• 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
  • “Wayfaring” by Sine Nomine

    Presbyterian Church of Chestertown 905 Gateway Drive, Chestertown, MD, United States

    On Sat., May 30, Sine Nomine will return to Chestertown for "Wayfaring", a choral journey shaped by memory and the enduring search for home with works by Holst, Tuan Ward, Vaughan Williams, Thomson, McGlynn, Jacob, Paulus, Wiseman, Burton, Derrick, as well as traditional folk melodies arranged by Parker, Kirchner, and The Wallin' Jennies. The concert […]

    Free
  • Unearth My Secret! Adults-Only Summer Reading Kickoff

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

    What unusual, amazing, or humorous secret does your neighbor have? You might find out at this fast-paced, laugh-filled event! Inspired by the 1952-1967 television game show I've Got a Secret, we've recruited local celebrity panelists Jim Landskroener, Hester Sachse, and Laurie Walters to interview our contestants and try to tease out what secret they're carrying. […]