Live Music in Chesapeake City

• Sat, 21 Feb, 2026 - 07:00 PM

  Bridgerton Ball!

  Sinking Springs Retreat Center, LLC

  54+ Interested
• Fri, 20 Feb, 2026 - 07:00 PM

  Kris V and Richie D LIVE on The Deck

  605 Second Street, Chesapeake City, MD, United States, Maryland 21915

  4+ Interested
• Sat, 21 Feb, 2026 - 08:30 PM

  Dueling Pianos with The Philly Keys • February 21

  Chesapeake Inn Restaurant & Marina

  USD 28
• Fri, 20 Feb, 2026 - 08:30 PM

  Dueling Pianos with The Philly Keys • February 20

  Chesapeake Inn Restaurant & Marina

  USD 28
• Sat, 14 Feb, 2026 - 07:00 PM

  Exit 93 LIVE on The Deck

  605 Second Street, Chesapeake City, MD, United States, Maryland 21915

  12+ Interested
• Sun, 15 Mar, 2026 - 12:00 PM

  Chesapeake Inn

  Chesapeake Inn Restaurant and Marina
• Sat, 28 Feb, 2026 - 07:00 PM

  DECADE80 LIVE on The Deck

  605 Second Street, Chesapeake City, MD, United States, Maryland 21915

  52+ Interested
• Thu, 26 Mar, 2026 - 04:30 PM

  Mocks & Socks

  Sinking Springs Retreat Center, LLC

  23+ Interested
• Sun, 15 Feb, 2026 - 12:00 PM

  Vertigo Breeze Rockin the Chesapeake Inn

  Chesapeake Inn
• Sat, 21 Feb, 2026 - 07:00 PM

  The FM Band LIVE on The Deck

  605 Second Street, Chesapeake City, MD, United States, Maryland 21915

  8+ Interested
• Fri, 27 Feb, 2026 - 07:00 PM

  Just a Bit Outside LIVE on The Deck!

  605 Second Street, Chesapeake City, MD, United States, Maryland 21915

  5+ Interested
• Sat, 28 Mar, 2026 - 06:00 PM

  The Amigos at Baker's Restaurant

  Baker's

  28+ Interested