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  • 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.

  • Chestertown Tea Party Festival

    Step back in time and celebrate Chestertown’s rich colonial history at the annual Tea Party Festival! Held Memorial Day weekend, this beloved event features historical reenactments (including the iconic tea toss into the Chester River!), live music, a colonial parade, artisan vendors, local food, family-friendly activities, and more. It’s a weekend full of charm, community, […]

  • Chestertown Memorial Day Parade

    Memorial Park 230 High Street, Chestertown, MD

    Music 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 Park

    A 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

  • First Friday

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

  • Historical Society of Kent County’s 50th House & Garden Tour: Hidden Gems of Chestertown

    Bordley History Center 301 High St., Chestertown, M, United States

    The Historical Society's 50th House & Garden Tour takes place on June 7 from 11 am to 4 pm. This year's tour showcases hidden gems in Chestertown: historic homes ranging from 18th-century residences to early 20th-century Craftsman styles, all nestled within a charming and walkable neighborhood in Chestertown's Historic District. Docents at each location will share insights […]

  • Bookplate Author Event – Chris Filstrup

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

    "The Turban: A History from East to West" by Chris Filstrup and Jane Merrill Unravel the fascinating history of the turban, from its origins to its religious uses and its appearance in contemporary fashion and culture. A turban is a strip of cloth folded and wrapped around the head; however, this description includes multifarious forms […]

    Free

  • A Night in New Orleans – part of the 2025 Delmarva Pride Festival!

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

    The Delmarva Pride Center is excited to announce its upcoming event, “A Night in New Orleans,” a vibrant fundraiser celebrating Pride Month and supporting the ongoing efforts to promote equality and inclusivity in the community. The event is scheduled for Thursday, June 12, 2025, with a VIP Cocktail Hour starting at 6:00 PM and Concert […]

  • HEROES OF THE CHESAPEAKE- JUNETEENTH CELEBRATION

    Fountain Park Chestertown, MD, United States

    Friday, 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

  • Heroes of the Chesapeake – Juneteenth Celebration

    Fountain Park Chestertown, MD, United States

    Friday, 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