Upcoming Chesapeake Events

Check out what's happening all around Chesapeake, VA

The 43rd Annual Chesapeake Jubilee

 Thu, 14 May at 04:00 pm 900 Greenbrier Pkwy, Chesapeake, VA 23320-3677, United States USD 10

Chesapeake Virginia Wine Festival

 Sat, 10 Oct at 12:00 pm Chesapeake City Park

Pride in the 'Peake 2026

 Sun, 14 Jun at 12:00 pm Chesapeake City Park

Mother's Day Yoga with Baby Animals (Baby goats, piglets, & lambs) May 16th

 Sat, 16 May at 09:00 am Bergey's Barnyard USD 45

Jazz Night Under the Stars: Live Band

 Fri, 15 May at 07:00 pm WineStyles Chesapeake USD 12 to 18

6th Annual Somewhere Over The Rainbow Gala

 Sat, 19 Sep at 06:00 pm Delta Hotels Chesapeake Norfolk USD 135 to 215

South Norfolk Ruritans 19th Annual Blue Crab Festival

 Sun, 13 Sep at 02:00 pm Chesapeake City Park

DJB @ The Chesapeake Jubilee

 Sun, 17 May at 03:00 pm 900 City Park Dr, Chesapeake, VA 23320, United States

4th Annual All Black-Tie Affair

 Sat, 18 Jul at 07:00 pm The Signet Center, Bells Mill Road, Chesapeake, VA, USA USD 60 to 650

Lucky Strike Chesapeake Lucky Launch Party!

 Sun, 17 May at 12:00 pm Lucky Strike Chesapeake Free

American Cancer Society Fundraiser | Relay For Life of South Hampton Roads

 Sat, 06 Jun at 02:00 pm Chesapeake City Park

MEMORIAL DAY COOKOUT

 Sun, 24 May at 04:00 pm The Venue at Cahoon Free

The Gothic Market (May 30, 2026) Chesapeake/Virginia Beach Area

 Sat, 30 May at 12:00 pm Chesapeake Conference Center | 700 Conference Center Dr, Chesapeake, VA 23320

Real Life and Rummel's Spring 2026 Car Show

 Sat, 16 May at 10:00 am Real Life Christian Church

Sunflower Fox & The Chicken Leg (with opener Brian Grilli) @ Peake Tavern in Chesapeake! (FREE SHOW)

 Sat, 23 May at 07:00 pm Peake Tavern

Cars and Coffee Norfolk @ Greenbrier Mall May Make-Up Meet

 Sat, 16 May at 09:00 am 1401 Greenbrier Pkwy, Chesapeake, VA 23320-0204, United States

CBAA Art Crawl

Sat, 06 Jun at 10:00 am Norfolk, Chesapeake, and Virginia Beach

STRONGER TOGETHER: HOPE CHALLENGE

 Sat, 13 Jun at 08:00 am Dismal Swamp Canal Trl, Chesapeake, VA 23322, United States

PromUS 2026

 Fri, 22 May at 07:00 pm The Signet Center USD 0 to 15,000

Pilates Party- Reformer Style

 Sat, 16 May at 02:00 pm Club Pilates - Greenbrier USD 75

Black Girls Shop Juneteenth Bus Tour

 Sat, 13 Jun at 08:00 am Greenbrier Mall USD 60 to 61

Michelle Runs the Eras: Benefiting H.E.R. Shelter

 Sat, 16 May at 07:00 am 741 Eden Way N, Chesapeake, VA 23320-3072, United States

2026 Freedom Fund Advocacy and Awards Gala

 Sat, 26 Sep at 05:30 pm Delta Hotels Chesapeake Norfolk USD 109 to 135

Children’s Ultimate Rave Party | Live Costumed Characters Kids Love | Da

 Sat, 03 Oct at 10:30 am 700 Conference Center Dr USD 55

Groove on the Green

 Sat, 23 May at 04:00 pm Cutlass Grille Free

RawBeeT’s Banjo Tribe @ Peake Tavern in Chesapeake!! (FREE LIVE MUSIC)

 Fri, 15 May at 07:00 pm Peake Tavern

8th Annual Southern Chevrolet Custom Car Show

Sat, 07 Nov at 10:00 am 3412 western branch blvd

Chesapeake, VA Verizon Military Appreciation Event

 Sat, 16 May at 11:00 am 1224 Greenbrier Pkwy Free

Sisters in Christ HR: Picnic in the Park

 Fri, 12 Jun at 06:00 pm Chesapeake City Park Free

Alien Invasion

Sat, 06 Jun at 07:00 pm Frightmare

It's MOOSESTOCK at Portsmouth Moose Lodge!

 Sun, 11 Oct at 03:00 pm Portsmouth Moose Lodge 898

Speedline Elite 32nd Year Anniversary Custom Car Show

 Sat, 23 May at 10:00 am Asphalt Lots 1377 Bells Mill Road Chesapeake, VA 23322

DJB @ Bucket's Bar and Grille

 Sat, 26 Sep at 08:00 pm Buckets Bar and Grill

Premium Italian Wine Tasting

 Sat, 30 May at 05:00 pm WineStyles Chesapeake USD 44 to 49

Limited - engagement screening of MULTIPLE CHOICE

 Thu, 04 Jun at 04:30 pm Chesapeake Public Schools Free

Tidewater Striders Duathlon

 Sat, 20 Jun at 07:30 am Dismal Swamp Canal Trl, Chesapeake, VA 23322, United States

Wallace Chadwick's Sheriff Invitational Golf Tournament

 Mon, 01 Jun at 08:00 am Greenbrier Country Club USD 109 to 856

Memorial Day Baptism & Cookout

 Sun, 24 May at 11:00 am Greenbrier Christian Academy Free

Chesapeake First Citizen 2026 Banquet and Award Presentation

 Thu, 17 Sep at 06:00 pm Chesapeake Conference Center

Alien Invasion!

 Sat, 06 Jun at 07:00 pm Frightmare USD 25

5th Annual Juneteenth Freedom Experience (JFX)

 Sat, 20 Jun at 10:00 am Chesapeake Central Library Free

A Home Project Planning Workshop

 Fri, 12 Jun at 01:00 pm Indian River Library Free

Love Songs on Sunday's Wellness Festival

 Sun, 17 May at 02:30 pm Melanin Meadows Manor USD 0 to 61

JUNETEETH Vendor Event at Greenbrier Mall

 Fri, 19 Jun at 10:00 am Greenbrier Mall

Train Time at the Chesapeake Public Library

 Sat, 06 Jun at 09:00 am Chesapeake Public Library

Standup Comedy at The Garage Brewery (Chesapeake, VA)

 Sat, 17 Jan at 08:00 pm The Garage Brewery USD 13

Euphoria: The Wellness Festival

 Sat, 13 Jun at 10:00 am The Barn on Baum (Dwellings Farms) USD 25 to 90

3rd Annual Pink Ride Car, Truck and Bike Show

 Sun, 27 Sep at 11:00 am Khedive Shrine Center

Spiritual Empowerment with Pastor Dr. Jamal Bryant

 Fri, 05 Jun at 07:00 pm Chesapeake Conference Center USD 0 to 215

River Walk America 250 Picnic

 Sun, 05 Jul at 11:00 am 701 River Walk Pkwy, Chesapeake, VA 23320-9200, United States

Memorial Day Celebration with The Fuzz Band

 Sat, 23 May at 04:00 pm Cutlass Grille Free

MEET ME OUTSIDE DAY PARTY

 Sat, 30 May at 04:00 pm 1201 Club House Dr USD 20

Runnin' Shine Duo at Tap It Chesapeake!

 Sat, 16 May at 08:00 pm Tap It Local-Chesapeake

Tidewater Striders Summer Series #2

 Tue, 14 Jul at 06:30 pm Chesapeake City Park

Autumn Wine Tasting

 Sat, 26 Sep at 01:00 pm 600 Belaire Ave, Chesapeake, VA, United States, Virginia 23320

Chesapeake - Virginia Concealed Carry Class - $55

 Fri, 29 May at 06:00 pm Homewood Suites by Hilton Chesapeake-Greenbrier

Foodies + New Friends: Chesapeake Dinner Club (Giving Back Edition)

 Mon, 01 Jun at 07:00 pm Luce Secondo USD 23

Strider XC Classic

 Sat, 16 May at 07:30 am Bells Mill Park

The Link Up: A Community Conversation + Dance Experience

 Sat, 18 Jul at 12:00 pm Western Branch Community Center Free

Referrals & Roasts: Pale Horse Edition

 Wed, 03 Jun at 09:00 am Pale Horse Coffee - Summit Pointe (Greenbrier) Free

Pottery Paint & Sip

 Sat, 27 Jun at 01:00 pm Southern Flair Pub House USD 45

UNCORKED: The Grape Escape - Learn about grape varietals, sip by sip!

 Sun, 31 May at 04:00 pm WineStyles Chesapeake USD 28 to 34

Job Work! Center Job Fair

 Wed, 10 Jun at 10:00 am 100 Outlaw St Free

2026 Military and Veterans Community Wellness Day

 Sat, 26 Sep at 10:00 am Chesapeake Conference Center Free

6th Annual Barktoberfest

 Sun, 27 Sep at 11:00 am 701 River Walk Pkwy, Chesapeake, VA 23320-9200, United States

Roll For A Cure | Poker Run for the American Cancer Society

 Sat, 16 May at 09:30 am Pale Horse Coffee (Chesapeake, VA - Great Bridge)

Mother’s Day 5K 🏃‍♀️💐🍻 Community Run/Walk 👟👟

 Sat, 16 May at 10:00 am 1011 Eden Way N, Chesapeake, VA

DIEGO en FUEGO (from WOAH!) @ Peake Tavern in Chesapeake!! (FREE LIVE MUSIC)

 Sun, 24 May at 07:00 pm Peake Tavern

WOMEN RUNNING 4 JESUS SNEAKER BALL 2026

 Sat, 07 Nov at 12:00 pm Solid Rock World Wide Outreach Free

KARAOKE WEDNESDAYS @ Peake Tavern in Chesapeake!!

 Wed, 20 May at 07:00 pm Peake Tavern

AWS Solution Architect Training | 4-Day Bootcamp in Chesapeake, VA

 Tue, 28 Apr at 09:00 am 1545 Crossways Blvd USD 3,999

Commitment Issues at Eagles' Nest Rockin' Country Bar!

 Sun, 24 May at 09:00 pm Eagles Nest Rockin Country Bar

A fair with Commitment Issues

 Sat, 16 May at 03:15 pm Chesapeake City Park

Community Celebration honoring Dr. Judy Jankowski

 Fri, 29 May at 05:00 pm 821 Baker Rd, Virginia Beach, VA, United States, Virginia 23462

Chesapeake- VA Concealed Carry $59

 Wed, 20 May at 06:00 pm Hampton Inn & Suites Chesapeake-Battlefield Blvd.

6th Annual Fall Farm Fair Fundraiser!

 Sat, 24 Oct at 10:30 am 444 St. Brides Rd W

CEH Certification In-Person Training in Chesapeake, VA

 Tue, 21 Apr at 09:00 am 1545 Crossways Blvd USD 2,999

DJB @ Bucket's Bar and Grill

 Sat, 29 Aug at 08:00 pm Buckets Bar and Grill

Rise Up! Rally in Chesapeake

 Sat, 16 May at 09:00 am 1308 Battlefield Blvd N, Chesapeake, VA 23320-4504, United States

KARAOKE THURSDAYS @ Peake Tavern in Chesapeake!!

 Thu, 04 Jun at 07:00 pm Peake Tavern

Menopause & Mindset A Midlife Fitness + Mindset Experience

 Wed, 20 May at 06:30 pm Riverview Wellness Free

🎤 K-POP Demon Hunters: Family Dance Party 🔥

 Sun, 17 May at 11:00 am 2605 Moses Grandy Trail, Suite E, Chesapeake, VA, United States, Virginia 23323

3rd Annual Changing Lanes Car Show

 Sat, 06 Jun at 08:30 am Cavalier Ford at Chesapeake Square USD 23 to 34

VGSR ADOPTION EVENT- PETSMART- CHESAPEAKE

 Sun, 17 May at 11:00 am 1236 Greenbrier Pkwy, Chesapeake, VA 23320-2886, United States

HRNG & Novel Grounds Networking

 Tue, 02 Jun at 10:30 am Novel Grounds - A Romance Bookstore USD 0 to 82

Roccaforte w/ Por Vida, The Criminal Saints, and Lingering Effects

 Sat, 16 May at 07:00 pm RiffHouse Pub

Signing: Sara Raasch Signing Ticket: May 24th, 6pm

 Sun, 24 May at 06:00 pm Novel Grounds USD 28

Joe Smith 2nd Annual Fall Classic Golf Fundraiser

 Mon, 26 Oct at 08:00 am Greenbrier Country Club USD 0 to 50,000

KARAOKE WEDNESDAYS @ Peake Tavern in Chesapeake!!

 Wed, 10 Jun at 07:00 pm Peake Tavern

CANCERSLUG, MR. FANG AND THE DARK TONES, TBA

 Sun, 07 Jun at 07:00 pm 2002 Bainbridge Blvd, Chesapeake, VA, United States, Virginia 23324

Gateway Show Series @ Sea Breeze Ponies

Sat, 30 May at 09:00 am Sea Breeze Ponies

Bike Ride of Historic Great Bridge

 Sat, 16 May at 12:00 pm Great Bridge Community Center

Story Book Event

 Fri, 15 May at 09:00 am 805 Battlefield Blvd N, Chesapeake, VA, United States, Virginia 23320

Christmas PAWty in July

 Sat, 11 Jul at 12:00 pm Big Ugly Brewing Free

CEH Certification Weekend Training Course in Chesapeake, VA

 Sat, 18 Apr at 09:00 am 1545 Crossways Blvd USD 2,999

Summertime Adopt-A-Thon

 Sat, 13 Jun at 10:00 am 3333 Taylor Rd., Chesapeake, VA, United States, Virginia 23321

R.I.S.E. WOMEN'S CONFERENCE SPONSORS AND VENDORS

 Sat, 18 Jul at 09:30 am Dr. Clarence V. Cuffee Community Center USD 130 to 1,069

Independent Author Book Market

 Sat, 23 May at 10:30 am Chesapeake Conference Center USD 8 to 15

WLW Strawberry Picking

 Sat, 23 May at 12:00 pm Hickory Ridge Farm Free

Negotiation Skills-Professional 1-Day Workshop | Chesapeake, VA

 Fri, 15 May at 09:00 am For venue details reach us at [email protected] USD 519 to 1,764
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