Upcoming Chestertown Events

Check out what's happening all around Chestertown, MD

Legacy Day 2025

 Fri, 15 Aug at 06:00 pm Chestertown, Md 21620

Chestertown Elks Dirt Sprints

 Sat, 27 Sep at 07:00 pm 8631 Bell Rose Ln, Chestertown, MD 21620-4501, United States

Ink & Indie - Book Signing Event - 2025 - Saturday | Main Signing Event

 Sat, 04 Oct at 10:00 am The Bank

Kids' Night: Game Night (Ages 5-11)

 Fri, 05 Sep at 06:00 pm 151 Dixon Drive Suite 4, Chestertown, MD, United States, Maryland 21620

Backyard Beekeeping (Third Thursday Speaker Series)

 Thu, 21 Aug at 06:00 pm 301 S Mill St, Chestertown, MD 21620, United States

🎈Cookie Chronicles Book Party 🎈

Fri, 05 Sep at 05:00 pm 112 S Cross St, Ste D, Chestertown, MD

Kids' Night: Disney Night (Ages 2-11)

 Fri, 19 Sep at 06:00 pm 151 Dixon Drive Suite 4, Chestertown, MD, United States, Maryland 21620

Chestertown Women's Circle- September

 Sun, 21 Sep at 02:00 pm 218 Round Top Rd Free

That's the Spirit

 Sat, 13 Sep at 04:30 pm Watershed Alley USD 135 to 189

Grape Expectations: A Playful Plates Party at Brampton 1860, Gourmet Picnic

 Thu, 21 Aug at 06:00 pm 25227 Chestertown Rd USD 75

300-Hour Yoga Teacher Training

 Fri, 03 Oct at 05:00 pm 932 Washington Avenue, Chestertown, MD

Kids' Nights: Craft Night (Ages 5-11)

 Fri, 10 Oct at 06:00 pm 151 Dixon Drive Suite 4, Chestertown, MD, United States, Maryland 21620

Kent AG Center Dog Days featuring Delmarva DockDogs

 Sat, 13 Sep at 07:30 am Kent County Fair / Kent Ag Center

Rt. 50 at Rolphs Wharf Marina

Sat, 23 Aug at 02:00 pm ROLPHS WHARF MARINA

Kids' Nights: Halloween Movie Night (Ages 2-11)

 Fri, 24 Oct at 06:00 pm 151 Dixon Drive Suite 4, Chestertown, MD, United States, Maryland 21620

Left Of The Dial - Live! From Jel-LEE-fish Joel's!!! Chestertown, MD

 Sat, 06 Sep at 02:00 pm Jel-leefish Joel's

Aglow Meeting...Please join us!!

 Sun, 17 Aug at 03:00 pm Women in Need, Inc Chestertown, MD 21620

Brampton 1860 Fall Open House

 Sun, 07 Sep at 12:00 pm 25227 Chestertown Rd Free

2025 Chestertown Jazz Festival

 Sat, 06 Sep at 12:00 pm Wilmer Park USD 45

Sultana's Downrigging-Festival Village Passes-2025

 Fri, 31 Oct at 03:00 pm Chestertown Marina USD 28 to 55

Elementary Homeschool Music Movie Day @ Flagship Premiere Cinemas

 Fri, 26 Sep at 10:00 am 21 Washington Sq, Chestertown, MD 21620-1041, United States

Tolchester Shanty Bar

 Sat, 06 Sep at 06:00 pm Tolchester Marina

Shelter Expansion Rally

 Sun, 05 Oct at 03:00 pm Presbyterian Church of Chestertown 905 Gateway Dr, Chestertown, MD

Vice Squad's Labor Day Weekend Jam at the Sandbar

 Sat, 30 Aug at 03:00 pm ROLPHS WHARF MARINA

"Rhythm-N-Vines"

 Sat, 06 Sep at 01:00 pm 9155 American Legion Rd USD 29 to 55

Downrigging Weekend Sails--Friday, October 31, 2:30pm-5:00pm

 Fri, 31 Oct at 02:30 pm Chestertown Marina USD 49 to 71

Suffering and the Sovereignty of God

 Fri, 07 Nov at 07:00 pm 400 Morgnec Rd, Chestertown, MD 21620-1021, United States

Back to School Health Fair/Feria de salud para el regreso a clases

 Thu, 21 Aug at 03:00 pm 126 Philosophers Ter, Chestertown, MD 21620-1715, United States

Kent Goes Purple 5K Color Fun Run/Walk

 Sun, 07 Sep at 08:30 am Wilmer Park

Back-2-School Open House

 Mon, 08 Sep at 05:00 pm 903 Washington Ave., Suite # 3, Chestertown, MD, United States, Maryland 21620

Downrigging Weekend Sails--Saturday Morning, Nov. 1, 10:30am-1:00pm

 Sat, 01 Nov at 10:30 am Chestertown Marina USD 44 to 71

Downrigging Weekend Sails--Saturday Afternoon, Nov. 1, 2:30pm-5:00pm

 Sat, 01 Nov at 02:30 pm Chestertown Marina USD 40 to 71

Chesapeake Bound - Book Signing @The Bookplate, Chestertown, MD

 Sat, 01 Nov at 03:00 pm The Bookplate

Downrigging Weekend Sails--Sunday, Nov. 2, 1:00pm-3:30pm

 Sun, 02 Nov at 01:00 pm Chestertown Marina USD 44 to 71

Eastern Neck Wildlife Refuge: Can it Survive Funding Cuts?

 Mon, 18 Aug at 05:00 pm Unitarian Universalists of the Chester River

Waterfowl and Foliage Public Paddle - 2025- Sultana Education Foundation

 Sun, 26 Oct at 10:00 am Rileys Mill Landing USD 12 to 49

Ink & Indie 2025 - Book Signing Event!

Fri, 03 Oct at 06:00 pm The Bank

Tolchester Marina The Shanty Beach Bar

 Sat, 06 Sep at 05:00 pm The Shanty Beach Bar at Tolchester Marina

Annual Meeting

 Tue, 21 Oct at 04:00 pm 343 High St, Chestertown, MD 21620-1316, United States

Region 6: Wilmer Park Meet-Up

 Wed, 08 Oct at 01:00 pm 413 S Cross St, Chestertown, MD 21620-4768, United States

Chestertown Challenge

 Sun, 12 Oct at 09:00 am Wilmer Park

Schooner SULTANA Public Sails 2025-September

 Sat, 13 Sep at 11:00 am Chestertown Marina USD 23 to 44