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

2026 Chestertown Pride Festival!

 413 S Cross Street, 21620 2 May 2026
FESTIVALS

Schooner SULTANA Public Sails 2026-May

 Chestertown Marina 2 May 2026
FESTIVALS USD 23 TO 44

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-August

 Chestertown Marina 14 Aug 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-September

 Chestertown Marina 4 Sep 2026
FESTIVALS USD 23 TO 44

2026 Chestertown Pride Festival - All Ages Dance Party!

 413 S Cross Street, 21620 1 May 2026
PARTIES

Saturday In The Park - Demos and Class

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

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

 Wilmer Park 16 May 2026
HEALTH-WELLNESS

Memorial Day Jam at the Sandbar

 ROLPHS WHARF MARINA 25 May 2026
MUSIC