Festivals in Chesapeake

Check out happening festivals events all around Chesapeake, VA

Chesapeake Virginia Wine Festival

 Sat, 11 Oct at 12:00 pm Chesapeake City Park

South Norfolk Ruritans Crab Fest 2025

 Sun, 07 Sep at 01:00 pm Chesapeake City Park USD 66

2ND Annual Ruritans Car and Craft Show

Sat, 16 Aug at 10:00 am Khedive Shrine Center

Chesapeake Princess Day

 Sat, 13 Sep at 10:00 am Chesapeake Convention Center

Back to School & Baptism Bash 2025

 Sun, 17 Aug at 10:00 am 1217 Centerville Turnpike N Free

Boots Brims & Beats

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

2nd Annual Back to School Extravaganza

Sun, 24 Aug at 10:00 am Chesapeake Christian Center

3rd Annual Rosemont Block Party

 Sat, 16 Aug at 11:00 am 3505 Bainbridge Blvd, Chesapeake, VA

The Chesapeake Sheriff's Oyster&South Festival

 Sat, 08 Nov at 01:00 pm Historic Greenbrier Farms

Oktoberfest | Big Ugly Brewing

 Fri, 26 Sep at 03:00 pm 845 Battlefield Blvd S, Chesapeake, VA, United States, Virginia 23322

Chesapeake Celebrates Trees

 Sat, 27 Sep at 12:00 pm 208 Conquest Dr, Chesapeake, VA 23322, United States

Family Fun Day!

 Sat, 30 Aug at 01:00 pm 1313 Burns Street, Chesapeake, VA, United States, Virginia 23320 Free

Renaissance Faire

Sat, 11 Oct at 11:00 am Major Hillard Library

5th Annual Barktoberfest

 Sun, 21 Sep at 11:00 am 701 River Walk Pkwy, Chesapeake, VA 23320-9200, United States

5th Annual Kars4Kids Charity Car Show

 Sun, 05 Oct at 09:00 am Chesapeake City Park

2025BacktoSchool Bookbag Giveaway Western Tidewater-First Baptist SouthHill

 Sat, 23 Aug at 11:00 am First Baptist Church South Hill Free

Cookbook Store Pop-up at Black Ink: Block Party & Lit Fest

 Sat, 20 Sep at 12:00 pm Dr. Clarence V. Cuffee Library

Fall Garden Fair and Plant Swap/Sale

 Sat, 20 Sep at 10:00 am Major Hillard Library

Chaos Leads the Freedom Ride

 Sat, 06 Sep at 10:00 am AJ Gator's - Centerville

Rock Painting & Farm Fun

 Sat, 23 Aug at 03:00 pm Chesapeake VA

Vintage Vibe’s Fall & Halloween Open House

 Sat, 06 Sep at 10:00 am 232 Centerville Turnpike N, Chesapeake, VA

3rd Quarter 2025 - KWT Pop-Up - Hey Sis, Let's Talk

 Sat, 20 Sep at 11:00 am 2101 Iowa St Free

Vibe or Die: BACK TO SCHOOL FEST Underground Local Alternative Hip Hop Rap

 Fri, 05 Sep at 07:00 pm Riff House Pub USD 7 to 13

Back to School Bash - Teacher Appreciation Edition

 Sat, 23 Aug at 09:00 am 1109 Cedar Rd, Chesapeake, VA 23322-7198, United States

Star & Stripes & Symphonies: Symphony Under the Stars in Chesapeake

Sun, 31 Aug at 07:30 pm Chesapeake City Park

Halloween Costume Reveal

 Fri, 15 Aug at 09:00 am Once Upon A Child - Chesapeake Greenbrier, VA

Reenactment of The Battle of Great Bridge

 Sun, 07 Dec at 10:00 am 120 Reservation Rd, Chesapeake, VA 23322-5234, United States

Fall Farm Fair Fundraiser

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

Pokemoon: Sailor Moon & Pokemon Market

 Sun, 14 Sep at 01:00 pm The Garage Brewery

AMBERFEST

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

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

Reenactment of The Battle of Great Bridge

 Sat, 06 Dec at 10:00 am 120 Reservation Rd, Chesapeake, VA 23322-5234, United States

Monster Fest 22

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

Bruin Blast 2025!

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

Savor the Sun: A Wine Tasting Experience

 Sun, 31 Aug at 03:00 pm 600 Belaire Ave, Chesapeake, VA, United States, Virginia 23320

The 44th Annaul Great American Food Fest

 Wed, 01 Oct at 04:00 pm Chesapeake City Park

Pink on the Green

 Sat, 27 Sep at 04:00 pm The Venue at Cahoon

Blind Equation, fallingwithscissors, Spears Of Cassius

 Mon, 25 Aug at 06:00 pm RiffHouse Pub

Tidewater Coast Guard Festival 2025

 Sat, 04 Oct at 10:00 am Greenbrier

Fall Kickoff

 Sun, 07 Sep at 10:00 am 333 Cedar Rd, Chesapeake, VA, United States, Virginia 23322

Blue Grass and Brunswick Stew

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

South Norfolk Ruritans Cars And Crafts Show

 Sat, 16 Aug at 03:00 pm Khedive Shrine Center

Zombies at Ballahack

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

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

SPS (Stiff Persons Syndrome) Awareness Car, Bike, Truck Show

 Sat, 20 Sep at 04:00 pm 1377 Bells Mill Rd. Chesapeake

Poker Run Hog Roast with Cigar and Bourbon Night

 Sat, 04 Oct at 04:00 pm American Legion post 280 Virginia

CARNIVAL & CIRCUS: Non-Stop Fun in the Big Top Week!

 Mon, 11 Aug at 08:00 am 504 Cedar Road, Chesapeake, VA, United States, Virginia 23322