Chestertown Festivals Events

Festivals Happening Next in Chestertown, MD

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

 Wilmer Park 23 May 2026
SPORTS

Schooner SULTANA Public Sails 2026-May

 Chestertown Marina 2 May 2026
FESTIVALS USD 23 TO 44

The United States Navy Band Country Current at Chestertown Tea Party Festival

 High Street Chestertown, Md. 21620 23 May 2026
ENTERTAINMENT

Saturday in the Park!

 Wilmer Park 30 May 2026
KIDS

Schooner SULTANA Public Sails 2026-June

 Chestertown Marina 26 Jun 2026
FESTIVALS USD 23 TO 44

Schooner SULTANA Public Sails 2026-July

 Chestertown Marina 24 Jul 2026
FESTIVALS USD 23 TO 44

Schooner SULTANA Public Sails 2026-August

 Chestertown Marina 14 Aug 2026
FESTIVALS USD 23 TO 44

Schooner SULTANA Public Sails 2026-September

 Chestertown Marina 4 Sep 2026
FESTIVALS USD 23 TO 44

Saturday In The Park - Demos and Class

 903 Washington Ave., Suite # 3, Chestertown, MD, United States, Maryland 21620 30 May 2026
PERFORMANCES

Memorial Day Jam at the Sandbar

 ROLPHS WHARF MARINA 25 May 2026
MUSIC