Upcoming Chesapeake City Events

Check out what's happening all around Chesapeake City, MD

New Years Eve Deck Party 2026 at Chesapeake Inn!

 Wed, 31 Dec at 08:00 pm Chesapeake Inn Restaurant & Marina USD 39

NYE Ballroom Bash 2026 at Chesapeake Inn!

 Wed, 31 Dec at 08:00 pm Chesapeake Inn Restaurant & Marina USD 154

Dueling Pianos with The Philly Keys

 Sat, 17 Jan at 08:30 pm Chesapeake Inn Restaurant & Marina USD 28 to 39

Chesapeake Inn Santa Dinner with Friends • Dec 21

 Sun, 21 Dec at 05:00 pm Chesapeake Inn Restaurant & Marina USD 28 to 54

Dueling Pianos with The Philly Keys

 Fri, 16 Jan at 08:30 pm Chesapeake Inn Restaurant & Marina USD 28 to 39

Olivia Reynolds Band at Unwined on the Water

Sat, 20 Dec at 06:00 pm Unwined on the Water

Olivia Reynolds Band at Chesapeake City VFW

 Fri, 23 Jan at 07:00 pm Chesapeake City VFW

THE EVERAFTER @ Chesapeake Inn

 Fri, 16 Jan at 07:00 pm Chesapeake Inn

2026 NEW YEARS CELEBRATION

 Wed, 31 Dec at 08:00 pm RummuR Lounge, Bohemia Avenue, Chesapeake City, MD, USA USD 103

Boy Band Brunch with The Boy Band Project

 Sun, 25 Jan at 11:00 am Chesapeake Inn Restaurant & Marina USD 70

Cremation Seminar

 Thu, 18 Dec at 01:00 pm Baker's

12 Rooms of Christmas at the Manor; A Walking Advent Calendar Experience

 Sat, 20 Dec at 05:00 pm 237 Bohemia Manor Farm Ln USD 71

A Journey to OZ • Dec 27 & 28

 Sat, 27 Dec at 01:30 pm Chesapeake Inn Restaurant & Marina USD 32 to 53

Valentine's at The Chesapeake Inn

 Sat, 14 Feb at 06:00 pm Chesapeake Inn & Marina

Planning Meeting

 Thu, 08 Jan at 06:00 pm Chesapeake Inn Restaurant and Marina

Just a Bit Outside @ Chesapeake Inn

 Fri, 19 Dec at 07:00 pm Chesapeake Inn

Stand Up Comedy Night

 Fri, 06 Feb at 08:30 pm Chesapeake Inn Restaurant & Marina USD 33

Stomp Box @ Chesapeake City VFW 7-11pm

 Sat, 27 Dec at 07:00 pm Chesapeake City VFW

Chesapeake City VFW

 Sat, 20 Dec at 07:00 pm Chesapeake City VFW

Holiday Sip & Shop "Between The Vines"

 Sun, 14 Dec at 12:00 pm 237 Bohemia Manor Farm Ln USD 22

Sunday Brunch With Santa & Mrs. Claus

 Sun, 21 Dec at 10:00 am 237 Bohemia Manor Farm Ln USD 29 to 45

Just a Bit Outside @ Chesapeake Inn

 Fri, 27 Feb at 07:00 pm Chesapeake Inn Restaurant and Marina

The Amigos at Baker's Restaurant

Fri, 19 Dec at 06:00 pm Baker's

Chesapeake Inn

 Sat, 20 Dec at 06:00 pm Chesapeake Inn & Marina

Just a Bit Outside @ Chesapeake Inn

 Fri, 03 Apr at 07:00 pm Chesapeake Inn Restaurant and Marina

Western Hat Bar

Fri, 20 Feb at 06:00 pm 3192 Augustine Herman Hwy Chesapeake City MD

THE EVERAFTER @ Chesapeake Inn

 Fri, 13 Feb at 07:00 pm Chesapeake Inn

Just a Bit Outside @ Chesapeake Imn

 Sat, 30 May at 01:00 pm Chesapeake Inn Restaurant and Marina

New Year’s Eve Dinner

 Wed, 31 Dec at 04:00 pm 237 Bohemia Manor Farm Lane, Chesapeake City, MD, United States, Maryland 21915

Vertigo Breeze Rockin the Chesapeake Inn

 Sun, 15 Feb at 12:00 pm Chesapeake Inn

Bubbles & Pearls New Year's Eve Party

 Wed, 31 Dec 237 Bohemia Manor Farm Ln USD 162

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

 Sat, 06 Dec at 10:00 am Chesapeake Inn Restaurant & Marina USD 28 to 47

A Date Night Adventure! - Chesapeake City Scavenger Hunt

 Sun, 11 May at 08:00 am 11 Bohemia Ave USD 36