Celebrate the spirit of the Eastern Shore at the 2026 Chamberfest Weekend, a premier community event hosted in the heart of Cape Charles, Virginia. From May 15 to 17, 2026, the historic waterfront on Mason Avenue transforms into a vibrant festival grounds featuring live music, food and beverage trucks, and local artisans.
The weekend kicks off Friday evening at 4:00 p.m. with island vibes from the Irie Tree Band. Saturday’s high-energy lineup begins at 2:30 p.m. with performances by Fil Rhythm and Boys in the Band, a spectacular parachute jump by the All Veterans Group, and a headlining "Roots & Boots" show featuring country legends Sammy Kershaw and Aaron Tippin. This 21+ rain-or-shine event offers the perfect blend of small-town charm and big-stage entertainment. For guests staying at Sun Outdoors Cape Charles, a complimentary shuttle service is provided for stress-free transport to the waterfront.
For official ticket info and a full vendor list, visit the Eastern Shore of Virginia Chamber of Commerce here.
To experience the Eastern Shore’s stunning coastline from the water with a private luxury cruise, book your next charter with SeaEO Luxury Boat Charters for an elite getaway.