Crazy Days
Hosted by the Downtown Chestertown Association, Crazy Days is Chestertown’s annual sidewalk sale with businesses offering crazy deals and restaurants offering crazy specials.
9 events found.
Annual Event
Featured
Downrigging Weekend
The Sultana Education Foundation's Downrigging Weekend highlights Tall Ships and Bluegrass, along with nautical history and Chesapeake Bay ecology.
Featured
Hometown Holiday
Kick off the Holiday Season with one of Downtown Chestertowns most iconic events, the arrival of Santa and Mrs. Clause on a fire truck! Enjoy the festive holiday music, candy, and some of the most iconic characters of the holiday season enjoying the downtown.
Featured
Dickens of a Christmas
Chestertown Memorial Day Parade
Memorial Park 230 High Street, Chestertown, MDMusic in Memorial Park 9:30-10:00am Parade down High Street 10:00am Remembrance and Honor Ceremony following Parade at Stage in Memorial Park
Saturday In The Park
Wilmer ParkA Community Festival of Music, Arts, Games, Pet Adoption, Health, Fitness, Food and Fun for everyone. - 10am Guided kayak tour of Radcliffe Creek - 11-4 Activities * Volleyball. Zumba, Bocce, Yoga, Chess, Cornhole, Kayaking, and more * Kayak, Canoe, SUP. Sell/Buy/Swap * Health Expo - Several health orgs will help us learn to become […]
No charge to attend or participate
National Music Festival
The National Music Festival transforms Kent County into a hub of music. Now in its 13th season, the nationally recognized event will feature music to suit virtually every taste — from symphonies and chamber music to hints of jazz. More than 30 concerts and over 200 open rehearsals are scheduled throughout the Festival in venues […]
HEROES OF THE CHESAPEAKE- JUNETEENTH CELEBRATION
Fountain Park Chestertown, MD, United StatesFriday, June 13th, 2025 the Bayside H.O.Y.A.S., will host their annual “Heroes of the Chesapeake” Juneteenth celebration at Fountain Park in Chestertown, Md. The “Heroes of the Chesapeake” Juneteenth celebration will illuminate the role of African Americans in the history of the Eastern Shore and their contributions and serves to be an exciting celebration and […]
Free
4th of July Fireworks
Wilmer ParkThe Town of Chestertown hosts their annual fireworks display on Friday, July 4th. The display will begin at dark, around 9:10 pm. Viewing area will be at Wilmer Park, 413 Cross Street, Chestertown. In case of brief rain, the fireworks will be set off when the rain stops. Rain date: July 5, 2025
Free