Festivals in Chestertown

Check out happening festivals events 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

Saturday in the Park!

 Sat, 30 May at 12:00 pm Wilmer Park

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

2026 Chestertown Pride Festival - All Ages Dance Party!

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

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

Memorial Day Jam at the Sandbar

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