Blue Grass, BBQ, and More at Downtown Chestertown Block Party


Main Street Chestertown and the Downtown Chestertown Association (DCA) will host a Fall Harvest Block Party on Saturday, September 15, from noon to 4 p.m. in the 100 block of S. Cross Street.  The Baltimore-based bluegrass band Dirty Grass Players and Chestertown’s own Jigs & Reels will provide the live music for the afternoon event, which will offer plenty of food and beverage, family activities and shopping.

Event committee chair Sean Downey, owner of Barn Life Primitives and Architectural, says the  block of Cross Street between High and Cannon Streets will fill with vendors offering pit beef barbecue, hotdogs, oysters, shaved ice, ice cream, popcorn, kettle corn, sodas, beer and wine. Entertainment will include a children’s art activity hosted by Kaleidoscope Children’s Art Studio, Corn Hole Toss, Giant Connect Four, and an Irish dance performance.

The Dirty Grass Players put an improvisational spin on traditional bluegrass vocal harmonies. Band members are Alex Berman on banjo and vocals, Ben Kolakowski on guitar and vocals, Alex Tocco on fiddle and vocals, Ryan Rogers on mandolin, and Colin Rappa on bass fiddle.  Their sound is influenced by well-known traditional bluegrass players such as Flatt and Scruggs, and “newgrass” talents that include Tony Rice and the Infamous String Dusters.   It also veers into jazz-style improvisation and rock/R&B tributes to the Grateful Dead, James Brown and other music legends.

Keeping the party going between bluegrass sets will be Paul McDonald and John Gillespie of Jigs & Reels. The duo plays Irish dance music, along with some Scottish tunes, on the fiddle, concertina and penny whistle. Their music will accompany a dance demonstration by students from the Hester Academy of Irish Dance.

Main Street Chestertown and DCA invite everyone to come downtown for the Farmers Market (bring a cooler for your produce!) and then stay downtown to enjoy some great music, food, and fun.  For more information, contact Sean Downey ( or Kay MacIntosh (, or visit the Main Street Chestertown Facebook page and click on Events.

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