# Festivals in Chestertown, MD 2026 | Culture & Street Fairs

- **Subtitle**: Your guide to festivals in Chestertown, Maryland 2026 — cultural celebrations, street fairs and food festivals. Find dates, locations and what to expect.
- **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 Chestertown. Be it a rocking music festival or scrumptious food festival in Chestertown, 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 Chestertown 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**: 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
  - **Interested Audience**:
    - Count: 1
  - **Date**: Fri Oct 30 2026 at 03:00 pm – Sun Nov 01 2026 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:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy8zNDdiNzE4ZmRkYmZiNDk4ZDRhNmYwMWIxMTFhYjBjODEyN2MwMTYzYzEzZWMxNTljODhhMWEwZWJlOGNmZTA2LXJpbWctdzEyMDAtaDgwMC1kY2YxZjNmMS1nbWlyLmpwZz92PTE3ODAzNTc1MzA.avif
  - **Price**: USD 28 to 55
  - **Categories**: fitness, Festivals, Nonprofit
- **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
  - **Date**: Sat Oct 31 2026 at 10:30 am – Sat Oct 31 2026 at 01:00 pm (-04:00)
  - **Event URL**: https://allevents.in/chestertown/2026-downrigging-tall-ship-sails-saturday-oct-31-morning-10-30am-1-00pm/100001990516999930
  - **Venue**: Chestertown Marina
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy9kZWEyZmI5ZDI5NDNlZDk3ZmRlZWNlNDQxNzczNmU0MTRjOGM5ZGFlNzEyMTY2ZTgzOWE3OTk4MDIyMTdjZGU4LXJpbWctdzEyMDAtaDgwMS1kYzYzOTJjMi1nbWlyLmpwZz92PTE3ODAzNTc1MTE.avif
  - **Price**: USD 49 to 71
  - **Categories**: fitness
- **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
  - **Interested Audience**:
    - Count: 3
  - **Date**: Fri Oct 30 2026 at 02:30 pm – Fri Oct 30 2026 at 05:00 pm (-04:00)
  - **Event URL**: https://allevents.in/chestertown/2026-downrigging-tall-ship-sails-friday-oct-30-2-30pm-5-00pm/100001990512808393
  - **Venue**: Chestertown Marina
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy9kZDNmMmJlNWM3N2ZmZjY0MzE0ZDBlZGM5MzQ2NmMyYzZjNGE2NWZjMjE3MDYyNGMxYzQ5ODdjODhkMDg1YTBkLXJpbWctdzEyMDAtaDgwMS1kYzYzOTJjMi1nbWlyLmpwZz92PTE3ODAzNTc1MDg.avif
  - **Price**: USD 49 to 71
  - **Categories**: fitness

## 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-dc083898-gmir?v=1788217417
- **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**: Grape Expectations: Brampton 1860 “Autumn in Full Swing: A Harvest Supper”
  - **Description**: Five harvest-inspired small-plate courses, with wine pairings, and Brampton 1860 sparkle in one unforgettable autumn supper event.About this EventWith autumn now in full swing, Brampton 1860 invites guests to settle into
  - **Venue**: 25227 Chestertown Rd
  - **Banner**: https://cdn-az.allevents.in/events2/banners/b39fe493842ef4e3e017d0a5539a46144b0f057f56c2f7184834b3d95ad0ec25-rimg-w1200-h800-dc080808-gmir.jpg?v=1787112197
- **Event Name**: Autism Family Fun & Resource Day
  - **Description**: Join Kay Services Inc. for a FREE afternoon of fun, connection, and resources for children and families in the autism community!
  - **Venue**: Kent County Public Library
  - **Banner**: https://cdn-az.allevents.in/events2/banners/6f39d887b9bdba76858bc4843a62373245540fd05bb82f9afd402067de4186e4-rimg-w1024-h1536-dcf8f8f8-gmir.jpg?v=1789979474
- **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**: Bat Chat & Guided Bat Walk
  - **Description**: Join the Town of Chestertown, Center for Environment & Society and the Maryland Department of Natural Resources for a free evening of bats!About this EventBat Chat & Guided Bat Walk
  - **Venue**: 300 Washington Ave
- **Event Name**: Bi-Monthly Bluegrass Jam
  - **Description**: Bring your instrument or voice and join us at the Harwood Nature Center. All abilities are welcome. If you can't play...just come listen!About this Event“Bluegrass has brought more people together and made more friends th
  - **Venue**: Lawrence Wetlands Preserve
  - **Banner**: https://cdn-az.allevents.in/events1/banners/4e59cfb4d542e1756859bbd0a1d044fb9f402f02440e19a15f3bdb998d842f13-rimg-w1200-h900-dca7aba4-gmir.jpg?v=1782866105
- **Event Name**: Ink & Indie 2026 - Author Signing Event
  - **Description**: We are bringing Ink & Indie back for a third year! We cannot wait for you to join us. 

Confirmed Authors:
Rebecca Wright
Jourdana Webber
Elsie bea
Erin Graves 
Jamie Fritz 
Jordana Blake
Megan michelle 
Taylor Colbert
Nicole crystal 
Genevieve Paul
C
  - **Venue**: The Bank
  - **Banner**: https://cdn-az.allevents.in/events10/banners/160e3ac4c5923c0d97a07e9a605b5b4764be513379cdc6081de9f17296921289-rimg-w500-h500-dcf8f8f8-gmir?v=1787714726

## 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 September in Chestertown](https://allevents.in/chestertown/festivals--september)
- [Festivals Events in October in Chestertown](https://allevents.in/chestertown/festivals--october)

## FAQs

- **Q**: What are the top Festivals events in Chestertown?
  - **A:** 2026 Sultana Downrigging Festival Music Village Passes (Fri Oct 30 2026 at 03:00 pm at Chestertown Marina), 2026 Downrigging Tall Ship Sails: SATURDAY OCT 31 (morning), 10:30am-1:00pm (Sat Oct 31 2026 at 10:30 am at Chestertown Marina), 2026 Downrigging Tall Ship Sails: FRIDAY OCT 30, 2:30pm-5:00pm (Fri Oct 30 2026 at 02:30 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 Chestertown Marina.
- **Q**: What is the price range for Festivals events in Chestertown?
  - **A:** Prices for Festivals events in Chestertown range from USD 28 to USD 71. 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 Sultana Downrigging Festival Village, Sultana Downrigging Tall Ship Sails.
- **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 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)