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  • Celebrating the Legacy of Kenneth Walley

    Kent County Public Library - Chestertown Branch 408 High Street, Chestertown, M, United States

    In 1957, Kenneth Walley opened the Walley Funeral Home on Calvert Street in Chestertown, achieving his high school ambition of becoming a mortician. As the first Black mortician and embalmer […]

  • SFW Residency: HISTORY Exhibition Opening

    Raimond Cultural Center 101 Spring Avenue, Chestertown, United States

    Opening Reception for HISTORY: An Exhibit of the SFW Resident Artist Program at the Kent Cultural Alliance. Visiting Artists Bennett Cafarelli, Mecca Lewis, and Jonna McKone share new work created […]

    Free

  • Indie Bookstore Day at The Bookplate

    The Bookplate 112 S Cross Street, Chestertown, M, United States

    Join us at the store to celebrate Independent Bookstore Day! We will have bookmark-making, games, and a very special raffle prize--win a sleepover at the store!

    Free

  • Paint The Town Show + Sale

    Chestertown RiverArts 343 High Street, Chestertown, MD, United States

    🎨✨ Paint the Town: Art Show & Sale ✨🎨 Get ready to celebrate creativity at Paint the Town, our exciting art show and sale featuring local artists! Discover vibrant paintings, […]

    Free

  • Resume Basics: What You Need To Know

    Washington College 300 Washington Ave, Chestertown, MD, United States

    Looking to strengthen your resume and stand out in today’s job market? Join us for our upcoming workshop, Resume Basics: What You Need to Know, on Thursday, April 30th at […]

    Free

  • Chestertown Garden Club’s May Mart Plant Sale

    Memorial Park 230 High Street, Chestertown, MD

    Gardeners, get ready for the annual May Mart garden sale in downtown Memorial Park Plaza. Hosted by the Chestertown Garden Club, this popular spring event features a wide array of noninvasive perennials and shrubs, as well as natives, annuals, houseplants, herbs and vegetables, all priced to sell quickly. The event will be held rain or […]

  • Eastern Shore-An Alternative View Opening Reception

    Chestertown RiverArts 343 High Street, Chestertown, MD, United States

    Opening Reception: Eastern Shore Alternative View Exhibition Be among the first to experience a bold new perspective at the opening reception of the Eastern Shore Alternative View Exhibition, hosted by Chestertown RiverArts. Join us on May 1st from 5–7 PM for an evening of creativity, conversation, and community. Meet the artists, explore thought-provoking and unconventional […]

    Free

  • First Friday

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

  • WellFest at Wilmer — May 16, 2026 — Community Wellness Festival at Wilmer Park

    WellFest at Wilmer — May 16, 2026 — Community Wellness Festival at Wilmer Park
    Wilmer Park

    Get ready for the biggest health event on the Eastern Shore—WellFest at Wilmer! Formerly known as the Health Expo and hosted by HomePorts, this year’s festival is set for May 16, 2026, 10am-2pm at Wilmer Park in Chestertown —and you won’t want to miss it! What makes WellFest at Wilmer special? This year’s expanded event […]

    Free

  • Clay Studio Fundraiser

    Chestertown RiverArts 343 High Street, Chestertown, MD, United States

    Join us for a Clay Studio Fundraiser on May 16th & 17th from 10 AM to 6 PM! Support local artists and our creative community while exploring a wide selection of beautiful, handcrafted ceramics. From functional pieces to unique works of art, there’s something for everyone to enjoy. Come out, connect with fellow art lovers, […]

    Free