# All Events in Chestertown

- **City**: Chestertown
- **State**: Maryland
- **Country**: United States
- **Continent**: North America
- **Timezone**: -05:00
- **Currency**: USD
- **Banner**: https://cdn2.allevents.in/transup/4a/3eb947ce48417e9f724bc0a3c8a200/USA-default.webp

## Featured Events in Chestertown

- **Event Name**: 30th & Final Chestertown Jazz Festival
  - **Description**: Celebrating 30 Years of Extraordinary Jazz By The RiverAbout this EventCome celebrate 30 years of music by the river with us in Wilmer Park for the 30th & Final Chestertown Jazz Festival
  - **Date**: Sat, 12 Sep at 12:00 pm – Sat, 12 Sep at 06:00 pm (-04:00)
  - **Event URL**: https://allevents.in/chestertown/30th-and-final-chestertown-jazz-festival/100001993930984249
  - **Venue**: Wilmer Park
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:600:300/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy80YzVkN2Y5YzE3OTMyZTcxYzYyNzVmMDc1YjY1ODYzNzdjOGJjYjQ0YjE0YzVmNjQ4NWQ0ZWZkMDQ4OWFlYWNjLXJpbWctdzEyMDAtaDY3NS1kYzAzMTMyYy1nbWlyLmpwZz92PTE3ODQwODUzNTI.avif
  - **Price**: min: 44.52, max: 44.52, currency: USD
  - **Categories**: fitness, Entertainment, Music, Festivals
- **Event Name**: Bead Society Class:  “Happy Summer Jewelry Medley"
  - **Description**: When you must spend more for your daily essentials like groceries and gasoline, we want to save you money for your jewelriesAND have a good fortune to increase your cash flow!This is a quick and easy bracelet and cell phone charm set you
  - **Date**: Sat, 22 Aug at 02:30 pm – Sat, 22 Aug at 05:00 pm (-05:00)
  - **Event URL**: https://allevents.in/wilmington/bead-society-class-happy-summer-jewelry-medley-tickets/80002159652884
  - **Venue**: Wellness Plus Delaware
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:600:300/g:sm/sh:100/aHR0cHM6Ly9jZG4yLmFsbGV2ZW50cy5pbi90aHVtYnMvdGh1bWI2YTY5MDU2ZGQ5NDEzLmpwZw.avif
  - **Price**: min: 35, max: 35, currency: USD
  - **Categories**: workshops, health-wellness, shopping
- **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, 04 Sep at 05:00 pm – Sat, 19 Sep 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:600:300/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9mZDVkM2E5MDliOTcxNWE1NWY3ZjhkNWI0MmI2NzU2N2YyYjU4Mjk4MjU4YTRmZGI5OWM3NDMzYjU0ODRjZWUwLXJpbWctdzEwMDAtaDgwMS1kY2QzZDhkNi1nbWlyLmpwZz92PTE3NjkzNDY5MDY.avif
  - **Price**: min: 22.79, max: 43.99, currency: USD
  - **Categories**: fitness, Festivals
- **Event Name**: CrimeStery Fest 2026
  - **Description**: CrimeStery-Fest 2026 — All Things Crime and MysteryThe Northeast's Coolest Crime Convention!Calling all true crime enthusiasts, CrimeStery-Fest returns for an immersive three-day celebration
  - **Date**: Fri, 09 Oct at 04:00 pm – Sun, 11 Oct at 04:00 pm (-05:00)
  - **Event URL**: https://allevents.in/danvers/crimestery-fest-2026-tickets/80005231957486
  - **Venue**: DoubleTree by Hilton Hotel Boston North Shore, Ferncroft Road, Danvers, MA, USA
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:600:300/g:sm/sh:100/aHR0cHM6Ly9jZG4yLmFsbGV2ZW50cy5pbi90aHVtYnMvdGh1bWI2OWY4MmM1YjU5MDBmLmpwZw.avif
  - **Price**: min: 30, max: 90, currency: USD
  - **Categories**: exhibitions, conferences, festivals, art, literary-art, entertainment, business, parties, music, food-drinks, comedy

## Chestertown's Most-Loved

### Events Categories

- [Music (24 events)](https://allevents.in/chestertown/music)
- [Parties (25 events)](https://allevents.in/chestertown/parties)
- [Food & Drinks (21 events)](https://allevents.in/chestertown/food-drinks)
- [Festivals (21 events)](https://allevents.in/chestertown/festivals)
- [Fine Arts (13 events)](https://allevents.in/chestertown/fine-arts)
- [Health & Wellness (9 events)](https://allevents.in/chestertown/health-wellness)
- [Kids (20 events)](https://allevents.in/chestertown/kids)
- [Trips & Adventure (18 events)](https://allevents.in/chestertown/trips-adventures)
- [Sports (4 events)](https://allevents.in/chestertown/sports)
- [Photography (3 events)](https://allevents.in/chestertown/photography)
- [Comedy (3 events)](https://allevents.in/chestertown/comedy)
- [Cooking (3 events)](https://allevents.in/chestertown/cooking)
- [Theatre (3 events)](https://allevents.in/chestertown/theatre)
- [Performances (1 events)](https://allevents.in/chestertown/performances)
- [Crafts (1 events)](https://allevents.in/chestertown/crafts)
- [Dance (1 events)](https://allevents.in/chestertown/dance)

## Popular Events in Chestertown

- **Event Name**: 30th & Final Chestertown Jazz Festival
  - **Description**: Celebrating 30 Years of Extraordinary Jazz By The RiverAbout this EventCome celebrate 30 years of music by the river with us in Wilmer Park for the 30th & Final Chestertown Jazz Festival
  - **Interested Audience**:
    - Count: 3
  - **Date**: Sat, 12 Sep at 12:00 pm – Sat, 12 Sep at 06:00 pm (-04:00)
  - **Event URL**: https://allevents.in/chestertown/30th-and-final-chestertown-jazz-festival/100001993930984249
  - **Venue**: Wilmer Park
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy80YzVkN2Y5YzE3OTMyZTcxYzYyNzVmMDc1YjY1ODYzNzdjOGJjYjQ0YjE0YzVmNjQ4NWQ0ZWZkMDQ4OWFlYWNjLXJpbWctdzEyMDAtaDY3NS1kYzAzMTMyYy1nbWlyLmpwZz92PTE3ODQwODUzNTI.avif
  - **Price**: USD 45
  - **Categories**: fitness, Entertainment, Music, Festivals
- **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, 04 Sep at 05:00 pm – Sat, 19 Sep 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**: fitness, Festivals
- **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
  - **Date**: Sun, 01 Nov at 01:00 pm – Sun, 01 Nov at 03:30 pm (-05:00)
  - **Event URL**: https://allevents.in/chestertown/2026-downrigging-tall-ship-sails-sunday-nov-1-1-00pm-3-30pm/100001990518897606
  - **Venue**: Chestertown Marina
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy82NmNkNjJiYTcwMWJjNDA3MWNkNjhjODdmY2RlZDdmNmJjYmI5YmYzM2NmZTgzNDRhYzczNDIxYzMzNTRjNDM1LXJpbWctdzEyMDAtaDgwMS1kYzYzOTJjMi1nbWlyLmpwZz92PTE3ODAzNTc1MzI.avif
  - **Price**: USD 49 to 71
  - **Categories**: fitness
- **Event Name**: Grape Expectations: Brampton 1860 “Harvest Afterglow: A Late Summer Supper”
  - **Description**: Five harvest-inspired small-plate courses, with wine pairings, and Brampton 1860 sparkle in one unforgettable late-summer supper event.About this EventAs the season turns, Brampton 1860 invites guests to savor that golden
  - **Date**: Thu, 17 Sep at 06:00 pm – Thu, 17 Sep at 08:00 pm (-04:00)
  - **Event URL**: https://allevents.in/chestertown/grape-expectations-brampton-1860-harvest-afterglow-a-late-summer-supper/100001998129366724
  - **Venue**: 25227 Chestertown Rd
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy9iMzlmZTQ5Mzg0MmVmNGUzZTAxN2QwYTU1MzlhNDYxNDRiMGYwNTdmNTZjMmY3MTg0ODM0YjNkOTVhZDBlYzI1LXJpbWctdzEyMDAtaDgwMC1kYzA4MDgwOC1nbWlyLmpwZz92PTE3ODcxMTIxOTc.avif
  - **Price**: USD 98
  - **Categories**: workshops
- **Event Name**: Mooday's Music, LLC Open House
  - **Description**: 🎉 You're Invited to the Mooday’s Music, LLC Open House! 🎶

Come celebrate with us on Saturday, August 29th from 9:00 AM–12:00 PM for a morning full of music, fun, and community!

✨ FREE ADMISSION!
Enjoy:
🎵 Free music classes
🎨 Face painting
🏰 Moon bounce
  - **Interested Audience**:
    - Count: 118
  - **Date**: Sat, 29 Aug at 09:00 am (-04:00)
  - **Event URL**: https://allevents.in/chestertown/moodays-music-llc-open-house/200030246062743
  - **Venue**: 115 S Lynchburg St, Suite D, Chestertown, MD, United States, Maryland 21620
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy8zMWIwN2UyYjE5NDk5MTVlNDQ4YzIwN2ZmMGU3ODM3ZjE5YzYwYWU1NmI1NzUxNWRjYTNmZDEyYWI2YjBhZTBiLXJpbWctdzEyMDAtaDE1NTMtZGNmOGY4ZjgtZ21pcj92PTE3ODcwNDI3Nzg.avif
  - **Categories**: workshops, music, food-drinks, art, fine-arts, trips-adventures, entertainment
- **Event Name**: Oysters and Indians Public Paddle - 2026 - Sultana Education Foundation
  - **Description**: Explore the remnants of ancient Indian settlements while paddling along the unspoiled, forested shorelines of Still Pond Creek.About this EventExplore the remnants of ancient Indian settlements while paddling along the un
  - **Date**: Sat, 19 Sep at 10:00 am – Sat, 19 Sep at 12:30 pm (-04:00)
  - **Event URL**: https://allevents.in/chestertown/oysters-and-indians-public-paddle-2026-sultana-education-foundation/100001978425897116
  - **Venue**: Stillpond Creek
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy9mMWUwMGU2NTAzMjgzODM3MTMyOTkxOTRhNDNmYTQ0MTQ1N2I0OTVjNTE1OWIxODE0N2MxYzJlM2NiZmY1MDYzLXJpbWctdzQyMi1oNzY0LWRjZjVlYmQ1LWdtaXIuanBnP3Y9MTc2ODA1MjY3Mg.avif
  - **Price**: USD 12 to 49
  - **Categories**: fitness, trips-adventures
- **Event Name**: Rt 50 live at Rolph’s Wharf Sandbar!
  - **Description**: We are very happy to be back at Rolph’s wharf Sandbar!  Bring your friends, bring your family, bring your dog!    Also, bring your bathing suit. They have a nice beach and a swimming pool.
  - **Interested Audience**:
    - Count: 38
  - **Date**: Sat, 29 Aug at 02:00 pm – Sat, 29 Aug at 06:00 pm (-04:00)
  - **Event URL**: https://allevents.in/chestertown/rt-50-live-at-rolphs-wharf-sandbar/200030423910945
  - **Venue**: ROLPHS WHARF MARINA
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9iNzA1OWI5OTFlOGZjYzE1MzlhOWVlMjk5MjBmYjI2ZDNkMmI1ZjI5YWM2OWNhY2U4NGIyMDQxYmY3YjFjYTI3LXJpbWctdzExNzAtaDY1MC1kY2E4YThhOC1nbWlyP3Y9MTc4NzIwMjc3Nw.avif
  - **Categories**: sports, dog
- **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, 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:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy8zNDdiNzE4ZmRkYmZiNDk4ZDRhNmYwMWIxMTFhYjBjODEyN2MwMTYzYzEzZWMxNTljODhhMWEwZWJlOGNmZTA2LXJpbWctdzEyMDAtaDgwMC1kY2YxZjNmMS1nbWlyLmpwZz92PTE3ODAzNTc1MzA.avif
  - **Price**: USD 28 to 55
  - **Categories**: fitness, Festivals, Nonprofit
- **Event Name**: Rhythm & Vines Festival
  - **Description**: We’re unveiling our Nature Sacred Space with a ribbon cutting ceremony at NOON. 

We’ve also been included as a stop on “The little yellow journal tour”, which is a cross-country celebration by Nature Sacred marking their 30th anniversary. 

Our host for
  - **Interested Audience**:
    - Count: 136
  - **Date**: Sat, 29 Aug at 12:00 pm (-04:00)
  - **Event URL**: https://allevents.in/chestertown/rhythm-and-vines-festival/200030407393325
  - **Venue**: 9155 American Legion Rd, Chestertown, MD, United States, Maryland 21620
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEwL2Jhbm5lcnMvY2Q5YzhkZDY3NTllOTA5NGQ5ZDY0YzkzZTIzYTFjNzBjNGVhODc5MTUxMzc0ZTU5NzY5ZGE0ZGI3NThmZmRmYy1yaW1nLXcxMDgwLWgxMzUwLWRjMDg0ODI4LWdtaXI_dj0xNzg2NzUzOTE2.avif
  - **Categories**: entertainment, festivals, music, comedy, nonprofit, parties, reggae
- **Event Name**: 2026 BBQ and Brews
  - **Description**: Get ready for a chill time at the 2026 BBQ and Brews event - good food, cold drinks, and great vibes all around!About this Event2026 BBQ and BrewsCome join us for a finger-lickin'
  - **Date**: Sat, 05 Sep at 12:00 pm – Sat, 05 Sep at 05:00 pm (-04:00)
  - **Event URL**: https://allevents.in/chestertown/2026-bbq-and-brews/100001980626961559
  - **Venue**: 7281 Wilkins Ln
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9mN2Q2YjZhNTBlYmZlNjk5MzU2OGJlNTU2ZjhhY2I1YjdiZTA3YWJhNDk4MjM0YTgzYmQ0YmU0NGFkMWFhNWFkLXJpbWctdzEyMDAtaDE2MDEtZGNmZWZlZmUtZ21pci5qcGc_dj0xNzgyNzU3MTQ4.avif
  - **Price**: USD 29 to 45
  - **Categories**: fitness, Music, Entertainment
- **Event Name**: Kids' Night (Ages 2-12)
  - **Description**: Parents, are you looking for affordable child care so you can have a night out? Looking for a fun, enriching environment for your kids to go?
$20 for 1 child | $35 for 2 | $50 for 3
Ages 2-12
  - **Date**: Sat, 22 Aug at 05:00 pm – Sat, 22 Aug at 07:30 pm (-04:00)
  - **Event URL**: https://allevents.in/chestertown/kids-night-ages-2-12/200030576717842
  - **Venue**: 115 S Lynchburg St, Suite D, Chestertown, MD, United States, Maryland 21620
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy80MTI4NjgyYjA1NTViOWVjNTIyNDc0MmExYzY1MzE1OTI4NGIxNDdkZmE0NDY2NGNjNjc5ZWFhYTgzMTNmZjYzLXJpbWctdzEyMDAtaDE1NTMtZGNmOGY4ZjgtZ21pcj92PTE3ODcwNDM5NDI.avif
  - **Categories**: Kids
- **Event Name**: Kent County 911 Communications Center Tour
  - **Description**: Register Here:
https://www.signupgenius.com/go/10C0445ABAC23A2FEC70-64608516-kent

Ever wondered what happens when someone calls 911?

Join us for a behind-the-scenes visit to the Kent County 911 Communications Center! We will learn how emergency dispatch
  - **Interested Audience**:
    - Count: 39
  - **Date**: Thu, 01 Oct at 11:00 am (-04:00)
  - **Event URL**: https://allevents.in/chestertown/kent-county-911-communications-center-tour/200030311525639
  - **Venue**: 104 Vickers Dr, Unit D Chestertown, MD 21620-3327, United States
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy82ODg5NzY1MzE2OWQ2YzA1ZjhkYjVmYTVlYjQ2M2QyZDI1Nzk2YWFiMmUwMTI0MWVkNTBkY2FjMGNhZWI1NmViLXJpbWctdzEyMDAtaDUwMC1kYzA4MDgwOC1nbWlyP3Y9MTc4NzMyMTcyNQ.avif
- **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
  - **Date**: Sat, 31 Oct at 02:30 pm – Sat, 31 Oct at 05:00 pm (-04:00)
  - **Event URL**: https://allevents.in/chestertown/2026-downrigging-tall-ship-sails-saturday-oct-31-afternoon2-30pm-5-00pm/100001990518240641
  - **Venue**: Chestertown Marina
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy80YzQxNzQwNTAyYmI2MWNmZWI0YzIwZjNhMmFkMDY1MTM5MDE3Y2VjMmE4ZDQ4OWU4ZmQ3YzQ4N2MwNDQ5ZjA0LXJpbWctdzEyMDAtaDgwMS1kYzYzOTJjMi1nbWlyLmpwZz92PTE3ODAzNTc1MjA.avif
  - **Price**: USD 45 to 71
  - **Categories**: fitness
- **Event Name**: Fall Homeschool Karate Classes
  - **Description**: 6-Week Program: 1-Day/week for 6-weeks
-	Chestertown Location: Tuesdays September 8 through October 13 - DM or Call/Text 410-708-9944 for details
o	12:30 PM – Tiny Tigers ages 3-6 years old
o	1:00 PM – Youth/Teen ages 6 to 15 years old
-	Easton Location:
  - **Interested Audience**:
    - Count: 15
  - **Date**: Tue, 08 Sep at 12:30 pm (-04:00)
  - **Event URL**: https://allevents.in/chestertown/fall-homeschool-karate-classes/200030291235713
  - **Venue**: 903 Washington Ave., Suite # 3, Chestertown, MD, United States, Maryland 21620
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9hNjc4NTJkZTdkMTM4NjZhNzNkZWEyZDk2MmMzNjdhMGNmMGYxMDQ3MjkyMDczNWYxOWMxNDQ2YjMzZTVhOWNjLXJpbWctdzEyMDAtaDE4MDAtZGNmOGY4ZjgtZ21pcj92PTE3ODcyMzI1MTE.avif
  - **Categories**: workshops, health-wellness, meditation, calendar
- **Event Name**: Grief Discussions
  - **Description**: Grief can be a difficult journey, but it can also be helpful to connect with others who understand. Join us for **Grief Discussions**, a monthly book club and conversation group hosted by Fellows, Helfenbein & Newnam Funeral Home.

Each meeting is cen
  - **Interested Audience**:
    - Count: 32
  - **Date**: Wed, 26 Aug at 06:00 pm (-04:00)
  - **Event URL**: https://allevents.in/chestertown/grief-discussions/200030291257742
  - **Venue**: 130 Speer Rd, Chestertown, MD 21620-1037, United States
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy81N2U2Mjk5MzMyMWRhNWNiY2Q3OWZmMDcwZjQxMzUzZWNlM2U3MjExNGI0ZTI5OGRlYzY1MGNjMTUwOGI4ZWZkLXJpbWctdzEyMDAtaDYyOC1kY2Y4ZjhmOC1nbWlyP3Y9MTc4NzIzMjUxMg.avif
  - **Categories**: meetups
- **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, 30 Oct at 02:30 pm – Fri, 30 Oct 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
- **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, 31 Oct at 10:30 am – Sat, 31 Oct 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**: 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
  - **Date**: Sun, 25 Oct at 10:00 am – Sun, 25 Oct at 12:30 pm (-04:00)
  - **Event URL**: https://allevents.in/chestertown/waterfowl-and-foliage-public-paddle-2026-sultana-education-foundation/100001978426038539
  - **Venue**: Rileys Mill Landing
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy8yYjkzZmYyMmM1YzFhN2YwYTk1MjJhMGI1MjFlZmFiZDY0NDdmZWI1MTliY2FhMzYzMTg0MGVkZjcyZTUwNTFhLXJpbWctdzEyMDAtaDY3NS1kYzE5MWExNS1nbWlyLmpwZz92PTE3NjgwNTI2NzA.avif
  - **Price**: USD 12 to 49
  - **Categories**: fitness, trips-adventures

## Browse Events in Chestertown by Date

- [Events Today in Chestertown](https://allevents.in/chestertown/today)
- [Events This Weekend in Chestertown](https://allevents.in/chestertown/this-weekend)
- [Events in August 2026 in Chestertown](https://allevents.in/chestertown/august)
- [Events in September 2026 in Chestertown](https://allevents.in/chestertown/september)

## Moments from Events in Chestertown

- **Review**: "An outstanding evening filled with great energy, meaningful conversations and valuable new introductions! Slappey & Sadd and J. Franklin Burns, P.C. continued a wonderful Atlanta legal-community tradition, and Buckhead Wine Brats was proud to help bring quality people together—because one great introduction can change everything. Join Buckhead Wine Brats Interest List click Below: 
https://buckheadwinebrats.com/join-bwb-interest-list/"
  - **Rating**: 5/5
  - **By**: paul oliva
  - **Event**: Late Summer Lawyers Party: With the Buckhead Wine Brats-Hosted by Slappey & Sadd & J. Franklin Burns at Hudson Grille Sandy Springs, Roswell Road Northeast, Sandy Springs, GA, USA
  - **Date**: 2026-08-21 18:33:55
  - **Photo**: https://cdn2.allevents.in/transup/e9/0bd3e201e540e6937117352b64c8cd/images/LawyersPartyPhoto777356939_10216768279915847_8079531256632714731_n.webp
  - **User Avatar**: https://www.gravatar.com/avatar/27161d8c8828a4b8873ff95248e84665?s=800&d=identicon&r=g
- **Review**: "it was an exciting time this year and you could feel God's presence move through the crowd!"
  - **Rating**: 5/5
  - **By**: Jeremy DeGroat
  - **Event**: Unity Christian Music Festival at Heritage Landing
  - **Date**: 2026-08-21 14:16:07
  - **Photo**: https://cdn2.allevents.in/transup/4a/cf42c2c1234d0dac3d7125bb5dc9ab/images/20260806_130537-0-.webp
  - **User Avatar**: https://cdn-az.allevents.in/events6/banners/ebd9b31e8d683a374547c3a96b82ca4c51687eb96ec74e8fc2db51a177744643-rimg-w200-h200-dcd4d9d8-gmir?v=1758424806
- **Review**: "An outstanding evening filled with great energy, meaningful conversations and valuable new introductions! Slappey & Sadd and J. Franklin Burns, P.C. continued a wonderful Atlanta legal-community tradition, and Buckhead Wine Brats was proud to help bring quality people together—because one great introduction can change everything. Join Buckhead Wine Brats Interest List click Below: 
https://buckheadwinebrats.com/join-bwb-interest-list/"
  - **Rating**: 5/5
  - **By**: paul oliva
  - **Event**: Late Summer Lawyers Party: With the Buckhead Wine Brats-Hosted by Slappey & Sadd & J. Franklin Burns at Hudson Grille Sandy Springs, Roswell Road Northeast, Sandy Springs, GA, USA
  - **Date**: 2026-08-21 18:25:16
  - **User Avatar**: https://www.gravatar.com/avatar/27161d8c8828a4b8873ff95248e84665?s=800&d=identicon&r=g
- **Review**: "It was a well planned/organized event. The Gelati truck was delicious!! Thanks to DTSB for paying for the 1st 200. The self guided tour of Union Station was interesting. Great possible development projects for Downtown. Let’s restore the past and not tear everything down to build more apartments/condos."
  - **Rating**: 5/5
  - **By**: J E
  - **Event**: America250 Hometown Whistle Stop Tour by Canadian National Railway at Union Station (South Bend, Indiana)
  - **Date**: 2026-08-20 21:13:51
  - **Photo**: https://cdn2.allevents.in/transup/86/3a0e0039d043b78c539004fa2ffb89/images/IMG_7687.webp
  - **User Avatar**: https://lh3.googleusercontent.com/a/ACg8ocKwoY4gfWM0CAOWOtyOtmlVQu8Q_Bf1POuQjXUOIVtC9pBUvw=s96-c?sz=200
- **Review**: "Great show"
  - **Rating**: 5/5
  - **By**: john lofano
  - **Event**: Men At Work  Toad The Wet Sprocket & Shonen Knife at Silver Legacy Casino
  - **Date**: 2026-08-19 17:03:16
  - **Photo**: https://cdn2.allevents.in/transup/8c/4f996fc28f4356a1d18827516fe822/images/IMG_4113.webp
  - **User Avatar**: https://www.gravatar.com/avatar/27161d8c8828a4b8873ff95248e84665?s=800&d=identicon&r=g
- **Review**: "Family fun, fabulous MUSIC, food, beer and polka DANCING with Papa!!!"
  - **Rating**: 5/5
  - **By**: Sandra Kennedy
  - **Event**: SugRRocK Full Band at Germanfest Picnic in Dayton at Dayton Liederkranz Turner German Club
  - **Date**: 2026-08-19 02:50:32
  - **Photo**: https://cdn2.allevents.in/transup/2b/3c1236a9b144c68c6d3296f5b46f19/images/8dd4a8169965d34b02da862bac89b105aa659db6705fd9070bb2c511d1b4876b_exif.webp
  - **User Avatar**: https://www.gravatar.com/avatar/e344e858bc1b2d78af85d06ca18ec77f?s=800&d=identicon&r=g
- **Review**: "A fun time was had by all. The music and location were beautiful.  Ocean breeze and melodies!"
  - **Rating**: 5/5
  - **By**: Denise Lee
  - **Event**: The Encore Band at The Sanctuary Hotel 6pm at The Sanctuary at Kiawah Island Golf Resort
  - **Date**: 2026-08-18 14:19:02
  - **Photo**: https://cdn2.allevents.in/transup/c7/5ab5156dd44166befcb7bc6623d267/images/20260815_192923.webp
  - **User Avatar**: https://lh3.googleusercontent.com/a/ACg8ocLbSl_W1C_d0me6YBm6bJxM8UyrYAB6U0yCAzVl3VRk7bnlng=s96-c?sz=200
- **Review**: "it was a fun evening .  The poetry haiku’s were more humorous and a bit nasty. lol"
  - **Rating**: 4/5
  - **By**: TheSongoftheheart
  - **Event**: AUGUST POETRY NIGHT & HAIKU BATTLE at The Queen Bean Coffee & Social House
  - **Date**: 2026-08-20 16:53:46
  - **User Avatar**: https://cdn-az.allevents.in/events8/banners/648e6eb0-66c2-11f0-aee9-7f38ce337ed4-rimg-w200-h200-dcbfbfd2-gmir
- **Review**: "So much fun for 5 yr old  and bouncing too, as well as petting angora goats and picking raspberries- a wonderful afternoon for all 3 of us!!"
  - **Rating**: 5/5
  - **By**: Bonnie OReilly
  - **Event**: 150 years of farming Festival at 34448 44th Ave, Paw Paw, MI, United States, Michigan 49079
  - **Date**: 2026-08-17 22:32:07
  - **Photo**: https://cdn2.allevents.in/transup/75/a7bb2d0ec84511be8a89330cd979fb/images/IMG_8389.webp
  - **User Avatar**: https://lh3.googleusercontent.com/a/ACg8ocIcSujO0ziFj7fsmZQqLpIpZuQd0nb9dpnt5iMYRTtZEBe30g=s96-c?sz=200
- **Review**: "Had a good time, lots of great items and good eats. The car show was an bonus."
  - **Rating**: 4/5
  - **By**: Caren
  - **Event**: Old School Day at the Rail Yards Market at 777 1st St SW, Albuquerque, NM, United States, New Mexico 87102
  - **Date**: 2026-08-17 14:44:22
  - **Photo**: https://cdn2.allevents.in/transup/b7/3e206151d241dc8450891b56da2f7f/images/IMG_20260816_124554184_HDR.webp
  - **User Avatar**: https://cdn-az.allevents.in/events8/banners/209d7210-86c3-11f1-a8a4-631b175f3d78-rimg-w200-h200-dc5d91d2-gmir
- **Review**: "It was a better venue than last years. It's still a small festival with potential for growth."
  - **Rating**: 4/5
  - **By**: Peter Jorge
  - **Event**: CTXMF 2026 at Sean Patrick's Irish Pub N' Texas Grub
  - **Date**: 2026-08-16 23:23:03
  - **Photo**: https://cdn2.allevents.in/transup/8f/00ea75f3744dbab30e331a555ebfd5/images/PXL_20260815_220425542.MP.webp
  - **User Avatar**: https://lh3.googleusercontent.com/a/ACg8ocLOKQOr8mk7cmXu-GAYA7t7NBXxLc9iaI3IqYGdU8dA8PUThDrP=s96-c?sz=200
- **Review**: "Two Great muscle cars I voted on and two Vert unique entries. Great car show. Just need to know what cars came in for firstvthrough 5th after votes. Had to leave before the announcement. 😢"
  - **Rating**: 5/5
  - **By**: Don Bybee
  - **Event**: Downtown McKinney Classic Car Show at 307 N Kentucky St
  - **Date**: 2026-08-16 20:53:56
  - **Photo**: https://cdn2.allevents.in/transup/79/c88f10d48a4e32bd79a1e53328a62e/images/IMG_0823.webp
  - **User Avatar**: https://cdn-az.allevents.in/events4/banners/aa5b5bb4ae4785ffd40f7f4a26fc9f1072c1911debdbd6e0c8e47dfaf9f372e1-rimg-w200-h200-gmir?v=1707687005
- **Review**: "Fun afternoon...Don't know how many times I've seen Tommy Boy, but it had been years...Enjoyed it."
  - **Rating**: 5/5
  - **By**: Fried Okra 70
  - **Event**: Movie Matinee: Tommy Boy at Gillioz Theatre
  - **Date**: 2026-08-20 15:16:49
  - **User Avatar**: https://lh3.googleusercontent.com/a/ACg8ocJCWoj4JeJ7indyRue8Q4uDQUd1bvPGZocVnE9a0EXwgIotQlmaug=s96-c?sz=200
- **Review**: "The encore band was fantastic! Great choice of music and fantastic musicians!"
  - **Rating**: 5/5
  - **By**: don lundy
  - **Event**: The Encore Band at The Sanctuary Hotel 6pm at The Sanctuary at Kiawah Island Golf Resort
  - **Date**: 2026-08-16 16:57:50
  - **Photo**: https://cdn2.allevents.in/transup/42/ec24a1e1ec4e01928dd2c31c30ebce/images/e9a80eb55b3fe6e62f27afa6eed89b2a07f6146d60eb42748e3f402537234478_exif.webp
  - **User Avatar**: https://www.gravatar.com/avatar/27161d8c8828a4b8873ff95248e84665?s=800&d=identicon&r=g
- **Review**: "back in time to a quieter time.  variety of homestead settings, hand tools, sawmill, music, hands-on"
  - **Rating**: 5/5
  - **By**: dm fl
  - **Event**: Annual Blackberry Threshing, Farm & Antique Show at 25313 US-2, Grand Rapids, MN, United States, Minnesota 55744
  - **Date**: 2026-08-16 15:47:06
  - **Photo**: https://cdn2.allevents.in/transup/80/317efec2b946e5a0474ca4688a71ec/images/0385a28f6a6f7849b572a6dc9e9c56bf6a8164a5fa98d769d096966e19f624ad_exif.webp
  - **User Avatar**: https://lh3.googleusercontent.com/a/ACg8ocJfLRCjnphNedqvgpvYoW7lM5w10w6SrS2Ps8tn0NSKOiQyFrjq_Q=s96-c?sz=200
- (more moments omitted)

## Frequently Asked Questions

- **Q**: What are the top events happening in Chestertown?
  - **A:** Here are the top events in Chestertown: 30th & Final Chestertown Jazz Festival (Sat, 12 Sep at 12:00 pm, at Wilmer Park, Chestertown), Schooner SULTANA Public Sails 2026-September (Fri, 04 Sep at 05:00 pm, at Chestertown Marina), 2026 Downrigging Tall Ship Sails: SUNDAY NOV 1, 1:00pm-3:30pm (Sun, 01 Nov at 01:00 pm, at Chestertown Marina), Grape Expectations: Brampton 1860 “Harvest Afterglow: A Late Summer Supper” (Thu, 17 Sep at 06:00 pm, at 25227 Chestertown Rd), Mooday's Music, LLC Open House (Sat, 29 Aug at 09:00 am, at 115 S Lynchburg St, Suite D, Chestertown, MD, United States, Maryland 21620).
- **Q**: How can I find events happening in Chestertown?
  - **A:** You can discover upcoming events in Chestertown on AllEvents.in. Browse by category, date, or venue to find events that match your interests.
- **Q**: How do I buy tickets for 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 event venues in Chestertown?
  - **A:** Some popular venues hosting events in Chestertown include Wilmer Park, Chestertown Marina, 25227 Chestertown Rd, 115 S Lynchburg St, Suite D, Chestertown, MD, United States, Maryland 21620, Stillpond Creek.
- **Q**: How can I get notified about new events in Chestertown?
  - **A:** Follow Chestertown on AllEvents.in to receive notifications when new events are listed in your city.

## Chestertown at a Glance

- **Total Upcoming Events**: 30
- **Featured Events**: 5
- **Followers**: 399
- **Trending Now**: This Weekend: 1, Live Music: 3

## Trending Categories in Chestertown

- [Festivals (4 events)](https://allevents.in/chestertown/festivals)
- [Live Music (3 events)](https://allevents.in/chestertown/live-music)
- [This Weekend (1 events)](https://allevents.in/chestertown/this-weekend)

## Seasonal & Special Events in Chestertown

- [Labor Day Events in Chestertown](https://allevents.in/chestertown/labor-day)
- [Best Pumpkin Patches Near Chestertown](https://allevents.in/chestertown/pumpkin-patch)

## Explore Chestertown

- [Car Shows 2026 In United States](https://allevents.in/events/car-shows-in-usa)
- [Chestertown Festival Guide 2026](https://allevents.in/chestertown/festivals)
- [Labor Day 2026 Events & Celebrations In The USA](https://allevents.in/events/labor-day-celebrations-in-usa)
- [Halloween 2026 Events & Celebrations In The USA](https://allevents.in/events/halloween-events-celebrations-in-usa)
- [Live Music Events Near Chestertown](https://allevents.in/chestertown/live-music)

## Events in Nearby Cities

- [Events in Rock Hall, Maryland, United States](https://allevents.in/rock hall)
- [Events in Sudlersville, Maryland, United States](https://allevents.in/sudlersville)
- [Events in Centreville, Maryland, United States](https://allevents.in/centreville-md)
- [Events in Galena, Maryland, United States](https://allevents.in/galena-md)
- [Events in Earleville, Maryland, United States](https://allevents.in/earleville)
- [Events in Queenstown, Maryland, United States](https://allevents.in/queenstown-md)