# Festivals in Chestertown, MD | Cultural Events & Fairs

- **Subtitle**: Explore upcoming festivals in  Chestertown, Maryland. Discover cultural celebrations, street fairs and seasonal events happening across the city. Join the festivities.
- **Category**: Festivals
- **Type**: category

## Audience

- **Followers**: 2.5M+
- **Recent Followers**: 
  - **Avatar 1**: https://cdn-az.allevents.in/events4/banners/c7a3bd77620a92a1fee77ed0b46cc305d65fcaf166695040aabebd480d9323a4-rimg-w200-h200-dc7e887a-gmir?v=1749580804
  - **Avatar 2**: https://cdn-az.allevents.in/events2/banners/87514fe09e2e42afe6f2e6b5b9e483315429bdfa0a64d2af3268e7f6798e263a-rimg-w200-h200-dc182a60-gmir?v=1760132405
  - **Avatar 3**: https://cdn-az.allevents.in/events4/banners/4372fbe0-97b1-11f0-925d-a7ce5707d3d8-rimg-w200-h200-dc445c46-gmir

## About

The best things to do in the world include attending top-notch festivals in [CITY]. Be it a rocking music festival or scrumptious food festival in [CITY], you will have a gala time of your life with a few of your close friends or your family. With the best of fun, entertainment, and food, the experience in festivals lets the enthusiasts immerse in the local culture and vibe. Ranging from the biggest outdoor beach parties to crazy music festivals, the festivals fall under various categories to suit everybody’s tastes. If you are looking for the best events and festivals in [CITY] listed on one platform - we have you covered.

Immerse yourself in the mega dance festivals, electrifying music festivals, theatre & film festivals, quirky local festivals and more with us!

## Festivals Events in Chestertown

- **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
  - **Interested Audience**:
    - Count: 82
  - **Date**: Sat May 23 2026 at 08:00 am – Sat May 23 2026 at 11:00 am (-04:00)
  - **Event URL**: https://allevents.in/chestertown/the-30th-annual-chestertown-tea-party-distance-classic-race-and-run-for-radcliffe-5k-and-10-mile-run/200029688645039
  - **Venue**: Wilmer Park
  - **Banner**: https://dyn-image.allevents.in/generate-image?v=4&title=The+30th+Annual+Chestertown+Tea+Party+Distance+Classic+Race+and+Run+for+Radcliffe+%285K+%26+10-Mile+Run%29&date=Sat+May+23+2026+at+08%3A00+am&bg=5
  - **Categories**: sports, parties, entertainment, festivals, trips-adventures, trekking
- **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
  - **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
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy9lZmMyY2Y4NTI1M2ZiYjlkOTVhNjc3YWM2NGZiMzNjYzJhY2RjYmJhYTkzZjExMGM2OWFkOTRiY2I2ZjA3MGI0LXJpbWctdzEwMDAtaDgwMS1kY2QzZDhkNi1nbWlyLmpwZz92PTE3NjkzNDY5ODk.avif
  - **Price**: USD 23 to 44
  - **Categories**: festivals, parties, entertainment
- **Event Name**: Schooner SULTANA Public Sails 2026-June
  - **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
  - **Date**: Fri Jun 26 2026 at 05:00 pm – Fri Jun 26 2026 at 07:00 pm (-04:00)
  - **Event URL**: https://allevents.in/chestertown/schooner-sultana-public-sails-2026-june/100001981439589150
  - **Venue**: Chestertown Marina
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy83N2MxODg0ZWZmMjEyZTk5N2JmZWE1ZTUwZGRmNDc2Nzc3OGEzNjcyNzE4NGEzYzgwODFjZmM0ZDRiMzZhMzYyLXJpbWctdzEwMDAtaDgwMS1kY2QzZDhkNi1nbWlyLmpwZz92PTE3NjkzNDY5ODc.avif
  - **Price**: USD 23 to 44
  - **Categories**: festivals, parties, entertainment
- **Event Name**: Schooner SULTANA Public Sails 2026-August
  - **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
  - **Date**: Fri Aug 14 2026 at 05:00 pm – Fri Aug 14 2026 at 07:00 pm (-04:00)
  - **Event URL**: https://allevents.in/chestertown/schooner-sultana-public-sails-2026-august/100001981440658348
  - **Venue**: Chestertown Marina
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy85NzUxOGQ0MGVkNmZhZTI3OGIxZmJjOGNhZTMzYzY0ZDg5MmJiMzliOGFmOWY3MTQwNTMyYjFjZDZlM2ZjNDJiLXJpbWctdzEwMDAtaDgwMS1kY2QzZDhkNi1nbWlyLmpwZz92PTE3NjkzNDY3MzQ.avif
  - **Price**: USD 23 to 44
  - **Categories**: festivals, parties, entertainment
- **Event Name**: Schooner SULTANA Public Sails 2026-September
  - **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
  - **Date**: Fri Sep 04 2026 at 05:00 pm – Sat Sep 19 2026 at 04:00 pm (-04:00)
  - **Event URL**: https://allevents.in/chestertown/schooner-sultana-public-sails-2026-september/100001981440775699
  - **Venue**: Chestertown Marina
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9mZDVkM2E5MDliOTcxNWE1NWY3ZjhkNWI0MmI2NzU2N2YyYjU4Mjk4MjU4YTRmZGI5OWM3NDMzYjU0ODRjZWUwLXJpbWctdzEwMDAtaDgwMS1kY2QzZDhkNi1nbWlyLmpwZz92PTE3NjkzNDY5MDY.avif
  - **Price**: USD 23 to 44
  - **Categories**: festivals, parties, entertainment
- **Event Name**: Schooner SULTANA Public Sails 2026-July
  - **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
  - **Date**: Fri Jul 24 2026 at 05:00 pm – Fri Jul 24 2026 at 07:00 pm (-04:00)
  - **Event URL**: https://allevents.in/chestertown/schooner-sultana-public-sails-2026-july/100001981440120740
  - **Venue**: Chestertown Marina
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy9hNTE4OWQ2ZDJjYjkyZmRmZWI2YjQ4YzM2ZWZiOWEwYTY4YWJjYzIzOWVkMGZkNzdhMzFlYzkxMjRiM2U0YWZmLXJpbWctdzEwMDAtaDgwMS1kY2QzZDhkNi1nbWlyLmpwZz92PTE3NjkzNDcxMzM.avif
  - **Price**: USD 23 to 44
  - **Categories**: festivals, parties, entertainment
- **Event Name**: WellFest at Wilmer -- A Community Wellness Event for the whole Kent County community!
  - **Description**: WellFest at Wilmer -- May 16 10am-2pm at Wilmer Park.  MARK YOUR CALENDARS for a day of fun exhibits, food and wellness-oriented festivities for the whole family!  Hosted by HomePorts, we're expecting a crowd and looking forward to celebrating all things
  - **Interested Audience**:
    - Count: 7
  - **Date**: Sat May 16 2026 at 10:00 am (-04:00)
  - **Event URL**: https://allevents.in/chestertown/wellfest-at-wilmer-a-community-wellness-event-for-the-whole-kent-county-community/200029874106411
  - **Venue**: Wilmer Park
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy82MDBlMmUxYmY1ODdiNDIxMjM2ODIwOWIwNWViOTAxY2JlNzA0Y2U0NzU1MDFkNjQ0OTdlNGFjNDczNzIzODU2LXJpbWctdzczNi1oMTAyNC1kY2ZlZmVmZi1nbWlyP3Y9MTc3NDgxNTczMQ.avif
  - **Categories**: health-wellness, calendar

## Trending Events in Chestertown

- **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=1774943361
- **Event Name**: The Spongebob Musical
  - **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/events2/banners/bf3bc9707e5257674f1440b50144c9e3541f48934b5790103b76fad32a2c22b9-rimg-w1200-h648-dc03182e-gmir.jpg?v=1773184415
- **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=1774815725
- **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**: 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**: 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
- **Event Name**: Rt 50 live at Rolph’s Wharf Sandbar!
  - **Description**: We are very excited to be back at Rolph’s Wharf!  Such a great spot!  Come by car, come by boat, come by seaplane!    Bring your friends, bring your family, bring your dog!  The next day is a holiday (Memorial day) so there’s no excuse not to come!
  - **Venue**: Rolph's Wharf Sandbar
  - **Banner**: https://cdn-az.allevents.in/events1/banners/4c00145c180c5d2223f4446c110ec47fd2ed16fca7e2bb9f6b70b86b3cb52824-rimg-w1170-h650-dcababa7-gmir?v=1774058387
- **Event Name**: Schooner SULTANA Public Sails 2026-June
  - **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/77c1884eff212e997bfea5e50ddf4767778a36727184a3c8081cfc4d4b36a362-rimg-w1000-h801-dcd3d8d6-gmir.jpg?v=1769346987

## Browse Festivals Events by Date

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

## FAQs

- **Q**: What are the top Festivals events in Chestertown?
  - **A:** The 30th Annual Chestertown Tea Party Distance Classic Race and Run for Radcliffe (5K & 10-Mile Run) (Sat May 23 2026 at 08:00 am at Wilmer Park), Schooner SULTANA Public Sails 2026-May (Sat May 02 2026 at 11:00 am at Chestertown Marina), Schooner SULTANA Public Sails 2026-June (Fri Jun 26 2026 at 05:00 pm at Chestertown Marina), Schooner SULTANA Public Sails 2026-August (Fri Aug 14 2026 at 05:00 pm at Chestertown Marina), Schooner SULTANA Public Sails 2026-September (Fri Sep 04 2026 at 05:00 pm at Chestertown Marina).
- **Q**: How can I find Festivals events in Chestertown?
  - **A:** You can discover upcoming Festivals 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 Festivals 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 Festivals events in Chestertown?
  - **A:** Some popular venues hosting Festivals events in Chestertown include Wilmer Park, Chestertown Marina.
- **Q**: What is the price range for Festivals events in Chestertown?
  - **A:** Prices for Festivals events in Chestertown range from USD 23 to USD 44. Many events also offer free entry.
- **Q**: Who are the top organizers for Festivals events in Chestertown?
  - **A:** Popular organizers hosting Festivals events in Chestertown include Radcliffe Creek School, Sultana Education Foundation Schooner SULTANA Public Sails, HomePorts, Inc..
- **Q**: Are there any online Festivals events available?
  - **A:** Yes, many Festivals 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 Festivals events in Chestertown?
  - **A:** Follow the Festivals category on AllEvents.in to get notified when new Festivals events are listed in Chestertown.

## Category Banner

- **Banner Image**: https://cdn2.allevents.in/transup/6e/5415e403f74b77938c0695ac11464e/Festival.jpg

## Festivals from nearby cities

- [Festivals in Worton](https://allevents.in/worton/festivals)
- [Festivals in Rock Hall](https://allevents.in/rock-hall/festivals)
- [Festivals in Sudlersville](https://allevents.in/sudlersville/festivals)
- [Festivals in Centreville](https://allevents.in/centreville-md/festivals)
- [Festivals in Galena](https://allevents.in/galena-md/festivals)
- [Festivals in Earleville](https://allevents.in/earleville/festivals)
- [Festivals in Queenstown](https://allevents.in/queenstown-md/festivals)
- [Festivals in Cecilton](https://allevents.in/cecilton/festivals)