Chestertown Parties Events

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

Wilmer Park 23 May 2026

Sultana's Annual Gala, May 9, 2026

Clovelly Farm 9 May 2026

Schooner SULTANA Public Sails 2026-May

Chestertown Marina 2 May 2026

Schooner SULTANA Public Sails 2026-August

Chestertown Marina 14 Aug 2026

Schooner SULTANA Public Sails 2026-June

Chestertown Marina 26 Jun 2026

Schooner SULTANA Public Sails 2026-July

Chestertown Marina 24 Jul 2026

Grape Expectations: Brampton 1860 “A Taste of the Emerald Isle”

25227 Chestertown Rd 26 Mar 2026

Spring Fling

Garfield Center for the Arts 20 Mar 2026

Easter Elegant Afternoon Tea at Brampton 1860

25227 Chestertown Rd 5 Apr 2026

Free Concert With Pam Ortiz & Karen Sommerville

207 S Cross St, Chestertown, MD 21620-1512, United States 20 Mar 2026

Whisky Train at JelLEEfish Joel's

Jel-leefish Joel's 31 May 2026

Mother's Day Elegant Afternoon Tea at Brampton 1860

25227 Chestertown Rd 10 May 2026

Hannah Montana 20th Anniversary Music Class - Adults Only

115 S Lynchburg St, Suite D, Chestertown, MD, United States, Maryland 21620 21 Mar 2026

Kent Ag Center Spring Auction & Family Fun Day

21349 Tolchester Beach Rd, Chestertown, MD 18 Apr 2026

Sundae Sunday Fundraiser

Stam’s Luncheonette 26 Apr 2026

Campbell and Furneisen Law Anniversary Celebration!

210 S. Cross St, Chestertown, MD, United States, Maryland 21620 3 Apr 2026

Kicking off HOT AUGUST NIGHTS at FairLEE’s!!

FairLee’s Restaurant & Bar 15 Aug 2026