Sunday, September 27
Dorchester Center for the Arts, Cambridge

11 a.m.-6 p.m.
www.dorchesterartscenter.org

Stroll down historic High Street in Cambridge all the way down to Long Wharf and enjoy this outdoor arts and craft festival, which draws more than 6,000 people each year to Cambridge for fine art, handmade crafts, live music, and Eastern Shore cuisine. Dorchester Center for the Arts to Close High Street from Poplar Street to Long Wharf.

Choptank Heritage Skipjack Races
Saturday, September 26
Downtown Cambridge
7 a.m.-noon

www.cambridgemainstreet.com

Skipjacks from all over the Chesapeake come to the beautiful waterfront in Cambridge to participate in this annual race starting at 10 a.m. Before the race, beginning at 7 a.m., enjoy coffee, pastries, and a close-up look at these historic Chesapeake sailing vessels docked at Snapper’s Waterfront Café, 112 Commerce Street. After the race, spend the afternoon in the shops, galleries, restaurants, and museums of Historic Downtown Cambridge, right down the street from the race site.