Events

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  • 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 […]

  • First Friday

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

  • Reimagined Runway

    Garfield Center for the Arts 210 High Street, Chestertown, MD, United States

    This year’s event will be held on Saturday, August 2, 2025 at the Garfield Center for the Arts and promises a fresh twist on our beloved show, blending high-style fashion […]

    $50 – $250

  • Kent County: Recovered Histories

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

    Join Dr. Lucy Maddox, Professor Emeritus of History and American Studies at Georgetown University and the 2024–25 Patrick Henry History Fellow at the Starr Center for the Study of the […]

  • Crabs on High

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

    Sink your claws into summer fun at Echo Hill Outdoor School's 2nd Annual Crab Feast! Join us on Saturday, August 2, 2025, from 5:30-8pm at the foot of High Street […]

    $85