• Paint The Town

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

    Each April, RiverArts brings dozens of painters to Chestertown for a four-day plein-air celebration of the Eastern Shore. Artists capture scenes throughout Kent County, with fresh works displayed and judged in our Wet Paint Show & Sale. The event culminates on Sunday with an exciting three-hour Quick Draw competition for top prizes. Come watch the […]

    Free
  • 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 […]

  • 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
  • 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 […]

    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

    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
  • First Friday

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

  • First Friday

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

  • First Friday

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