The holiday season is filled with cheerful and bright fun events in Hampton. Keep reading to learn about festive winter events to get you in the holiday spirit. 

Bodacious Bazaar

November 7 – 9, 2025 at the Hampton Roads Convention Center

Knock out your holiday gift shopping early, with a plethora of goods to choose from! The bi-annual Bodacious Bazaar at the Hampton Roads Convention Center will feature 350 quality vendors, artists, crafters, local businesses, and wonderful Virginia wineries all weekend long.

Whimsical Winter Wonderland

Nov. 22, 2025 at the Hampton Coliseum

This FREE event will transform the Hampton Coliseum into a festive wonderland with fun for the whole family. There will be stage shows by aerialists, jugglers and illusionists in addition to roaming entertainers and stilt walkers. There will be ample opportunities for photos in the various photo booths and holiday-themed areas. In addition, there will be face painting, balloon and glitter tattoo artists.

Holiday & Kwanzaa Marketplace

Dec. 4-6, 2025 at Hampton University Museum

Don’t miss this opportunity to get a jump on your holiday shopping! Choose from a variety of handcrafted items and artwork. Plan on coming out to our historic location and supporting local craftsmen and artisans while experiencing the museum’s current art exhibitions. Plan your shopping trip around the activity schedule, which includes programming like the History of Kwanzaa, fashion show, Steppin’ With Purpose, and art workshops.

Santa’s Attic

Dec. 5, 2025 from 10 am – 5 pm at City Hall

The Hampton Department of Parks, Recreation & Leisure Services presents its annual Santa’s Attic Arts and Crafts Show every December. Shop one-of-a-kind, hand-crafted items made by local artisans. Grab-and-go lunch and holiday treats will be available for purchase. Admission is free.

Phoebus Holiday Illumination & Craft Market

Dec. 6, 2025 on Mellen St in Phoebus

Kick off the holiday season in Historic Downtown Phoebus! Join us in the County/Hope Street Parking Lot (behind the Phoebus Library) for a cozy community celebration filled with festive cheer. Stick around as we light up the Phoebus Christmas tree at dusk and spread some holiday magic together.

Hampton Holly Days Parade

Dec. 6, 2025 Step-off at 5 p.m. in Downtown Hampton

 

Join us along Settlers Landing and the surrounding Downtown streets again as the longest-running illuminated holiday parade on the Peninsula continues.

Jane Monheit: The Merriest

Dec. 6, 2025 at The American Theatre

An Unforgettable Jazzy Christmas! The GRAMMY-nominated jazz vocalist with the silken voice, and masterful sense of swing returns with a concert celebrating Christmas and holiday favorites!

Hampton for the Holidays: 12 Days of Yule, Hearth & Herald

Dec. 12, 2025 at the Hampton History Museum

Experience the spirit of Yule through story, song, and community with Msesippi’s Tornado Bait and friends! The evening features Anita Darling, Lori Creek, and Esmeralda from Visual Artistry Entertainment, with Eric Quintin performing traditional Taiko Japanese drumming. Humorist Anthony Burcher, U Rock Art, Harold the Magician, Imara Gabe Diaz and Tornado Bait each bring their own artistry to this night with reflections on the magic, joy, and renewal of the winter solstice. Storyteller, former WVEC talent, Joe Flanagan reads an original holiday story written by Hampton City Communications Coordinator Mike Holtzclaw, and Unk Al joins Msesippi as Winter’s Trickster, closing the night in a shared celebration of community and the return of light.

Grand Holiday Bazaar

Dec. 12-14, 2025 at the Hampton Roads Convention Center

The go-to Holiday Market for all your Holiday shopping needs with over 200 vendors! General Admission: $5

Hampton Holiday Fine Arts Bazaar

Dec. 13 & 14, 2025 at The Charles H Taylor Visual Arts Center

Join us for the 4^th annual Hampton Holiday Fine Arts Bazaar. The opening of the Small Works Exhibition will be accompanied by this free two-day fine arts bazaar featuring original, handmade works from artists around the region. Come meet the artists and shop for extra special holiday gifts!

Downtown Hampton Lighted Boat Parade

Dec. 13, 2025 at the Downtown Waterfront

The Hampton River will come to life as a fleet of decorated boats parade past the waterfront. Santa will arrive by boat to take pictures with you, and live music, holiday treats and kids’ activities will be available all day long! Free and open to the public.

Hampton Roads Philharmonic: Holiday Classics!

Dec. 14, 2025 at The American Theatre

It’s An Orchestral Christmas! Familiar and new composers alike featured as well as commissioned new works make for an unforgettable afternoon! Steven Brindle, conductor.

Winter Whimsy at the Hampton Carousel

TBA at the Hampton Carousel

Make new holiday memories while enjoying the historic Hampton Carousel decked out for the season, along with classic holiday tunes. Rides $1. Closed Mondays, Thanksgiving and Christmas.

NYE Live!: New Years Eve Hampton

Dec. 31, 2026 at PBR Hampton Roads

Join us for Hampton’s BEST New Year’s Eve celebration at PBR Hampton. Ring in the new year with live entertainment, games, giveaways, champagne toast, and a $1,500 balloon drop at midnight!

New Year’s Eve Crab Pot Drop

Dec. 31, 2026 at Downtown Hampton

Looking for a unique and unforgettable way to celebrate New Year’s Eve? Head to Downtown Hampton for a night full of excitement, entertainment, and community fun.

NYE Woah 90s at THE VANGUARD Brewpub in Hampton

TBA at The Vanguard Brewpub & Distillery

Ring in the New Year with the high energy rock of the 1990s with Woah 90s Band at the Vanguard Brewpub and Distillery

From the Calendar: