• 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 — […]

  • Cars on High

    Cars on High
    High St. High St., Chestertown, MD, United States

    Every third Thursday, April through October, weather permitting. Owners share classic, antique, and custom cars on the 300 Block of High Street. No registration necessary.

  • We’re Still Here: Black Countryside Communities in Kent County

    Lawrence Wetlands Preserve 301 South Mill Street, Chestertown, M, United States

    Join the Historical Society of Kent County for a presentation and community discussion led by Darius Johnson, historic preservation scholar and project director for Chesapeake Heartland. Focusing on the Black countryside communities of Butlertown, Big Woods, Still Pond, and Coleman, the program highlights personal histories and community legacies often left out of the historical record. […]

    Free
  • Jim Gent Bay to Bay Bike Ride

    Every year hundreds of bicyclists from around the region converge in Kent County for the annual Jim Gent Memorial Bay to Bay Bike Ride. This year’s event is on June 22 with the rides begining in Betterton and consisting of five routes between 26 and 102 miles in length. The flat loop routes take in […]

    $45 – $55
  • First Friday

    On the first Friday of the month, downtown shops stay open until 8 pm and galleries stage opening and special events.

  • 4th of July Fireworks

    Wilmer Park

    The 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
  • Author Event – Erika Quesenbery-Sturgill

    Emmanuel Episcopal Church Parish Hall 101 North Cross St., Chestertown, M, United States

    Join author Erika Quesenbery-Sturgill and the staff at the Kent County Historical Society and The Bookplate for an evening author event at the Emmanuel Episcopal Church to discuss her new […]

    Free
  • Cars on High

    Cars on High
    High St. High St., Chestertown, MD, United States

    Every third Thursday, April through October, weather permitting. Owners share classic, antique, and custom cars on the 300 Block of High Street. No registration necessary.

  • Crazy Days

    Downtown Chestertown’s annual sidewalk sale, Crazy Days! The bargain shopping begins on Thursday, July 24 and runs through Saturday, July 26, with many stores carrying the specials into Sunday. Shops […]