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 Spring Arts Festival

 Sat, 25 Apr at 10:00 am Chesapeake City Park

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

Tidewater Strider Spring Marathon and Half Marathon

 Sun, 26 Apr at 07:00 am Dismal Swamp Canal Trail

11th Annual Touch-a-Truck

 Sat, 25 Apr at 10:00 am Greenbrier Mall

Chesapeake Polish Fest

 Sat, 25 Apr at 10:00 am 536 Homestead Rd , Chesapeake, VA, United States, Virginia

HRNG Mother's Day Tea Party with Fallon F. Whidden, Esq.

 Thu, 07 May at 11:30 am When Skies Are Grey Photography Media & Designs USD 29 to 45

2026 Spring Plant Sale

 Sat, 25 Apr at 08:00 am Warren Farms

South Norfolk Ruritans 19th Annual Blue Crab Festival

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

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

The Jesus Tent Revival - Chesapeake, VA - May 1-3, 2026

 Fri, 01 May at 07:30 pm Bible World—An Apostolic Church

Real Life and Rummel's Spring 2026 Car Show

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

🦞 Cousins Maine Lobster at Chesapeake Spring Arts Festival 🔥

 Sat, 25 Apr at 10:00 am Chesapeake City Park

Opening Day Waterway Market at Great Bridge Village

 Sun, 26 Apr at 11:00 am 112 Reservation Road, Chesapeake, VA, United States, Virginia 23320

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

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

DERBY PARTY!

 Sat, 02 May at 04:00 pm 600 Belaire Ave, Chesapeake, VA, United States, Virginia 23320

2026 Spring Plant Sale

 Fri, 24 Apr at 08:00 am 125 Peaceful Rd, Chesapeake, VA 23322-2243, United States

CBAA Art Crawl

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

Shobou Con

Sat, 02 May at 10:00 am 298 Cedar Rd, Chesapeake, VA, United States, Virginia 23322

4th Annual All Black-Tie Affair

 Sat, 18 Jul at 07:00 pm The Signet Center, Bells Mill Road, Chesapeake, VA, USA USD 66 to 695

5th Annual Operation Military Families

Sat, 25 Apr at 11:00 am Grassfield High School

MEMORIAL DAY COOKOUT

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

STRONGER TOGETHER: HOPE CHALLENGE

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

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

 Sat, 23 May at 07:00 pm Peake Tavern

Cinco De Mayhem!

 Sat, 02 May at 07:00 pm Frightmare USD 25

Cars and Coffee Chesapeake

 Sat, 09 May at 08:00 am Everbowl Acai Bowls

Speedline Elite 32nd Year Anniversary Custom Car Show

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

Standup Comedy at The Garage Brewery (Chesapeake, VA)

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

Lucky Strike Western Branch Lucky Launch Party!

 Sun, 26 Apr at 12:00 pm Lucky Strike Western Branch Free

Line Dancing on the Lawn

 Sat, 25 Apr 225 Sign Pine Rd, Chesapeake, VA, United States, Virginia 23322

Bucket's Bar and Grille - Chesapeake, VA

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

PromUS 2026

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

Moo and More! The Williamson Farmhouse Grand Reopening

 Fri, 24 Apr at 04:00 pm Chesapeake Arboretum

BikeFest

 Sun, 03 May at 01:00 pm 1246 Dismal Swamp Canal Trail

It's MOOSESTOCK at Portsmouth Moose Lodge!

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

"Peace at the Beach"

 Fri, 24 Apr at 06:30 pm Hickory United Methodist Church

Tidewater Striders Duathlon

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

Black Girls Shop Juneteenth Bus Tour

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

Mother’s Day Brunch

 Sun, 10 May at 10:00 am 2125 Starmount Parkway Ste 105, Chesapeake, VA

One Spring to Rule Them All

 Sun, 26 Apr at 01:00 pm 1011 Eden Way N, Chesapeake, VA

Run to Breathe 5k

 Sat, 02 May at 09:00 am Dismal Swamp Canal Trl, Chesapeake, VA 23322, United States

Chesapeake First Citizen 2026 Banquet and Award Presentation

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

UNCORKED: Curds & Corks — The Art of Wine & Cheese Pairing

 Sun, 26 Apr at 04:00 pm WineStyles Chesapeake USD 34 to 39

Pop-Up Robert Mondavi Wine Tasting

 Fri, 24 Apr at 05:00 pm 600 Belaire Ave, Chesapeake, VA, United States, Virginia 23320

Win Arlo's Shed 6th and FINAL Stop

 Sat, 25 Apr at 11:00 am 110 Gainsborough Sq, Chesapeake, VA 23320, United States

Striders Dismal Swamp 5 Miler and Kid's 1 Mile

 Sat, 25 Apr at 08:00 am Dismal Swamp Canal Trail

3 Decades, 70’80’s90’sThrowBackParty

 Sat, 25 Apr at 08:00 pm Gala's Signature Events

2026 Freedom Fund Advocacy and Awards Gala

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

Run for the Roses Kentucky Derby Party

Sat, 02 May at 04:30 pm 4060 S. Military Hwy, Chesapeake, VA

Walk with Purpose: Empowering Women’s Outdoor Walk & Wellness Meetup

 Sat, 25 Apr at 10:00 am Chesapeake City Park Free

JUNETEETH Vendor Event at Greenbrier Mall

 Fri, 19 Jun at 10:00 am Greenbrier Mall

Lorcana Winterspell Set Championship

 Sat, 25 Apr at 11:00 am 3591 Forest Haven Lane, Chesapeake, VA, United States, Virginia 23321

River Walk America 250 Picnic

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

Dogs in the Drive-Thru

 Sat, 25 Apr at 12:00 pm 205 Carmichael Way, Chesapeake, VA 23322

Art Rowe & Ed Allen - Brothers Atlantic Acoustic Duo @ Tap-It Local

 Sat, 23 May at 07:00 pm Tap It Local Chesapeake

Ghost Hunt - April 23rd, 2026

 Thu, 23 Apr at 07:00 pm 112 Wayne Avenue, Chesapeake, VA, United States, Virginia 23320

Dirt Melt Live at Riffhouse Pub w/At the Stars and Crack Fox

 Sat, 06 Jun at 07:00 pm RiffHouse Pub

SALT at AJ Gators Centerville

Sat, 23 May AJ Gator's - Centerville

Village Family Presents Skate for a Cause

Sun, 03 May at 06:00 pm Greenbrier Family Skating Center Roller Skating USD 10

Liquid Relic @ RiffHouse Pub

 Sat, 30 May at 09:00 pm RiffHouse Pub

Bungee 5K Fundraiser for Communication Access!

Sat, 25 Apr at 08:00 am Ascend Bungee Fitness

Wallace Chadwick's Sheriff Invitational Golf Tournament

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

Bucket's Bar and Grill - Chesapeake, VA

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

6th Annual Barktoberfest

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

3rd Annual Pink Ride Car, Truck and Bike Show

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

April Community Book Club Meet-up

 Thu, 30 Apr at 06:00 pm Lockside Bar & Grill

Euphoria: A Community Wellness Festival

 Sat, 02 May at 09:00 am Chesapeake Conference Center USD 25 to 90

Strider XC Classic

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

LIT and SAFE VA Bounce: SKATE FOR THE CAUSE

 Sun, 03 May at 06:00 pm Greenbrier Family Skating Center USD 0 to 15,000

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

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

Nurture & Bloom: Spiritual Day Retreat - Chesapeake, VA

 Sat, 09 May at 11:00 am The Holistic Treehouse

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

 Sat, 16 May at 07:00 pm RiffHouse Pub

Mood Walk: Move. Breathe. Connect.

 Mon, 27 Apr at 06:15 pm Oak Grove Lake Park

10th Annual ADHD Symposium

 Sat, 25 Apr at 08:00 am 821 Baker Rd, Virginia Beach, VA, United States, Virginia 23462

Bike Ride of Historic Great Bridge

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

Autumn Wine Tasting

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

Love Songs on Sunday's Wellness Festival

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

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

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

Tarot 101 Activation Series with Mackenzie Foster

 Thu, 23 Apr at 06:30 pm The Holistic Treehouse

Chariots for Christ Car Show

 Sat, 09 May at 09:00 am Grassfield High School Free

One Piece Pirate's Party

 Sun, 03 May at 11:00 am 3591 Forest Haven Lane, Chesapeake, VA, United States, Virginia 23321

Tidewater Striders Summer Series #2

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

Chesapeake - Virginia Concealed Carry Class - $55

 Fri, 24 Apr at 06:00 pm Homewood Suites by Hilton Chesapeake-Greenbrier

Cinco de Mayo Cookie Decorating Class @ Studly Brewing

 Sun, 03 May at 12:30 pm Studly Brewing USD 34 to 66

Yard Sale Benefiting the American Cancer Society | Relay For Life of South Hampton Roads

 Sat, 25 Apr at 08:00 am CR Management

Chesapeake- VA Concealed Carry $59

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

Rooted and Adorned Workshop

 Sat, 09 May at 10:00 am New Life Church- Deep Creek Campus USD 130

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)

Return of Vibe or Die Underground Alternative Hip-Hop Rnb Showcase

 Sat, 02 May at 06:00 pm RiffHouse Pub USD 7 to 29

ACLS Provider

 Wed, 29 Apr at 09:00 am 809 Greenbrier Pkwy, Chesapeake, VA, United States, Virginia 23320

NEW Soft Launch of FIT4MOM Sip and Strides Casual Walk with FIT4MOM Southwest Chesapeake

Thu, 23 Apr at 09:30 am Chesapeake City Park

CEH Certification In-Person Training in Chesapeake, VA

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

ONLY for HER at Greenbrier Mall

 Fri, 08 May at 10:00 am Greenbrier Mall

FIT4MOM Scarf Magical Movement Chesapeake City Park

 Fri, 22 May at 10:30 am Chesapeake City Park

757 Is For Wellness

 Sun, 17 May at 10:00 am Abracadabra Salon

Paul Hobbs: Worldwide Wine Dinner

 Sat, 25 Apr at 05:30 pm 600 Belaire Ave, Chesapeake, VA, United States, Virginia 23320

Bloom & Thrive Wellness Expo

 Thu, 23 Apr at 04:00 pm 1508 Volvo Pkwy, Chesapeake, VA, United States, Virginia 23320

Spiritual Empowerment with Pastor Dr. Jamal Bryant

 Fri, 05 Jun at 07:00 pm Chesapeake Conference Center Free

🧭Adventures on the Northwest River

Thu, 14 May at 08:00 am Bob's Fishing hole
Categories
Live Music
Bingo
Festivals
Food & Drinks
Concerts
Car Shows
Shopping
Wine Tasting
Meet & Greet
Karaoke
Kentucky Derby
Popular topics
Education
Entrepreneurship
Motorcycling
Mindfulness
Plants
Marketing
Gardening
Leadership
Skills Upgradation
Animals
Barbeque
Running
Shopping
Beer
Branding