Upcoming Chesapeake City Events

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

Stand Up Comedy Night

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

Bridgerton Ball!

 Sat, 21 Feb at 07:00 pm Sinking Springs Retreat Center, LLC

Valentine's at The Chesapeake Inn

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

Sassy Sips @ Chesapeake City St. Patrick's Day

 Sat, 14 Mar at 12:00 pm Chesapeake City Town Hall

January's Wine and Dine for the Arts

 Fri, 30 Jan at 06:00 pm Chesapeake Inn

The Sensational Soul Cruisers Dance Party & Brunch Buffet

 Sun, 15 Feb at 12:00 pm Chesapeake Inn Restaurant & Marina USD 70

Kris V and Richie D LIVE on The Deck

 Fri, 20 Feb at 07:00 pm 605 Second Street, Chesapeake City, MD, United States, Maryland 21915

Triple Rail Turn LIVE on The Deck

 Sat, 07 Feb at 07:00 pm 605 Second Street, Chesapeake City, MD, United States, Maryland 21915

Jovon Newman LIVE on The Deck

 Sat, 31 Jan at 07:00 pm 605 Second Street, Chesapeake City, MD, United States, Maryland 21915

Sip Into Winter: A Mixology Workshop

 Fri, 30 Jan at 06:00 pm 237 Bohemia Manor Farm Ln USD 87

Dueling Pianos with The Philly Keys • February 21

 Sat, 21 Feb at 08:30 pm Chesapeake Inn Restaurant & Marina USD 28 to 39

Galentine's Day Sip & Shop

 Sun, 15 Feb at 12:00 pm 237 Bohemia Manor Farm Ln USD 23

GALENTINES PARTY

 Thu, 12 Feb at 06:00 pm RummuR Lounge, Bohemia Avenue, Chesapeake City, MD, USA USD 55

Snowman Sprint Fun Run & Snow Much Fun Family Day

 Sat, 07 Feb at 01:00 pm 108 Bohemia Ave, Chesapeake City, MD 21915-1241, United States

Dueling Pianos with The Philly Keys • February 20

 Fri, 20 Feb at 08:30 pm Chesapeake Inn Restaurant & Marina USD 28 to 39

THE EVERAFTER @ Chesapeake Inn

 Fri, 13 Mar at 07:00 pm Chesapeake Inn Restaurant & Marina

Top of the Bay Business Women January Luncheon!

 Wed, 28 Jan at 11:30 am Vietri’s Cucina

The Amigos at Baker's Restaurant

Sat, 28 Feb at 06:00 pm Baker's

JUMPER LIVE on The Deck

 Fri, 30 Jan at 07:00 pm 605 Second Street, Chesapeake City, MD, United States, Maryland 21915

Chesapeake City Sip and Stroll 2026

 Sat, 21 Feb at 01:00 pm 108 Bohemia Ave USD 29

Exit 93 LIVE on The Deck

 Sat, 14 Feb at 07:00 pm 605 Second Street, Chesapeake City, MD, United States, Maryland 21915

Wine 2.0

 Tue, 03 Mar at 12:00 pm 237 Bohemia Manor Farm Ln Free

Bubbles & Brunch

 Sun, 08 Feb at 11:00 am 237 Bohemia Manor Farm Ln USD 50

Mocks & Socks

 Thu, 26 Mar at 04:30 pm Sinking Springs Retreat Center, LLC

Just a Bit Outside @ Chesapeake Inn

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

DECADE80 LIVE on The Deck

 Sat, 28 Feb at 07:00 pm 605 Second Street, Chesapeake City, MD, United States, Maryland 21915

Solecraft LIVE on The Deck

 Fri, 06 Feb at 07:00 pm 605 Second Street, Chesapeake City, MD, United States, Maryland 21915

ST PADDYS DAY PARTY March 14th @VFW Chesapeake city with Jackson Station 7-11pm

 Sat, 14 Mar at 07:00 pm VFW ChesapeakeCity

Vertigo Breeze Rockin the Chesapeake Inn

 Sun, 15 Feb at 12:00 pm Chesapeake Inn

Just a Bit Outside @ Chesapeake Imn

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

Just a Bit Outside @ Chesapeake Inn

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

Joyride @ Chesapeake Inn, Chesapeake City, MD

 Sun, 22 Mar at 12:00 pm Chesapeake Inn & Marina

Western Hat Bar

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

Just a Bit Outside @ Chesapeake Inn

 Sat, 27 Jun at 01:00 pm Chesapeake Inn Restaurant and Marina

The Everafter LIVE on The Deck

Fri, 13 Feb at 07:00 pm 605 Second Street, Chesapeake City, MD, United States, Maryland 21915

THE EVERAFTER @ Chesapeake Inn

 Fri, 13 Feb at 07:00 pm Chesapeake Inn

54th Annual MACC Awards Night

 Fri, 01 May at 06:00 pm Chesapeake Inn Restaurant and Marina

Boy Band Brunch with The Boy Band Project

 Sun, 19 Apr at 11:00 am Chesapeake Inn Restaurant & Marina USD 70

Chesapeake Inn St Pattys Day

 Sat, 14 Mar at 12:00 pm Chesapeake Inn & Marina

The FM Band LIVE on The Deck

 Sat, 21 Feb at 07:00 pm 605 Second Street, Chesapeake City, MD, United States, Maryland 21915

Just a Bit Outside LIVE on The Deck!

 Fri, 27 Feb at 07:00 pm 605 Second Street, Chesapeake City, MD, United States, Maryland 21915

Pop-Up Shop

 Sun, 08 Feb at 10:30 am 2725 Augustine Herman Hwy, Chesapeake City, MD 21915-1408, United States

Paint & Sip by Candlelight

Fri, 06 Feb at 06:00 pm Dreamview farm

Tour & Taste

 Sat, 02 Aug at 12:00 pm 237 Bohemia Manor Farm Ln USD 36