Entertainment events in Chesapeake

Check out happening entertainment events all around Chesapeake, VA

Boots Brims & Beats: A HOMECOMING PARTY

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

Adult Halloween Party | Big Ugly Brewing

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

Costumes & Cocktails Halloween Party

 Fri, 31 Oct at 10:00 pm Cutlass Grille

Day of the Dead Dance Party

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

Trunk-Or-Treat Party!

 Wed, 29 Oct at 06:00 pm 480 Kempsville Rd #109 Suite 109, Chesapeake, VA, United States, Virginia 23320

Oyster Roast at the Elks Lodge

 Sat, 22 Nov at 03:00 pm Portsmouth Elks Lodge USD 45

Gaither Vocal Band in Chesapeake

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

Hampton Roads Spartans Game Watch MSU vs. UofM Time TBD

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

OHCC Harvest Party

 Sat, 01 Nov at 11:00 am 825 Greenbrier Pkwy, Chesapeake, VA, United States, Virginia 23320

Frank's Fall Vendor Market

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

Rehab in Chesapeake

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

Peter Pan

 Sat, 01 Nov at 02:00 pm 1629 Jolliff Rd, Chesapeake, VA, United States, Virginia 23321

Branches Turns 8!

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

BOOTS ON DA GROUND: WHERE DEM BANDS AT

 Sat, 25 Oct at 12:00 pm Chesapeake Central Library Free

Holiday Brass

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

RIFFHOUSE HALLOWEEN PARTY

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

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

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

Blue Grass and Brunswick Stew

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

Costume Contest at The Hive Farm Bar & Grill

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

Halloween Wine Party & Adult Costume Contest

 Fri, 31 Oct at 06:00 pm WineStyles Chesapeake Free

WBHS Alumni BBQ

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

October 24 - 26, 2025

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

Harvest Fest 2025: Saved By His Grace

 Fri, 31 Oct at 05:00 pm First Baptist Church South Hill Free

Vintage Trixie's Burlesque Review - Phantom Follies

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

50,000 Watts: Radio Redemption with Tim Maurer

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

VIBE OR DIE PRESENTS: TRAPSGIVING II - Local Underground Alternative HipHop

 Sat, 29 Nov at 08:00 pm RiffHouse Pub USD 13

Zombies at Ballahack

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

Magic: the Gathering- Spider-Man Commander Party

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

Vibe O’Latern

 Sat, 25 Oct at 05:00 pm 1418 Poindexter St USD 7

757 Video Game Clearout

 Sat, 01 Nov at 10:00 am Chesapeake Conference Center

The Corprew Ave Foundation presents BOOTS, BRIMS, & BEATS

 Fri, 24 Oct at 06:00 pm Khedive Shrine Center USD 50

Music Bingo

 Thu, 06 Nov at 07:00 pm 1011 Eden Way N, Chesapeake, VA

Family Halloween Movie & Bowling Bash

 Fri, 31 Oct at 05:00 pm The Signet Center USD 0 to 55

Parents' Night Out: Halloween

 Fri, 24 Oct at 06:00 pm 561 Cedar Road Suite 4, Chesapeake, VA 23322

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

Hips of Horror 2025 RESERVED SEATING

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

Community Christmas Celebration 2025

 Fri, 12 Dec at 07:00 pm 640 S Battlefield Blvd, Chesapeake, VA, United States, Virginia 23322

Silly Spooky Kids Night Out

 Fri, 24 Oct at 05:30 pm 2605 Moses Grandy Trail, Suite E, Chesapeake, VA, United States, Virginia 23323

Gaither Vocal Band at Great Bridge Baptist Church

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

Throwback at Jerry's of Indian River, Chesapeake

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

Touch a Hot Mess, Regan

 Fri, 14 Nov at 08:00 pm RiffHouse Pub

Big Ugly Brewing Halloween Party w/ The Vince Kornegay Trio

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

Sunshine’s Halloween Party

 Fri, 31 Oct at 10:00 pm Level’s Lounge USD 20

Gaither Vocal Band

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

Open house trail ride!

Fri, 28 Nov at 01:00 pm 444 St. Brides Rd W

Music Bingo

 Thu, 04 Dec at 07:00 pm 1011 Eden Way N, Chesapeake, VA

Peter Pan

 Thu, 30 Oct at 07:00 pm 1629 Jolliff Rd, Chesapeake, VA, United States, Virginia 23321

Nasti Sip and Paint Norfolk / Virginia Beach

 Fri, 19 Jul at 06:00 pm Headlights Gentlemen’s Club USD 32 to 44

Ricky Quinn at Triple R Ranch FALL

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

Mystery Kit Bingo Party

 Sun, 26 Oct at 02:00 pm 712 River Hollow Ct, Chesapeake, VA 23320-7032, United States

Eagles Nest

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

Kidzville Costume Sunday

 Sun, 26 Oct at 10:00 am 4310 Indian River Rd, Ste 10, Chesapeake, VA

Idle Edsel's Six Band Scorcher

 Sat, 25 Oct at 07:00 pm RiffHouse Pub

Dark Journey Day | Big Ugly Brewing

 Fri, 28 Nov at 12:00 pm 845 Battlefield Blvd S, Chesapeake, VA, United States, Virginia 23322

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

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

Bandit LIVE at South Norfolk Moose Lodge

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

The River Boyz at The Creek! (FREE SHOW)

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

Live Music Bingo with Nate Sacks

Tue, 28 Oct at 06:30 pm 845 Battlefield Blvd S, Chesapeake, VA

Hickory High School Band Fall Craft Fair

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

Striders XC Classic

 Sun, 02 Nov at 07:30 am Bells Mill Park

Music Bingo

 Thu, 18 Dec at 07:00 pm 1011 Eden Way N, Chesapeake, VA

Christmas Eve Candlelight Service

 Wed, 24 Dec at 06:00 pm 640 S Battlefield Blvd, Chesapeake, VA, United States, Virginia 23322

Spooky Season Trivia Chesapeake

 Tue, 28 Oct at 07:00 pm 510 Belaire Ave, Chesapeake, VA 23320-4686, United States

FALL FESTIVAL

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

Parking Gaither Vocal Band

 Sat, 15 Nov Great Bridge Baptist Church

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

 Thu, 02 Oct at 08:00 pm Chesapeake Free

Gaither Vocal Band

 Sat, 15 Nov Great Bridge Baptist Church

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

Excellence Girls Club, Inc. 25th Anniversary Celebration

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

Music Bingo at Wasserhund Brewing Co. - Chesapeake

 Wed, 19 Nov at 06:30 pm 509 Belaire Ave, Chesapeake, VA 23320-4686, United States

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

Cloud 9/11 VA Royal Experience (Chesapeake Virginia 1 of 3 Locations)

 Thu, 11 Sep at 02:00 pm Kings Hookah and Restaurant USD 0 to 109

Practical Sales Skills Bootcamp - Closing Deals Made Easy! in Chesapeake

 Tue, 25 Nov at 09:00 am For venue details reach us at: [email protected] USD 641 to 748

Power Up Productivity: Smart Organization 1 Day Workshop in Chesapeake, VA

 Wed, 27 Aug at 09:00 am Regus - Chesapeake - Crossways Blvd USD 619 to 826