All Upcoming events

• Fri, 21 Nov, 2025 - 08:30 PM

  The Party of the Year: GATSBY

  Chesapeake Inn Restaurant & Marina

  7+ Interested

  |

  USD 65
• Sat, 01 Nov, 2025 - 07:00 PM

  Michael Christopher Band LIVE on The Deck!

  605 Second Street, Chesapeake City, MD, United States, Maryland 21915
• Sat, 08 Nov, 2025 - 07:00 PM

  Decade80 LIVE on The Deck!

  605 Second Street, Chesapeake City, MD, United States, Maryland 21915
• Sun, 30 Nov, 2025 - 06:00 PM

  Chesapeake City Christmas Tree Lighting

  Pell Gardens Park
• Sat, 13 Dec, 2025 - 05:00 PM

  Chesapeake City Candlelight House Tour 2025

  98 Bohemia Ave, Chesapeake City, MD 21915-1264, United States
• Sat, 01 Nov, 2025 - 11:00 AM

  Chesapeake City Fall Foliage Cider & Donut Cruise

  1 Bohemia Ave, Chesapeake City, MD 21915-1259, United States
• Sat, 29 Nov, 2025 - 07:00 PM

  Olivia Reynolds Band at Chesapeake City VFW

  Chesapeake City VFW
• Sat, 06 Dec, 2025 - 05:30 PM

  Bohemia River Boaters Lighted Boat Parade

  Chesapeake City Bridge
• Fri, 07 Nov, 2025 - 07:00 PM

  The Everafter LIVE on The Deck!

  605 Second Street, Chesapeake City, MD, United States, Maryland 21915
• Fri, 28 Nov, 2025 - 06:00 PM

  Chesapeake Inn

  Chesapeake Inn & Marina
• Sun, 09 Nov, 2025 - 12:00 PM

  The Chesapeake Inn

  Chesapeake Inn Restaurant and Marina
• Fri, 19 Dec, 2025 - 07:00 PM

  Just a Bit Outside @ Chesapeake Inn

  Chesapeake Inn
• Sat, 01 Nov, 2025 - 05:30 PM

  Vintner’s Table: Wine & Soup Pairing Experience - Legacy Club Event

  237 Bohemia Manor Farm Ln
• Fri, 07 Nov, 2025 - 06:00 PM

  Chesapeake City VFW

  Chesapeake City VFW
• Sat, 06 Dec, 2025 - 07:00 AM

  The Collapse: Aftermath, a Scenario Paintball Event

  OXCC - Outdoor Xtreme Chesapeake City Paintball & Airsoft
• Sun, 09 Nov, 2025 - 02:30 PM

  Santa at Sinking Springs

  Sinking Springs Retreat Center, LLC
• Sat, 20 Dec, 2025 - 06:00 PM

  Olivia Reynolds Band at Unwined on the Water

  Unwined on the Water
• Sat, 27 Dec, 2025 - 01:30 PM

  A Journey to OZ • Dec 27 & 28

  Chesapeake Inn Restaurant & Marina
• Sat, 22 Nov, 2025 - 09:00 AM

  Chesapeake City UMC Annual Christmas Bazaar

  450 Third Street, Chesapeake City, MD, United States, Maryland 21915
• Wed, 31 Dec, 2025 - 08:00 PM

  New Years Eve Deck Party 2026 at Chesapeake Inn!

  Chesapeake Inn Restaurant & Marina
• Fri, 09 Oct, 2026 - 02:00 PM

  Endless Legends

  2941 Old Telegraph Rd, , Chesapeake City, MD, United States, Maryland 21915
• Wed, 31 Dec, 2025 - 08:00 PM

  NYE Ballroom Bash 2026 at Chesapeake Inn!

  Chesapeake Inn Restaurant & Marina
• Sun, 14 Dec, 2025 - 12:00 PM

  Holiday Sip & Shop "Between The Vines"

  237 Bohemia Manor Farm Ln
• Thu, 27 Nov, 2025 - 10:00 AM

  Thanksgiving At The Tank Room

  237 Bohemia Manor Farm Ln
• Sat, 15 Nov, 2025 - 06:00 PM

  Baker’s Restaurant Presents Max & Denise “Acoustic With An Edge”

  Baker's
• Sat, 15 Nov, 2025 - 02:00 PM

  Justin Taylor | Chesapeake City MD

  Bayard House Restaurant
• Thu, 27 Nov, 2025 - 12:00 PM

  Annual Thanksgiving Buffet 2025

  605 Second Street, Chesapeake City, MD, United States, Maryland 21915
• Sat, 30 May, 2026 - 01:00 PM

  Just a Bit Outside @ Chesapeake Imn

  Chesapeake Inn Restaurant and Marina
• Sun, 21 Dec, 2025 - 05:00 PM

  Chesapeake Inn Santa Dinner with Friends • Dec 21

  Chesapeake Inn Restaurant & Marina
• Sat, 13 Dec, 2025 - 10:00 AM

  Annual Toy Drive 2025

  Sinking Springs Retreat Center, LLC
• Sat, 14 Feb, 2026 - 06:00 PM

  Valentine's at The Chesapeake Inn

  Chesapeake Inn & Marina
• Sun, 02 Nov, 2025 - 12:00 PM

  Joyride (The duo!) @ Chesapeake Inn, Chesapeake City, MD

  Chesapeake Inn
• Sun, 02 Nov, 2025 - 02:00 PM

  UnWined on the Water

  Unwined on the Water
• Sat, 13 Dec, 2025 - 08:00 AM

  Wreaths Across America with IW Delaware!

  Delaware Veterans Memorial Cemetery
• Fri, 07 Nov, 2025 - 07:00 PM

  THE EVERAFTER @ Chesapeake Inn

  Chesapeake Inn
• Wed, 19 Nov, 2025 - 06:00 PM

  A-Nora-ble Paint Your Own Mini Part

  100 Bohemia Ave
• Sat, 06 Dec, 2025 - 10:00 AM

  Chesapeake Inn Santa Brunch with Friends • DEC 6, 13, & 20

  Chesapeake Inn Restaurant & Marina