Chesapeake Festivals Events

Chesapeake Virginia Wine Festival

Chesapeake City Park 11 Oct 2025

South Norfolk Ruritans Crab Fest 2025

Chesapeake City Park 7 Sep 2025

2ND Annual Ruritans Car and Craft Show

Khedive Shrine Center 16 Aug 2025

Back to School & Baptism Bash 2025

1217 Centerville Turnpike N 17 Aug 2025

Chesapeake Princess Day

Chesapeake Convention Center 13 Sep 2025

Boots Brims & Beats

Khedive Shrine Center 24 Oct 2025

The Chesapeake Sheriff's Oyster&South Festival

Historic Greenbrier Farms 8 Nov 2025

Oktoberfest | Big Ugly Brewing

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

Family Fun Day!

1313 Burns Street, Chesapeake, VA, United States, Virginia 23320 30 Aug 2025

Renaissance Faire

Major Hillard Library 11 Oct 2025

Chesapeake Celebrates Trees

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

5th Annual Kars4Kids Charity Car Show

Chesapeake City Park 5 Oct 2025

2025BacktoSchool Bookbag Giveaway Western Tidewater-First Baptist SouthHill

First Baptist Church South Hill 23 Aug 2025

5th Annual Barktoberfest

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

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

Dr. Clarence V. Cuffee Library 20 Sep 2025

Chaos Leads the Freedom Ride

AJ Gator's - Centerville 6 Sep 2025

Rock Painting & Farm Fun

Chesapeake VA 23 Aug 2025

3rd Annual Rosemont Block Party

3505 Bainbridge Blvd, Chesapeake, VA 16 Aug 2025

Fall Garden Fair and Plant Swap/Sale

Major Hillard Library 20 Sep 2025

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

2101 Iowa St 20 Sep 2025

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

Riff House Pub 5 Sep 2025

Back to School Bash - Teacher Appreciation Edition

1109 Cedar Rd, Chesapeake, VA 23322-7198, United States 23 Aug 2025

Reenactment of The Battle of Great Bridge

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

Fall Farm Fair Fundraiser

444 St. Brides Rd W 11 Oct 2025

Pokemoon: Sailor Moon & Pokemon Market

The Garage Brewery 14 Sep 2025

Cuffee Center Community Celebration

2019 Windy Rd, Chesapeake, VA 23324-3739, United States 23 Aug 2025

AMBERFEST

Deep Creek Ruritan Club 4 Oct 2025

The River Boyz at the Chesapeake Virginia Wine Festival!

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

Halloween Costume Reveal

Once Upon A Child - Chesapeake Greenbrier, VA 15 Aug 2025

2nd Annual Back to School Extravaganza

Chesapeake Christian Center 24 Aug 2025

Monster Fest 22

Chesapeake Public Library 4 Oct 2025

Reenactment of The Battle of Great Bridge

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

Savor the Sun: A Wine Tasting Experience

600 Belaire Ave, Chesapeake, VA, United States, Virginia 23320 31 Aug 2025

Bruin Blast 2025!

Chesapeake, VA 24 Oct 2025

The 44th Annaul Great American Food Fest

Chesapeake City Park 1 Oct 2025

Blind Equation, fallingwithscissors, Spears Of Cassius

RiffHouse Pub 25 Aug 2025

Pink on the Green

The Venue at Cahoon 27 Sep 2025

Fall Kickoff

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

Blue Grass and Brunswick Stew

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

South Norfolk Ruritans Cars And Crafts Show

Khedive Shrine Center 16 Aug 2025

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

Poker Run Hog Roast with Cigar and Bourbon Night

American Legion post 280 Virginia 4 Oct 2025

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

504 Cedar Road, Chesapeake, VA, United States, Virginia 23322 11 Aug 2025