• 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 5:30 PM. This session will cover the fundamentals of building a clear, focused resume that can successfully navigate applicant tracking systems and AI screening tools, […]

    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 […]

  • 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

    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
  • Slack Tide Yoga Open House

    Slack Tide Yoga 400 S. Cross St, Suite 4, Chestertown, MD, United States

    Celebrate a new chapter with us! Join Slack Tide Yoga for a free Open House as we welcome our relocation to downtown Chestertown and open the doors to our new home at 400 S. Cross St, Suite 4. Stop by Friday 6/5 from 5–7pm to tour the space, meet our team, connect with community, and […]

    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.

  • First Friday

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