# Events & Things To Do In Chestertown, MD This Weekend | May 1-3, 2026| AllEvents

- **Subtitle**: Chestertown, Maryland is a city full of experiences, activities and events. Explore some of the best things to do in Chestertown, Maryland this weekend and make your Friday, Saturday and Sunday full of fun and excitement.
- **Category**: Weekend
- **Display Name**: Events this weekend
- **Type**: time_filter

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## About

Weekends become special if you know how to make the most out of it. There are a lot of fun things to do and events in [CITY] this weekend for you to explore.

Make your weekends memorable. Check out all upcoming weekend events in [CITY].

## Weekend 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**: 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
  - **Interested Audience**:
    - Count: 1
  - **Date**: Sat May 02 2026 at 11:00 am – Sat May 23 2026 at 06:30 pm (-04:00)
  - **Event URL**: https://allevents.in/chestertown/schooner-sultana-public-sails-2026-may/100001981439368490
  - **Venue**: Chestertown Marina
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  - **Price**: USD 23 to 44
  - **Categories**: festivals, parties, entertainment
- **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
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  - **Price**: USD 18 to 29
  - **Categories**: Entertainment, Music, Parties
- **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

## 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 Weekend Events by Date

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

## FAQs

- **Q**: What are the top Weekend events in Chestertown?
  - **A:** 2026 Chestertown Pride Festival! (Sat May 02 2026 at 01:00 pm at 413 S Cross Street, 21620), Schooner SULTANA Public Sails 2026-May (Sat May 02 2026 at 11:00 am at Chestertown 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), 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 Weekend 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), Schooner SULTANA Public Sails 2026-May (Sat May 02 2026 at 11:00 am at Chestertown 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), 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 Weekend events in Chestertown?
  - **A:** You can discover upcoming Weekend 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 Weekend 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 Weekend events in Chestertown?
  - **A:** Some popular venues hosting Weekend events in Chestertown include 413 S Cross Street, 21620, Chestertown Marina, Garfield Center for the Arts at the Prince Theatre.
- **Q**: What is the price range for Weekend events in Chestertown?
  - **A:** Prices for Weekend events in Chestertown range from USD 18 to USD 44. Many events also offer free entry.
- **Q**: Who are the top organizers for Weekend events in Chestertown?
  - **A:** Popular organizers hosting Weekend events in Chestertown include Chestertown Pride Festival, Sultana Education Foundation Schooner SULTANA Public Sails, Garfield Center for the Arts.
- **Q**: Are there any online Weekend events available?
  - **A:** Yes, many Weekend 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 Weekend events in Chestertown?
  - **A:** Follow the Weekend category on AllEvents.in to get notified when new Weekend events are listed in Chestertown.

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