Chesapeake Winter Bluegrass FESTIVAL
Schedule
Fri, 30 Jan, 2026 at 12:00 pm to Sun, 01 Feb, 2026 at 08:00 pm
UTC-05:00Location
Crowne Plaza Annapolis | Annapolis, MD
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🪕❄️ Chesapeake Winter Bluegrass Festival 2026! 🎻😀This is Annapolis’ ONLY festival 100% dedicated to bluegrass… and it’s back for Year 2!
🔥 On Stage This Year:
🎶 Lonesome River Band – award-winning headliners
🎶 Danny Paisley & the Southern Grass – IBMA Male Vocalist of the Year
🎶 Mason Via – songwriter, formerly of Old Crow Medicine Show
🎶 Valerie Smith – powerhouse vocals & originals
🎶 The Plate Scrapers - original and creative Appalachian musicianship
🎶 Geraldine – Baltimore’s old-time dance band
🎶 Black-Eyed Suzies – Maryland’s favorite female bluegrassers
🎶 Eddie Lightner & the Potomac Pickers – rising favorites
PLUS ➡️ youth “Rising Pickers” academy, jam sessions, and workshops for all levels.
📅 Jan 30 – Feb 1, 2026
📍 Annapolis, MD
👉 Tickets + info:
www.winterbluegrass.com
🎶 Don’t just hear bluegrass—live it this winter! ❄️🪕
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Where is it happening?
Crowne Plaza Annapolis, 173 Jennifer Road,Parole, Maryland, Annapolis, United StatesEvent Location & Nearby Stays:
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