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

2026 Chestertown Pride Festival!

 Sat, 02 May at 01:00 pm 413 S Cross Street, 21620

Schooner SULTANA Public Sails 2026-May

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

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

LHM debuts @ The Shanty Beach Bar at Tolchester Marina! (Chestertown, MD)

 Sat, 30 May at 07:00 pm The Shanty Beach Bar at Tolchester Marina

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

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-July

 Fri, 24 Jul 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

Loveboat Yacht Rock at the Shanty Bar at Tolchester Marina

 Fri, 04 Sep at 01:00 pm The Shanty Beach Bar at Tolchester Marina

Kent County Pedals & Picnic

 Sun, 24 May at 11:00 am Chestertown, Maryland

Drawing the Line: Visual Journaling — The Identity Series

 Thu, 07 May at 06:00 pm Artist Michael Bell Studio & Workshops USD 495

Movie & Arts Night: Drop-Off Studio Experience for Kids in Chestertown

 Fri, 15 May at 06:00 pm Artist Michael Bell Studio & Workshops USD 60

Grape Expectations: Brampton 1860 “Mexico Reimagined”

 Thu, 28 May at 06:00 pm 25227 Chestertown Rd USD 98

JJBB at the Shanty Beach Bar at Tolchester Marina

 Fri, 15 May at 07:00 pm The Shanty Beach Bar at Tolchester Marina

Saints, Sinners & Surface — A 5-Hour Abstract Collaboration Art Experience

 Sat, 16 May at 12:00 pm Artist Michael Bell Studio & Workshops USD 395

Oysters and Indians Public Paddle - 2026 - Sultana Education Foundation

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

2026 Chestertown Pride Festival - All Ages Dance Party!

 Fri, 01 May at 05:00 pm 413 S Cross Street, 21620

🦞 Cousins Maine Lobster at Tractor Supply Co. 🔥

 Wed, 29 Apr at 11:00 am 711 Washington Ave, Chestertown, MD 21620, USA

Saturday In The Park - Demos and Class

 Sat, 30 May at 12:00 pm 903 Washington Ave., Suite # 3, Chestertown, MD, United States, Maryland 21620

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

 Sat, 16 May at 10:00 am Wilmer Park

Alcohol Ink with Tina Hanson

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

Spongebob Squarepants the Musical - Chestertown

 Sat, 25 Apr at 11:00 pm Garfield Center for the Arts at the Prince Theatre

Mother's Day Elegant Afternoon Tea at Brampton 1860

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

Waterfowl and Foliage Public Paddle - 2026- Sultana Education Foundation

 Sun, 25 Oct at 10:00 am Rileys Mill Landing USD 12 to 49

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

Memorial Day Jam at the Sandbar

 Mon, 25 May at 03:00 pm ROLPHS WHARF MARINA

Whisky Train at JelLEEfish Joel's

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

Sam Shoge for Kent County Campaign Launch Event

 Wed, 06 May at 05:30 pm The Bank

Ink & Indie 2026 - Author Signing Event

Fri, 02 Oct at 06:00 pm The Bank

Tolchester Shanty Beach Bar

 Fri, 14 Aug at 06:00 pm The Shanty Beach Bar at Tolchester Marina

Elegant Afternoon Tea at Brampton 1860

 Sun, 28 Jan at 02:00 pm 25227 Chestertown Rd USD 30 to 57

Experience the Bay with Chesapeake Scenes

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

Mending Workshop

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

Summer Launch Party

 Sat, 30 May at 12:00 pm 302 Park Row, Chestertown, MD 21620-1544, United States

Scars&Glory PartII Draw Your Weapon

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

The Blueprint to Homeownership

 Sat, 06 Jun at 11:00 am 201 S Cross St Free

Picture Day Chestertown

 Sat, 16 May at 09:00 am 903 Washington Ave., Suite # 3, Chestertown, MD, United States, Maryland 21620

17 Year Anniversary Open House

 Mon, 04 May at 05:00 pm 903 Washington Ave., Suite # 3, Chestertown, MD, United States, Maryland 21620

Bi-Monthly Bluegrass Jam

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

Ink & Indie 2026 - Author Signing Event

 Sat, 03 Oct at 10:00 am 211 High St USD 61