Debut Chesapeake Winter Bluegrass festival a success

Danny Paisley enjoys the banjo of Braden DeGarmo at Winter Bluegrass – photo © Tina Heil


Last weekend bluegrass entrepreneur Danny Stewart held the debut edition of his Chesapeake Winter Bluegrass festival in Annapolis, MD. He reports that it was a tremendous success, with the host hotel, Crowne Plaza Annapolis, fully sold out and an overflow site needed to handle the turnout.

This is Danny Stewart the younger of whom we are speaking, he of US Navy Band Country Current where he plays bass, and proprietor of Turtle Hill Banjo Company, and not his father, also named Danny Stewart, who manages the annual Danny Stewart Bluegrass Cruise.

Chesapeake Winter Bluegrass was created to fill the void left behind when the COVID shutdowns saw the end of a number of indoor winter bluegrass events that had once been held in the region. Stewart was sure that people would come out for a chance to jam, attend workshops, and hear top bluegrass acts on stage during the cold weather doldrums.

And it seems he was right. Danny had multiple stages and four workshop sites going on at the same time, plus plenty of room for jamming, and lots of fans and pickers took advantage of the opportunity. Music was provided by Lonesome River Band, Mason Via, Geraldine, the Black Eyed Susies, The Plate Scrapers, and Ed Lightner, plus artist-at-large Jim Pankey who performed with a number of bands, and offered banjo workshops.

Stewart shared a number of photos from Chesapeake Winter Bluegrass 2026, and invites everyone to plan on joining them next year, January 29-31, again at the Crowne Plaza Annapolis, with early bird pricing now available.

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About the Author

John Lawless

John had served as primary author and editor for The Bluegrass Blog from its launch in 2004 until being folded into Bluegrass Today in September of 2011. He continues in that capacity here, managing a strong team of columnists and correspondents.