Downtown will host an action packed September weekend coming up on September 21st and 22nd! It includes the Choptank River Skipjack Race, GrooveFEST downtown music festival, and the Dorchester Showcase. Sunday will also include a celebration of Dorchester County’s 350th Anniversary!

Join us on Saturday morning for the annual Choptank River Skipjack Race beginning approx 9am. The best place to view the race is from Long Wharf and the floating dock at the Cambridge Municipal Yacht Basin. The race will see 10 – 12 historic Skipjacks race for the Winner’s Cup. Skipjacks were historically built to dredge for Oysters and numbered in the thousands across Maryland Virginia and beyond. Now there are only about a dozen remaining. Many skipjacks were built here in Dorchester County. To learn more about the race visit the event website here.

On Saturday afternoon skip on down to the corner of Race and Cedar Street for the annual Groovefest: Downtown Music festival hosted by Cambridge Main Street. The line up include performers from across the mid-Atlantic region including Hoppie Vaughan and the Ministers of Soul hailing from Roanoke VA, UpHill Carolina Swampland Blues group from Elizabeth City, SoulTET from Baltimore MD, The Evolution Band from Cambridge MD. We will also host the CSD Jazz Band!

We’ll host food and community vendors and the adult beverages.  Bring a lawn chair or blanket and enjoy this fun family friendly event! To learn more about the festival visit the event page here!

On Sunday, September 22nd High Street plays host to the 43rd annual Dorchester Showcase, a fun family friendly arts and cultural festival organized by Dorchester Center for the Arts. The event will begin at noon and end at 5pm. For more information visit the DCA event website here. 

Sunday afternoon will also include a special celebration of Dorchester County’s 350th Anniversary hosted at the Dorchester Showcase. Dorchester County, Maryland, will celebrate its 350th Anniversary on Sept. 22 from 12 to 5pm with a multi-event tribute that features a “heritage village” with displays, historians, demonstrations, and reenactments highlighting Dorchester heritage and history, and the opening of a 50-year-old time capsule sealed in 1969. This commemoration will feature many aspects of Dorchester’s unique history and culture. Re-enactors include Daniel Firehawk Abbot with Native American culture, Millicent Sparks as Harriet Tubman, and Mary Handley as Annie Oakley, as well as Mark Durben doing an interpretation of the War of 1812.