Street Party Brings Blue Grass, BBQ, and More to Downtown Chestertown


Main Street Chestertown will host a Bluegrass party in the 200 block of High Street on Saturday, April 20, from noon to 3:00 p.m.  The Dirty Grass Players will provide the live music for the afternoon event, which also will offer BBQ from Phat Daddy, plus Orchard Point oysters, Lockbriar Farms ice cream, beer and wine.  In case of inclement weather, the music and fun will move up the street to Bad Alfred’s Distillery, 323 High Street. The music is free and open to the public.

The Dirty Grass Players have earned an enthusiastic following at festivals and gigs up and down the East Coast with their 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. Their music 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.

That Saturday morning starting at 9 a.m. the Chestertown Environmental Committee will host displays and family entertainment along Memorial Plaza.  And at 11 a.m., in Fountain Park, everyone is invited to join the annual count-down as the Town restarts the flow of the Hebe fountain for the season.

Weather updates will be posted on the Main Street Chestertown Facebook page. Part of a national network created by the National Trust for Historic Preservation, the nonprofit Main Street Chestertown organization works to foster an inviting, diverse and prosperous downtown. To learn more or to volunteer, contact Kay MacIntosh at 410-778-2991,

Write a Letter to the Editor on this Article

We encourage readers to offer their point of view on this article by submitting the following form. Editing is sometimes necessary and is done at the discretion of the editorial staff.


We're glad you're enjoying The Chestertown Spy.

Sign up for the the free email blast to see what's new in the Spy. It's delivered right to your inbox at 3PM sharp.

Sign up here.