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

Boots Brims & Beats: A HOMECOMING PARTY

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

The Chesapeake Sheriff's Oyster&South Festival

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

Tidewater Coast Guard Festival 2025

 Sat, 04 Oct at 10:00 am Chesapeake City Park

The 44th Annaul Great American Food Fest

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

Monster Fest 22

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

Piggy's Pumpkin Patch Party

 Sun, 12 Oct at 01:00 pm 2605 Moses Grandy Trail, Suite E, Chesapeake, VA, United States, Virginia 23323

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

5th Annual Kars4Kids Charity Car Show

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

Bruin Bash 2025!

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

Reenactment of The Battle of Great Bridge

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

Pet Costume Contest at Historic Greenbrier Farms

 Sat, 18 Oct at 10:00 am 225 Sign Pine Rd, Chesapeake, VA

Mount Pleasant Farms Fall Festival Weekends

 Sat, 04 Oct at 10:00 am 2201 Mount Pleasant Rd, Chesapeake, VA

Renaissance Faire

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

Apple Festival

 Sat, 18 Oct at 05:00 pm 513 Johnstown Rd, Chesapeake, VA, United States, Virginia 23322

Fall Farm Fair Fundraiser

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

Fall Fest 2025

 Sat, 04 Oct at 12:00 pm 4316 Bruce Rd, Chesapeake, VA, United States, Virginia 23321

Oktoberfest in Chesapeake

 Sat, 04 Oct at 11:00 am 510 Belaire Ave, Chesapeake, VA 23320-4686, United States

Reenactment of The Battle of Great Bridge

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

Trick or Treat on the Farm!

Sat, 25 Oct at 12:00 pm 225 Sign Pine Rd, Chesapeake, VA

AMBERFEST

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

Costume Contest at Historic Greenbrier Farms

 Sun, 26 Oct at 12:00 pm 225 Sign Pine Rd, Chesapeake, VA

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

Celebrate Fall with Me at Our Fun Festival!

 Sat, 04 Oct at 04:00 pm Lilley Farms

mount Pleasant Farms Fall Festival Weekends

 Sun, 05 Oct at 10:00 am 2201 Mount Pleasant Rd, Chesapeake, VA

Hometown Harvest At The Deep Creek Campus

 Sat, 25 Oct at 11:00 am 250 Mill Creek Pkwy, Chesapeake, VA, United States, Virginia 23323

Fall Festival

 Sat, 25 Oct at 05:00 pm 3505 Bainbridge Blvd, Chesapeake, VA, United States, Virginia 23324

Blue Grass and Brunswick Stew

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

Hickory Fall Craft Show sponsored by Hickory Band Parents

Sat, 15 Nov at 09:00 am 1996 Hawk Blvd, Chesapeake, VA 23322-2124, United States

Makes My Blood Dance Z3r02LGHT$p33D! Fest @ Riffhouse

 Sun, 23 Nov at 06:00 pm RiffHouse Pub USD 18

Zombies at Ballahack

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

WonderFALL Lantern Festival

 Sat, 15 Nov at 03:30 pm 1901 Paramont Ave, Chesapeake, VA 23320-2466, United States

Fall Family Care Safety Fest

 Thu, 16 Oct at 10:00 am 1140 kempsville rd, Chesapeake, VA, United States, Virginia 23320

Relay For Life Annual Fall Craft Fair

 Sat, 04 Oct at 09:00 am Chesapeake First Church of the Nazarene

FALL FESTIVAL

Sat, 08 Nov at 09:00 am 4420 East Rd, Chesapeake, VA 23321-2612, United States

GB Fall Festival/Halloween Party & Chili Cookoff

 Sat, 25 Oct at 12:00 am The Church of Jesus Christ of Latter-day Saints

Poker Run Hog Roast with Cigar and Bourbon Night

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