• 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
  • 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
  • Lunch & Lore with Erika Sturgill

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

    Please join us at noon on Thursday, May 28 for our latest Lunch & Lore, when author and Historical Society favorite Erika Sturgill will speak to us on the topic "Busy As A Mother: American Women." Bring a brown-bag lunch, your curiosity, and your questions for another engaging lunchtime discussion!

    Free