-az.allevents.in/events9/banners/4c41740502bb61cfeb4c20f3a2ad065139017cec2a8d489e8fd7c487c0449f04-rimg-w1200-h801-dc6392c2-gmir.jpg?v=1780357520 - **Event Name**: 2026 Downrigging Tall Ship Sails: SUNDAY NOV 1, 1:00pm-3:30pm - **Description**: The Sultana Education Foundation’s Downrigging offers opportunities to sail the Chester River on your choice of 9 historic tall ships.About this EventAbout This EventThe Sultana E - **Venue**: Chestertown Marina - **Banner**: https://cdn-az.allevents.in/events4/banners/66cd62ba701bc4071cd68c87fcded7f6bcbb9bf33cfe8344ac73421c3354c435-rimg-w1200-h801-dc6392c2-gmir.jpg?v=1780357532 - **Event Name**: 2026 Downrigging Tall Ship Sails: FRIDAY OCT 30, 2:30pm-5:00pm - **Description**: The Sultana Education Foundation’s Downrigging offers opportunities to sail the Chester River on your choice of 9 historic tall ships.About this EventAbout This EventThe Sultana E - **Venue**: Chestertown Marina - **Banner**: https://cdn-az.allevents.in/events1/banners/dd3f2be5c77fff64314d0edc93466c2c6c4a65fc2170624c1c4987c88d085a0d-rimg-w1200-h801-dc6392c2-gmir.jpg?v=1780357508 - **Event Name**: Waterfowl and Foliage Public Paddle - 2026- Sultana Education Foundation - **Description**: Come explore the beautiful tidal Morgan Creek, one of the best spots for bird watching and leaf peeping on the Eastern ShoreAbout this EventCome explore the beautiful tidal Morgan Creek, one of the best spots for bird wat - **Venue**: Rileys Mill Landing - **Banner**: https://cdn-az.allevents.in/events7/banners/2b93ff22c5c1a7f0a9522a0b521efabd6447feb519bcaa3631840edf72e5051a-rimg-w1200-h675-dc191a15-gmir.jpg?v=1768052670 - **Event Name**: 2026 Downrigging Tall Ship Sails: SATURDAY OCT 31 (morning), 10:30am-1:00pm - **Description**: The Sultana Education Foundation’s Downrigging offers opportunities to sail the Chester River on your choice of 9 historic tall ships.About this EventAbout This EventThe Sultana E - **Venue**: Chestertown Marina - **Banner**: https://cdn-az.allevents.in/events8/banners/dea2fb9d2943ed97fdeece4417736e414c8c9dae712166e839a799802217cde8-rimg-w1200-h801-dc6392c2-gmir.jpg?v=1780357511 - **Event Name**: Spooky Music Class - Ages 6 months - 3 years - **Description**: A fun, festive parent-n-me focused music class filled with songs, movement and Halloween fun! For ages 6 months - 3 years. $15 per child. Costumes and festive clothing encouraged! - **Venue**: 115 S Lynchburg St, Suite D, Chestertown, MD, United States, Maryland 21620 - **Banner**: https://cdn-az.allevents.in/events7/banners/f821e1f2ddc0f20dcee29b4db1a8390352c69b727b6654344632b832dbde0721-rimg-w1024-h1536-dcf8f8e8-gmir?v=1791051476 - **Event Name**: Historic Chestertown Ghost Walks - **Description**: Step into the shadows of the past on a Historic Chestertown Ghost Walk. Join the fun… if you dare! A costumed guide will light the path with a lantern on a walk through centuries of stories, told against a backdrop of local history. You'll move through - **Venue**: Bordley History Center - **Banner**: https://cdn2.allevents.in/thumbs/thumb6ac53a8bd3a14.jpg - **Event Name**: Intro to Instruments - Ages 4-6 - **Description**: Introducing our Intro to Instruments Class for Ages 4-6 every other Saturday morning! This is perfect for families who can't commit to weekly lessons or classes but still want to introduce their kiddos' to playing instruments and singing! Wanna sign up? C - **Venue**: 115 S Lynchburg St, Suite D, Chestertown, MD, United States, Maryland 21620 - **Banner**: https://cdn-az.allevents.in/events5/banners/73c56ecee1ad11ddf8dcf4a159a69b707b70b2fd54c9e0c4bb46402e52d1e380-rimg-w1024-h1536-dcf8f8f8-gmir?v=1792286935 ## 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 October in Chestertown](https://allevents.in/chestertown/live-music--october) - [Live Music Events in November in Chestertown](https://allevents.in/chestertown/live-music--november) ## FAQs - **Q**: What are the top Live Music events in Chestertown? - **A:** Dan Paisley & The Southern Grass (Sat Nov 14 2026 at 07:00 pm at Chestertown Volunteer Fire Co), 2026 Sultana Downrigging Festival Music Village Passes (Fri, 30 Oct at 03:00 pm at Chestertown Marina). - **Q**: What Live Music events are happening in Chestertown in October 2026? - **A:** 2026 Sultana Downrigging Festival Music Village Passes (Fri, 30 Oct at 03:00 pm at Chestertown Marina). - **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 Chestertown Volunteer Fire Co, Chestertown Marina. - **Q**: What is the price range for Live Music events in Chestertown? - **A:** Prices for Live Music events in Chestertown range from USD 28 to USD 65. 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 Volunteer Fire Company, Sultana Downrigging Festival Village. - **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 Rock Hall](https://allevents.in/rock-hall/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 Queenstown](https://allevents.in/queenstown-md/live-music)