• 4th of July Fireworks

    Wilmer Park

    The Town of Chestertown hosts their annual fireworks display on Friday, July 4th. The display will begin at dark, around 9:10 pm. Viewing area will be at Wilmer Park, 413 Cross Street, Chestertown. In case of brief rain, the fireworks will be set off when the rain stops. Rain date: July 5, 2025

    Free
  • Reimagined Runway

    Garfield Center for the Arts 210 High Street, Chestertown, MD, United States

    This year’s event will be held on Saturday, August 2, 2025 at the Garfield Center for the Arts and promises a fresh twist on our beloved show, blending high-style fashion with artistic flair in a dynamic, immersive experience. Enjoy our stunning runway presentation, live entertainment, and delicious food — all while supporting RiverArts’ mission. Don’t […]

    $50 – $250
  • Crabs on High

    High St. High St., Chestertown, MD, United States

    Sink your claws into summer fun at Echo Hill Outdoor School's 2nd Annual Crab Feast! Join us on Saturday, August 2, 2025, from 5:30-8pm at the foot of High Street for all you can eat crabs, shrimp, and fried chicken set against the scenic backdrop of the Chester River. Don't miss this chance to savor […]

    $85
  • FurEver Family Fest – Let’s Clear the Shelter!

    Animal Care Shelter for Kent County 10168 Worton Road, Chestertown, MD

    This is a Family Fun event with food vendors, face painting, demonstrations. Come and consider adopting one of our very special pets just waiting for the FURever home. Raffles & Prizes and Fun for the whole family!

    Free
  • Birds & Brunch

    SG Hall: 485 S. Cross St., Chestertown, MD 21620 485 S. Cross St, Chestertown, United States

    A free public event hosted by the town of Chestertown and the Center for Environment & Society. Join us for a morning of: Coffee & light breakfast Guided bird walks […]

    Free
  • RiverArts Annual Holiday Show & Sale

    RiverArts 343 and 200B High Street, Chestertown, United States

    November 14- December 22, 2025 Locations: RiverArts Gallery, 343 High Street Store at RiverArts, 200B High Street Hours: Wednesday–Friday | 11 AM–4 PM Saturday | 9 AM–4 PM Opening Receptions (both locations): Friday, Nov 14 | 5:00 –7:00 pm Dickens of a Christmas First Friday (both locations): Friday, Dec 5 | 5:00 –7:00 pm Celebrate […]

  • WC-ALL Spring Semester Registration

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

    It's time to explore, connect and learn! Join us for a semester of discovery with interesting and thought-provoking courses—some brand new, others beloved favorites—all taught by knowledgeable and passionate instructors. Keep learning. Keep growing. Join WC-ALL this spring!

    Free
  • 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
  • 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 […]