# Music Events in Chestertown, MD 2026 | Concerts & Live Music

- **Subtitle**: Discover upcoming music events in Chestertown, Maryland. Book tickets for concerts, live gigs, music festivals and performances happening across the city.
- **Category**: Music
- **Display Name**: Music events
- **Type**: category

## Audience

- **Followers**: 3.7M+
- **Recent Followers**: 
  - **Avatar 1**: https://cdn-az.allevents.in/events1/banners/4509d850-a0a0-11f0-9831-97f1094caa3d-rimg-w200-h200-dcaf6773-gmir
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## 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
- **Event Name**: Let Love Win RnB Festival
  - **Description**: Let Love Win RnB Festival is a unique outdoor day party experience for a mature 30+ crowd who love great music, good energy, and VIBES‼️About this Event🎶 Let Love Win RnB Festival 🎶 A Grown & Sexy Outdoor Experience L
  - **Date**: Sat, 27 Jun at 11:00 am – Sat, 27 Jun at 07:00 pm (-04:00)
  - **Event URL**: https://allevents.in/middletown/let-love-win-rnb-festival/100001986277232672
  - **Venue**: Smokin Hoofs Farm
  - **Banner**: https://cdn2.allevents.in/transup/ee/84e07e9022479dbc8582fce47ccfbe/featuring-31-.png
  - **Price**: min: 33.85, max: 215.26, currency: USD
  - **Categories**: festivals, entertainment, parties, performances, art, theatre

## About

Music signifies the vibrant energy of the place! Such music events in [CITY] make the city alive throughout the year. From live music shows and concerts to karaoke nights and gigs at bars and cafes, music fills the silence beautifully in [CITY]. The city has a lot for you in store, and there isn’t any lack of music events in [CITY] for classical lovers or concertgoers! Music is here to heal you and make you groove with festivals and heartfelt concerts in [CITY]. Explore such music events happening near you with us and get in the groove to set the stage on fire.

## 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**: 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**: 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
  - **Date**: Fri May 01 2026 at 07:00 pm – Sun May 17 2026 at 04:00 pm (-04:00)
  - **Event URL**: https://allevents.in/chestertown/gca-presents-the-spongebob-musical-new-dates/100001985834808369
  - **Venue**: Garfield Center for the Arts at the Prince Theatre
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9mMzE2ODc3YzJhNTlhZmI0MzJmYWQ5YTdjMTNiMDY0NGY3MzU2OWZkMDI3ZWY3ZjEwOGJhN2EzNzAzZmFlNzRiLXJpbWctdzEyMDAtaDY0OC1kYzAzMTgyZS1nbWlyLmpwZz92PTE3NzQzODE5NjE.avif
  - **Price**: USD 18 to 29
  - **Categories**: Entertainment, Music, Parties
- **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
  - **Date**: Sat May 09 2026 at 06:00 pm – Sat May 09 2026 at 11:00 pm (-04:00)
  - **Event URL**: https://allevents.in/chestertown/sultanas-annual-gala-may-9-2026/100001981450487748
  - **Venue**: Clovelly Farm
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy9lOGNhYjc2YmUxMDg2OGI2YzhiNzE0MTcxNGE4OTg5ZjgyYzg2OTY4NTFlYzg3YzI5Zjk0MmQ1YjY0YmUyYjFjLXJpbWctdzEyMDAtaDgyNS1kYzE5MTgxNy1nbWlyLmpwZz92PTE3NjkzNDY4MTc.avif
  - **Price**: USD 200
  - **Categories**: nonprofit, parties, live-music, entertainment
- **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**: 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**: 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
- **Event Name**: Memorial Day Jam at the Sandbar
  - **Description**: Just when you thought we moved our beat, we're back at the Sandbar for at least one more patrol in the original band's stomping grounds. This will be new for Nick and Darren, but the Sandbar is still one of Sheriff Keith's favorite hangouts and the staff
  - **Interested Audience**:
    - Count: 14
  - **Date**: Mon May 25 2026 at 03:00 pm – Mon May 25 2026 at 06:00 pm (-04:00)
  - **Event URL**: https://allevents.in/chestertown/memorial-day-jam-at-the-sandbar/200029974750634
  - **Venue**: ROLPHS WHARF MARINA
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy82NzA5NGNhZmMwMGE0YTVlZGRiMmIxZGEzMjFiY2Q0ODQwOTgxNzJiYTkzMDNhZjkwOGRhMTgxYjUyMzI0ZDdlLXJpbWctdzc4NS1oNzc5LWRjMTcxODFjLWdtaXI_dj0xNzc2ODk5MDc0.avif
  - **Categories**: music, entertainment, memorial-day
- **Event Name**: Experience the Bay with Chesapeake Scenes
  - **Description**: Join us at the Nature Center in the LWP as we close out the first session of Sultana’s Community Classroom with Chesapeake ScenesAbout this EventJoin us at the Harwood Nature Center in the Lawrence Wetlands Preserve as we
  - **Date**: Fri May 15 2026 at 07:00 pm – Fri May 15 2026 at 08:30 pm (-04:00)
  - **Event URL**: https://allevents.in/chestertown/experience-the-bay-with-chesapeake-scenes/100001981791421490
  - **Venue**: Lawrence Wetlands Preserve
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy9lYWJhMGM0NDA4ZWVmNGUxZmRiYWZmYzA1YzM3NTUwMGFiNDEzZTFmNDk4MzgxNDBkZGNkMzg4NDAxMWNmMmJhLXJpbWctdzQ4MC1oMjUyLWRjYmJhNzkwLWdtaXIuanBnP3Y9MTc2OTkyMzAzMw.avif
  - **Price**: Free
  - **Categories**: art
- **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-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 Music Events by Date

- [Music Events Today in Chestertown](https://allevents.in/chestertown/music--today)
- [Music Events This Weekend in Chestertown](https://allevents.in/chestertown/music--this-weekend)
- [Music Events in April in Chestertown](https://allevents.in/chestertown/music--april)
- [Music Events in May in Chestertown](https://allevents.in/chestertown/music--may)

## FAQs

- **Q**: What are the top Music events in Chestertown?
  - **A:** 2026 Chestertown Pride Festival! (Sat May 02 2026 at 01:00 pm at 413 S Cross Street, 21620), 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), GCA Presents "The Spongebob Musical" NEW DATES (Fri May 01 2026 at 07:00 pm at Garfield Center for the Arts at the Prince Theatre), Sultana's Annual Gala, May 9, 2026 (Sat May 09 2026 at 06:00 pm at Clovelly Farm), 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).
- **Q**: What are the top free Music events in Chestertown?
  - **A:** Experience the Bay with Chesapeake Scenes (Fri May 15 2026 at 07:00 pm at Lawrence Wetlands Preserve).
- **Q**: What 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), GCA Presents "The Spongebob Musical" NEW DATES (Fri May 01 2026 at 07:00 pm at Garfield Center for the Arts at the Prince Theatre).
- **Q**: How can I find Music events in Chestertown?
  - **A:** You can discover upcoming 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 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 Music events in Chestertown?
  - **A:** Some popular venues hosting Music events in Chestertown include 413 S Cross Street, 21620, The Shanty Beach Bar at Tolchester Marina, Garfield Center for the Arts at the Prince Theatre.
- **Q**: What is the price range for Music events in Chestertown?
  - **A:** Prices for Music events in Chestertown range from USD 18 to USD 215. Many events also offer free entry.
- **Q**: Who are the top organizers for Music events in Chestertown?
  - **A:** Popular organizers hosting Music events in Chestertown include Chestertown Pride Festival, Love Hate Mixtape, Garfield Center for the Arts.
- **Q**: What types of Music events can I find in Chestertown?
  - **A:** You can explore a variety of music sub-genres and styles including Hip Hop Music, House Music, Classical Music, Afrobeats, Bachata and more.
- **Q**: Are there any online Music events available?
  - **A:** Yes, many 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 Music events in Chestertown?
  - **A:** Follow the Music category on AllEvents.in to get notified when new Music events are listed in Chestertown.

## Category Banner

- **Banner Image**: https://cdn2.allevents.in/transup/7d/3b7eda185942c291f6c4d1b664725c/music.png

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