Chesapeake Festivals Events

Festivals Happening Next in Chesapeake, VA

South Norfolk Ruritans Crab Fest 2025

 Chesapeake City Park 7 Sep 2025
FESTIVALS USD 66

Chesapeake Virginia Wine Festival

 Chesapeake City Park 11 Oct 2025
FESTIVALS

Chesapeake Princess Day

 Chesapeake Convention Center 13 Sep 2025
PARTIES

Vintage Vibe’s Fall & Halloween Open House

 232 Centerville Turnpike N, Chesapeake, VA 6 Sep 2025
FOOD-DRINKS

Boots Brims & Beats: A HOMECOMING PARTY

 Khedive Shrine Center 24 Oct 2025
PARTIES

The Chesapeake Sheriff's Oyster&South Festival

 Historic Greenbrier Farms 8 Nov 2025
FESTIVALS

Oktoberfest | Big Ugly Brewing

 845 Battlefield Blvd S, Chesapeake, VA, United States, Virginia 23322 26 Sep 2025
OKTOBERFEST

Chesapeake Celebrates Trees

 208 Conquest Dr, Chesapeake, VA 23322, United States 27 Sep 2025
TRIPS-ADVENTURES

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

 Dr. Clarence V. Cuffee Library 20 Sep 2025
ART

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

 2101 Iowa St 20 Sep 2025
POP-UPS FREE

Peppa's Pumpkin Patch Party

 2605 Moses Grandy Trail, Suite E, Chesapeake, VA, United States, Virginia 23323 12 Oct 2025
PARTIES

5th Annual Barktoberfest

 701 River Walk Pkwy, Chesapeake, VA 23320-9200, United States 21 Sep 2025
SPORTS

5th Annual Kars4Kids Charity Car Show

 Chesapeake City Park 5 Oct 2025
NONPROFIT

Chaos Leads the Freedom Ride

 AJ Gator's - Centerville 6 Sep 2025
NONPROFIT

Reenactment of The Battle of Great Bridge

 120 Reservation Rd, Chesapeake, VA 23322-5234, United States 6 Dec 2025

Pink on the Green

 The Venue at Cahoon 27 Sep 2025
ENTERTAINMENT

Fall Garden Fair and Plant Swap/Sale

 Major Hillard Library 20 Sep 2025

Renaissance Faire

Major Hillard Library 11 Oct 2025
SHOPPING

Pokemoon: Sailor Moon & Pokemon Market

 The Garage Brewery 14 Sep 2025
POKEMON

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

 Riff House Pub 5 Sep 2025
ENTERTAINMENT USD 7 TO 13

Bruin Blast 2025!

 Chesapeake, VA 24 Oct 2025

Reenactment of The Battle of Great Bridge

 120 Reservation Rd, Chesapeake, VA 23322-5234, United States 7 Dec 2025

The River Boyz at the Chesapeake Virginia Wine Festival!

 900 City Park Dr, Chesapeake, VA 23320, United States 11 Oct 2025
FESTIVALS

AMBERFEST

 Deep Creek Ruritan Club 4 Oct 2025
SPORTS

Monster Fest 22

 Chesapeake Public Library 4 Oct 2025
FESTIVALS

Tidewater Coast Guard Festival 2025

 Chesapeake City Park 4 Oct 2025
FESTIVALS

Fall Farm Fair Fundraiser

444 St. Brides Rd W 11 Oct 2025
NONPROFIT

Blue Grass and Brunswick Stew

 2752 S Battlefield Blvd, Chesapeake, VA, United States, Virginia 23322 25 Oct 2025
MUSIC

The 44th Annaul Great American Food Fest

 Chesapeake City Park 1 Oct 2025
FOOD-TRUCK-FESTIVALS

Fall Kickoff

 333 Cedar Rd, Chesapeake, VA, United States, Virginia 23322 7 Sep 2025
KIDS

Zombies at Ballahack

 2900 ballahack rd, Chesapeake, VA, United States, Virginia 23322 25 Oct 2025

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

 Fraternal Order of Eagles #795 18 Oct 2025
ART

WonderFALL Lantern Festival

 1901 Paramont Ave, Chesapeake, VA 23320-2466, United States 15 Nov 2025
FESTIVALS

Hickory Fall Craft Show sponsored by Hickory Band Parents

1996 Hawk Blvd, Chesapeake, VA 23322-2124, United States 15 Nov 2025
MUSIC

Fall Family Care Safety Fest

 1140 kempsville rd, Chesapeake, VA, United States, Virginia 23320 16 Oct 2025
FESTIVALS

Swarm Mob Car and Motorcycle Club SPS (Stiff Persons Syndrome) Awareness Car, Bike, Truck Show

 1377 Bells Mill Rd. Chesapeake 20 Sep 2025
CAR-SHOWS

GB Fall Festival/Halloween Party & Chili Cookoff

 The Church of Jesus Christ of Latter-day Saints 25 Oct 2025

Poker Run Hog Roast with Cigar and Bourbon Night

 American Legion post 280 Virginia 4 Oct 2025