Chesapeake Holiday Events

Holiday events Happening Next in Chesapeake, VA

Chesapeake Holiday Craft Show

 Chesapeake Conference Center 22 Nov 2025
CHRISTMAS-MARKETS-AND-FAIRS

Holiday Brass

 Chesapeake Conference Center 18 Dec 2025
MUSIC

The Holiday Market at Vintage Vibe

 232 Centerville Turnpike N , Chesapeake, VA, United States, Virginia 23320 22 Nov 2025
CHRISTMAS-MARKETS-AND-FAIRS

Christmas Cookie Decorating Class @ Studly Brewing

 Studly Brewing 11 Dec 2025
WORKSHOPS USD 34 TO 66

Portsmouth Moose Craft And Vendor Fair

 Portsmouth Moose Lodge 8 Nov 2025
SHOPPING

Winery Spotlight Wine Tasting: Chalk Hill

 WineStyles Chesapeake 1 Nov 2025
FOOD-DRINKS USD 39 TO 44

Sleight The Miles Holiday Run Club FREE Preview Run ( for a mini session)

 Chesapeake City Park 1 Nov 2025
HOLIDAY

Holiday Glass Tree Workshop

232 Centerville Turnpike N, Chesapeake, VA 6 Nov 2025
WORKSHOPS

"GIRL GET UP"(TaIitha Cumi )

 2401 Bainbridge Blvd, Chesapeake, VA 13 Dec 2025
HOLIDAY

Uncorked Educational Wine Tasting Class: Fall Feasts

 WineStyles Chesapeake 30 Oct 2025
WORKSHOPS USD 28 TO 34

Beginner Stained Glass Workshop

232 Centerville Turnpike N, Chesapeake, VA 20 Nov 2025
WORKSHOPS

Ricky Quinn at Triple R Ranch FALL

 Triple R Ranch 15 Nov 2025
TRIPS-ADVENTURES

Happy Holidays at the Retreat at Western Branch

 The Retreat at Western Branch - A 55+ Active Adult Community 6 Dec 2025
FREE

Holiday Tray Workshop

 232 Centerville Turnpike N , Chesapeake, VA, United States, Virginia 23320 13 Nov 2025
WORKSHOPS

South Norfolk Fall/Winter Craft Bazaar

 Buffalow Family and Friends Community Days 15 Nov 2025
NONPROFIT

Networking Lunch and Food Drive!!!

 600 Belaire Ave, Chesapeake, VA 23320-4771, United States 11 Nov 2025
HOLIDAY

BLACK FRIDAY SALE EVENT

800 South Battlefield Blvd, Chesapeake, VA. 23322 29 Nov 2025
BLACK-FRIDAY

PHUMC Pathfinders Chapter - Toy Drive

 Big Ugly Brewing 9 Nov 2025
TOY-DRIVES

PAJAMAS AND PRAISE

 SpringHill Suites by Marriott Chesapeake Greenbrier1446 Crossways Blvd Chesapeake, VA 23320 13 Dec 2025
HOLIDAY USD 30 TO 100

Christmas Mini’s

Chesapeake VA 29 Nov 2025
CHRISTMAS

The Holistic Treehouse's Christmas Market

The Holistic Treehouse 13 Dec 2025
CHRISTMAS-MARKETS-AND-FAIRS

Breakfast with Santa & Team Chesapeake 🎄🎅

 Pale Horse Coffee (Chesapeake, VA - Great Bridge) 13 Dec 2025
BREAKFAST-WITH-SANTA

Portsmouth Moose Craft And Vendor Fair

 Portsmouth Moose Lodge 8 Nov 2025
NONPROFIT

Holiday Whobilation Brunch

 Chesapeake Conference Center 14 Dec 2025
BRUNCH

Wine Tasting Wednesday

 WineStyles Chesapeake 13 Aug 2025
FOOD-DRINKS USD 12

Great Deal & Good Deed

 Norfolk Va 13 Dec 2025
HOLIDAY