Upcoming Chestertown Events

Check out what's happening all around Chestertown, MD

The 30th Annual Chestertown Tea Party Distance Classic Race and Run for Radcliffe (5K & 10-Mile Run)

 Sat, 23 May at 08:00 am Wilmer Park

The Spongebob Musical

 Fri, 17 Apr at 07:00 pm Garfield Center for the Arts at the Prince Theatre USD 18 to 29

Saturday in the Park!

 Sat, 30 May at 12:00 pm Wilmer Park

GCA Presents "The Spongebob Musical" NEW DATES

 Fri, 01 May at 07:00 pm Garfield Center for the Arts at the Prince Theatre USD 18 to 29

Schooner SULTANA Public Sails 2026-May

 Sat, 02 May at 11:00 am Chestertown Marina USD 23 to 44

Sultana's Annual Gala, May 9, 2026

 Sat, 09 May at 06:00 pm Clovelly Farm USD 200

Rt 50 live at Rolph’s Wharf Sandbar!

Sun, 24 May at 02:00 pm Rolph's Wharf Sandbar

Schooner SULTANA Public Sails 2026-June

 Fri, 26 Jun at 05:00 pm Chestertown Marina USD 23 to 44

Schooner SULTANA Public Sails 2026-August

 Fri, 14 Aug at 05:00 pm Chestertown Marina USD 23 to 44

Schooner SULTANA Public Sails 2026-September

 Fri, 04 Sep at 05:00 pm Chestertown Marina USD 23 to 44

Schooner SULTANA Public Sails 2026-July

 Fri, 24 Jul at 05:00 pm Chestertown Marina USD 23 to 44

Drawing the Line: Visual Journaling — The Identity Series

 Thu, 09 Apr at 06:00 pm Artist Michael Bell Studio & Workshops USD 495

Aunt Sarah’s Playground 3rd Annual Community Easter Egg Hunt

 Sat, 04 Apr at 01:00 pm Wilmer Park, South Cross Street, Chestertown, MD, USA Free

Oysters and Indians Public Paddle - 2026 - Sultana Education Foundation

 Sat, 19 Sep at 10:00 am Stillpond Creek USD 12 to 49

WellFest at Wilmer -- A Community Wellness Event for the whole Kent County community!

 Sat, 16 May at 10:00 am Wilmer Park

Easter Elegant Afternoon Tea at Brampton 1860

 Sun, 05 Apr at 02:00 pm 25227 Chestertown Rd USD 29 to 61

Free Community Meditation

 Sat, 11 Apr at 08:00 am 932 Washington Avenue, Chestertown, MD, United States, Maryland 21620

Alcohol Ink with Tina Hanson

 Sat, 16 May at 01:00 pm 343 High St, Chestertown, MD 21620-1316, United States

Grape Expectations: Brampton 1860 “Spring Garden Party Glam”

 Thu, 23 Apr at 06:00 pm 25227 Chestertown Rd USD 98

Washington College Field Hockey Spring Prospect Day

 Sun, 12 Apr at 10:00 am Washington College USD 98

First 2026 Permaculture Potluck

 Sat, 25 Apr at 06:00 pm 508 Washington Ave Bldg# CG1, Chestertown, MD 21620

The High and Wides with Caleb Stine

 Fri, 08 May at 08:00 pm Garfield Center for the Arts at the Prince Theatre USD 29

Mother's Day Elegant Afternoon Tea at Brampton 1860

 Sun, 10 May at 02:00 pm 25227 Chestertown Rd USD 29 to 61

Mindfulness In nature

 Sat, 04 Apr at 09:30 am Lawrence Wetlands Preserve Free

Whisky Train at JelLEEfish Joel's

 Sun, 31 May at 01:00 pm Jel-leefish Joel's

Kent Ag Center Spring Auction & Family Fun Day

 Sat, 18 Apr at 09:00 am 21349 Tolchester Beach Rd, Chestertown, MD

Sundae Sunday Fundraiser

 Sun, 26 Apr at 02:00 pm Stam’s Luncheonette

Mending Workshop

 Sat, 06 Jun at 01:00 pm 343 High St, Chestertown, MD 21620-1316, United States

KCMS Title 1 Presents FAMILY Reading Paint Night & Party

 Thu, 23 Apr at 05:30 pm Kent County Middle School, East Campus Avenue, Chestertown, MD, USA Free

Experience the Bay with Chesapeake Scenes

 Fri, 15 May at 07:00 pm Lawrence Wetlands Preserve Free

Scars&Glory PartII Draw Your Weapon

Sun, 17 May at 03:30 pm 8814 Fairlee Rd, Chestertown, MD 21620-3803, United States, Fairlee, MD

Campbell and Furneisen Law Anniversary Celebration!

Fri, 03 Apr at 05:00 pm 210 S. Cross St, Chestertown, MD, United States, Maryland 21620

Bi-Monthly Bluegrass Jam

 Sat, 07 Mar at 01:00 pm Lawrence Wetlands Preserve Free

Kenah One Ribbon Cutting

 Fri, 10 Apr at 12:00 pm 512 Washington Ave Free

Community Meet & Greet

 Wed, 08 Apr at 06:00 pm 206 S Queen St, Chestertown, MD 21620-1524, United States