ESVA ChamberFest 2026

The Eastern Shore of Virginia Chamber of Commerce is excited to announce its annual ChamberFest music and tailgating celebration Friday, May 15 and Saturday, May 16, 2026 at the scenic Cape Charles waterfront on the Chesapeake Bay. This much-anticipated spring event is part concert, part tailgate party — and all fun for music lovers, friends, and neighbors alike.

ChamberFest returns with an expanded two-day format featuring live music, food trucks, adult beverages, designated tailgating spots, and plenty of reasons to gather by the water for the best spring outing on the Shore. Tailgate guests are invited to bring a 10′ × 10′ tent, chairs, coolers, and enjoy the day with friends — secure your spot early, as these limited spaces sell out quickly! Both tailgate and individual ticket holders will have full access to the entertainment, food trucks, and beverage stations throughout the festival.

Lineup Highlights:

🎶 Saturday, May 16 begins at 3:00 PM with local favorites Fil Rhythm, bringing high-energy tunes and hometown vibes.

🎤 Following them, “The Boys in the Band” will get the crowd singing and dancing with beloved country hits from the catalog of Alabama, offering something familiar and fun for everyone — even if fans don’t recognize the tribute band’s name, they’ll know the music.

🎸 Headlining the night is the Roots & Boots show featuring Aaron Tippin and Sammy Kershaw, two iconic country artists whose music defined the 1990s country scene and continues to delight fans of all ages. Their performances include fan-favorite hits that emphasize patriotic pride, storytelling, and sing-alongs, perfectly complementing the festival’s upbeat, celebratory atmosphere.

Ticket Information:

• Early Bird Pricing: Saturday only — $45*

• Weekend Pass (Friday & Saturday): $60*

(*Additional credit card processing fees may apply when purchased online at esvachamber.org.)

Individual ticket holders are encouraged to bring a chair or blanket to relax on the lawn while enjoying the performances and waterfront views. Tailgating spots are available for those who want to make a day of it — but they’re expected to sell out, so register early!

This 21+ festival is designed to be a memorable afternoon and evening of live music, great food, and community connection. ChamberFest the perfect gateway into summer on Virginia’s Eastern Shore.

For more details and to purchase tickets, visit esvachamber.org. Additional announcements and special attractions will be shared as ChamberFest approaches — stay tuned to the ChamberFest event page on Facebook!

Plan a full weekend by staying on the Eastern Shore - find lodging options at www.visitesva.com.

About the Eastern Shore of Virginia Chamber of Commerce:

The mission of the Eastern Shore of Virginia Chamber of Commerce is to serve, promote, and connect the businesses and communities of the Eastern Shore.

Also check out other Concerts in Cape Charles, Music events in Cape Charles, Entertainment events in Cape Charles.