Entertainment events in Chesapeake

Check out happening entertainment events all around Chesapeake, VA

Chesapeake Holiday Craft Show

 Sat, 22 Nov at 10:00 am Chesapeake Conference Center

Boots Brims & Beats: A HOMECOMING PARTY

 Fri, 24 Oct at 06:00 pm Khedive Shrine Center

Live Concert Recording

 Sat, 04 Oct at 06:00 pm New Light Church- The City of Praise USD 18 to 29

Adult Halloween Party | Big Ugly Brewing

 Sat, 25 Oct at 05:00 pm 845 Battlefield Blvd S, Chesapeake, VA, United States, Virginia 23322

Day of the Dead Dance Party

 Sat, 01 Nov at 07:00 pm 112 Wayne Avenue, Chesapeake, VA, United States, Virginia 23320

Monster Fest 22

 Sat, 04 Oct at 09:00 am Chesapeake Public Library

Piggy's Pumpkin Patch Party

 Sun, 12 Oct at 01:00 pm 2605 Moses Grandy Trail, Suite E, Chesapeake, VA, United States, Virginia 23323

The River Boyz at the Chesapeake Virginia Wine Festival!

 Sat, 11 Oct at 01:00 pm 900 City Park Dr, Chesapeake, VA 23320, United States

Gaither Vocal Band in Chesapeake

 Sat, 15 Nov at 06:00 pm Great Bridge Baptist Church

Rehab in Chesapeake

 Sun, 22 Feb at 07:00 pm Riff House Pub

Princess Tea Party

 Sat, 11 Oct at 11:00 am StoneBridge School

Fire Prevention Week Kick Off - Firehouse Movie Night

 Fri, 03 Oct at 06:30 pm 3460 Battlefield Blvd S, Chesapeake, VA 23322-2401, United States

Branches Turns 8!

Fri, 21 Nov at 01:00 pm 2125 Starmount Parkway Ste. 105, Chesapeake, VA

Jo Koy Tickets

Sat, 11 Oct at 08:00 pm Ted Constant Center, Norfolk, VA

50,000 Watts: Radio Redemption with Tim Maurer

 Sat, 01 Nov at 03:00 pm 525 Kempsville Rd USD 12 to 17

Costume Contest at The Hive Farm Bar & Grill

 Fri, 24 Oct at 07:00 pm 225 Sign Pine Rd, Chesapeake, VA

The River Boyz at The Creek! (FREE SHOW)

 Fri, 03 Oct at 08:00 pm 1245 Cedar Rd, Chesapeake, VA 23322-7141, United States

Chesapeake Humane Society's Rewind To The 90's Gala 2025

Sat, 08 Nov at 06:00 pm 845 S Battlefield Blvd, Chesapeake, VA 23322

KARAOKE THURSDAYS @ The Creek in Chesapeake!!

 Thu, 02 Oct at 07:00 pm The Creek

5th Annual SkeleCon â™± Halloween Party

 Fri, 17 Oct at 06:00 pm 1011 Eden Way N, Chesapeake, VA

Gaither Vocal Band at Great Bridge Baptist Church

 Sat, 15 Nov at 06:00 pm Great Bridge Baptist Church

Gaither Vocal Band

 Fri, 14 Nov at 07:00 pm Great Bridge Baptist Church

Game Watch Party - VT v. Wake Forest

 Sat, 04 Oct at 12:45 pm Bubba's 33 - Chesapeake, VA (Chesapeake, VA - 1725 Debaun Avenue)

Hampton Roads Spartans Game Watch MSU vs. UofM Time TBD

 Sat, 25 Oct at 07:30 pm Bubba's 33 Free

Tarot Tea Party

 Sun, 12 Oct at 01:00 pm 112 Wayne Avenue, Chesapeake, VA, United States, Virginia 23320

SURVEY SAYS Game Played @ The Creek in Chesapeake!!

 Tue, 30 Sep at 07:00 pm The Creek

A Symphony Of Dreams Adult Prom

 Sat, 01 Nov at 06:00 pm Chesapeake Conference Center

October 24 - 26, 2025

 Fri, 24 Oct at 07:00 pm Bruin Drive, Chesapeake, VA

Music Bingo

 Thu, 02 Oct at 07:00 pm 1011 Eden Way N, Chesapeake, VA

The Haunted Night Market

 Fri, 10 Oct at 06:00 pm 112 Wayne Avenue, Chesapeake, VA, United States, Virginia 23320

Foxglove @ The Creek

 Fri, 17 Oct at 08:00 pm Creek Bar

WBHS Alumni BBQ

 Sat, 25 Oct at 04:00 pm Portsmouth Elks Lodge USD 23

Apple Festival

 Sat, 18 Oct at 05:00 pm 513 Johnstown Rd, Chesapeake, VA, United States, Virginia 23322

Fall Farm Fair Fundraiser

Sat, 11 Oct at 10:30 am 444 St. Brides Rd W

DaddyG Salsa Stand - Big Ugly Brewing, Chesapeake

 Fri, 10 Oct at 03:00 pm Big Ugly Brewing

Big Ugly Brewing Halloween Party w/ The Vince Kornegay Trio

 Sun, 26 Oct at 02:00 pm Big Ugly Brewing

Hips of Horror 2025 RESERVED SEATING

 Sat, 01 Nov at 06:30 pm TBD USD 23 to 28

AMBERFEST

 Sat, 04 Oct at 03:00 pm Deep Creek Ruritan Club

Ricky Quinn at Triple R Ranch FALL

 Sat, 15 Nov at 09:00 am Triple R Ranch

Shaggers @ Heart 2026 Event Package for Two Raffle Tickets Available Now - Drawing October 18, 2025

 Sat, 18 Oct at 08:00 pm Fraternal Order of Eagles #795

Magic: the Gathering- Spider-Man Commander Party

 Fri, 24 Oct at 07:00 pm 3591 Forest Haven Lane, Chesapeake, VA, United States, Virginia 23321

Music BINGO Night at Big Ugly Brewing

 Wed, 22 Oct at 06:30 pm Big Ugly Brewing

Grand Opening Party – North Beach Plastic Surgery Chesapeake Location

 Fri, 10 Oct at 04:00 pm 1401 Kristina Way Free

Field of Screams

 Sat, 18 Oct at 10:00 pm 1296 South Battlefield Boulevard, Suite 108

KARAOKE WEDNESDAYS @ The Creek in Chesapeake!!

 Wed, 01 Oct at 07:00 pm The Creek

Vintage Trixie's Burlesque Review - Phantom Follies

 Fri, 14 Nov at 07:00 pm 112 Wayne Avenue, Chesapeake, VA, United States, Virginia 23320

Holiday Brass

 Thu, 18 Dec at 06:00 pm Chesapeake Conference Center

Blue Grass and Brunswick Stew

 Sat, 25 Oct at 12:00 pm 2752 S Battlefield Blvd, Chesapeake, VA, United States, Virginia 23322

RIFFHOUSE HALLOWEEN PARTY

 Fri, 24 Oct at 07:30 pm 2002 Bainbridge Blvd, Chesapeake, VA, United States, Virginia 23324

Hickory Fall Craft Show sponsored by Hickory Band Parents

Sat, 15 Nov at 09:00 am 1996 Hawk Blvd, Chesapeake, VA 23322-2124, United States

Frank's Fall Vendor Market

Sun, 02 Nov at 10:00 am Frank's Trucking Center

Throwback at Jerry's of Indian River, Chesapeake

 Sat, 08 Nov at 08:00 pm Jerry's of Indian River

Horror Movie Trivia Night at Woody's!

 Thu, 02 Oct at 06:00 pm Big Woody's Bar and Grill

Jerry's Restaurant & Lounge, 1102 Sparrow Rd, Chesapeake, VA 23325

Sat, 06 Dec at 08:00 pm Jerry's Restaurant & Lounge, 1102 Sparrow Rd, Chesapeake, VA 23325

Vince Lee & The Hustle Shuffle with Brittany Pettit at Avalon Pier

 Sat, 22 Nov at 08:00 pm Avalon Pier, Kill Devil Hills NC

Zombies at Ballahack

 Sat, 25 Oct at 07:00 am 2900 ballahack rd, Chesapeake, VA, United States, Virginia 23322

Free Outdoor Cello Performance with Rebecca Gilmore

 Fri, 17 Oct at 12:00 pm 308 Cedar Lakes Drive, Chesapeake, VA 23322

City of Chesapeake Holiday Craft Show

 Sat, 22 Nov at 10:00 am Chesapeake Conference Center

Loyal Order of Water Buffalo Degree

 Sat, 18 Oct at 08:00 am 645 Woodlake Dr, Chesapeake, VA, United States, Virginia 23320

Pumpkin Painting

 Sun, 19 Oct at 02:00 pm 2605 Moses Grandy Trail, Suite E, Chesapeake, VA, United States, Virginia 23323

Bandit LIVE at South Norfolk Moose Lodge

Sat, 20 Dec at 07:00 pm Lodge 464 - South Norfolk

Eagles Nest

Sat, 08 Nov at 09:30 pm Eagle's Nest

🎉Homecoming/Reunion After Party🎉

 Fri, 17 Oct at 08:00 pm Bad Habits Wing & Oyster Bar

The River Boyz at The Creek! (FREE SHOW)

 Fri, 12 Dec at 08:00 pm 1245 Cedar Rd, Chesapeake, VA 23322-7141, United States

Hickory High School Bank Fall Craft Fair

 Sat, 15 Nov at 09:00 am 1996 Hawk Blvd, Chesapeake, VA 23322-2124, United States

Howl-O-Ween spooktacular party

Tue, 21 Oct at 08:00 am Great Bridge

FALL FESTIVAL

Sat, 08 Nov at 09:00 am 4420 East Rd, Chesapeake, VA 23321-2612, United States

Powerful Voices Open Mic Show - Live Music, Comedy, Poetry+ More!

 Thu, 02 Oct at 08:00 pm Chesapeake Free

Book Signing - Author Jessica Jackson

 Sat, 11 Oct at 12:00 pm Novel Grounds Free

Book Signing - Author Kate Cunningham

 Sat, 25 Oct at 12:00 pm Novel Grounds Free

REV

 Sat, 13 Dec at 07:00 am 2900 ballahack rd, Chesapeake, VA, United States, Virginia 23322

Trunk-or-Treat Family Halloween | Big Ugly Brewing

 Sun, 26 Oct at 01:00 pm 845 Battlefield Blvd S, Chesapeake, VA, United States, Virginia 23322

Excellence Girls Club, Inc. 25th Anniversary Celebration

 Sat, 08 Nov at 10:00 am Chesapeake Conference Center

Ignite Your Leadership: Lead Teams to Success Workshop in Chesapeake, VA

 Fri, 30 May at 09:00 am Regus - Chesapeake - Crossways Blvd USD 619 to 826

Gail Harts Performing Arts Fall Dance Series

 Sun, 14 Sep at 01:00 pm 2211 S Military Hwy USD 15 to 34

Return to Wholeness - A Breath, Music & Energy Workshop

 Thu, 20 Mar at 09:00 am Chesapeake Virtual via Zoom Free