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June 2025
Family Arts & Barks Festival
No one wants to leave their furry friend behind on a beautiful summer day and the Family Arts & Barks Festival at The Bay School is the perfect opportunity to join in the fun with EVERYONE—two- AND four-legged, with AND without fur! Join us for a fun-filled day of family-friendly activities at The Bay School and bring your dog along! There will be a variety of activities to involve the whole family, including your dog: Feeling artsy? These are just…
Find out more »Gwynn’s Island Festival
The Gwynn's Island Festival has a variety of handmade crafts and local vendors, including jewelry, leather, paintings and photography. The festival will also feature live music, Lord Dunmore skits, food vendors, and a kids zone!
Find out more »July 2025
Faerie Tea
Bring Your Own Teacup • Faerie Dress Encouraged, Tea & Faerie-Inspired Tasties • Games & Activities • Door Prizes • Learn Fae & Tea Lore • Silent Auction • Vendors • Make a necklace with Virginia Coyle • Faerie Shopping Boutique • Raffles Sign up for Faerie Hair for an additional $20, by appointment only.
Find out more »Party at the Wharf 2025 Concert Series
Stay tuned for a listing of performers and food trucks! All concerts are family-friendly! All cost $5, except 5/17 Party, which is free as part of the Tour de Chesapeake.
Find out more »September 2025
Mathews Market Days 2025
Mathews Market Days is an annual festival held the first Friday and Saturday after Labor Day. We invite locals, visitors, guests, family, and friends to join us as we share the showcase of a creative community. Arts & crafts, food, and informational vendors will be in attendance alongside live music each day, a children’s area and an annual car show on Saturday. Grab some dinner from our food vendors and enjoy Saturday night’s street dance. We hope to see you…
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