Chesapeake Festivals Events

Chesapeake Virginia Wine Festival

Chesapeake City Park 10 Oct 2026

Pull for Pink 2026

900 City Park Dr, Chesapeake, VA 23320, USA 25 Oct 2026

JUICERUN

409 Byron St 26 Sep 2026

Party in the Park

Chesapeake City Park 7 Oct 2026

PAWtoberFest: A Dog-Friendly Oktoberfest Celebration, Pet Photos + Market

Bubba's 33 26 Sep 2026

6th Annual Barktoberfest

701 River Walk Pkwy, Chesapeake, VA 23320-9200, United States 27 Sep 2026

Chesapeake Celebrates Trees

Chesapeake Arboretum 26 Sep 2026

Tidewater Highland Games

Historic Greenbrier Farms 7 Nov 2026

Mystique Fall Festival

Mystique Salon & Skin Spa 17 Oct 2026

River Walk Annual Fall Craft Fair

701 River Walk Pkwy, Chesapeake, VA 23320-9200, United States 10 Oct 2026

Pasta in the Park Waterway Market at Great Bridge Village

116 Reservation Road, Chesapeake, VA, United States, Virginia 23320 11 Oct 2026

6th Annual Fall Farm Fair Fundraiser!

444 St. Brides Rd W 24 Oct 2026

Black Ink: Literature Festival

298 Cedar Rd, Chesapeake, VA, United States, Virginia 23322 26 Sep 2026

River Walk Annual Fall Craft Fair

701 River Walk Pkwy, Chesapeake, VA 23320-9200, United States 10 Oct 2026

Día de muertos 2026

Chesapeake City Park 1 Nov 2026

Love Songs on Sunday's Fall Wellness Festival

Melanin Meadows Manor 18 Oct 2026

Fall Craft Fair

Deep Creek High School 24 Oct 2026

Friday the 13th Night Market

112 Wayne Avenue, Chesapeake, VA, United States, Virginia 23320 13 Nov 2026

Jolliff UMC Annual Fall Festival

1900 Jolliff Rd, Chesapeake, VA 23321-1404, United States 7 Nov 2026

Portsmouth Moose Craft and Vendor Fair

George Washington Hwy, Chesapeake, VA 7 Nov 2026

Tidewater Highland Games

2112 Dr Eason Rd, Chesapeake, VA 23322, United States 6 Nov 2026

8TH ANNUAL VA TAKE ME BACK BALL (HOMECOMING )

Cheasapeak, Va 7 Nov 2026

The Pixel Vault 2

725 woodlake drive chesapeake va 9 Jan 2027