The Coleman Collection's Sleeping Santa display at Winter Wonderland
Olde Towne Antiques to Flea Market every first Saturday, Portsmouth Virginia
High Street decorated for the winter holidays, Olde Towne Portsmouth Virginia
Snow Wonders snow, music, and light display at the Children's Museum of Virginia

December 2017 · Portsmouth, Virginia Events and Activities


December 31

Winter Wonderland: The Coleman Collection

Location: Portsmouth Art & Cultural Center

Celebrate the season with Winter Wonderland: The Coleman Collection, a holiday classic for generations of Hampton Roads visitors and residents.  Animated displays feature Victorian skaters and carolers, enchanted forest of bears, deer and other fauna along with Santa’s workshop, candy store and bakery.  These holiday displays delight visitors of all ages.


December 2

10 am – 2pm

Olde Towne Antiques to Flea Market

Location: Middle Street Garage

Great finds of all kinds. With more than 70 dealers and vendors exhibiting, you will enjoy hunting through this eclectic collection of unique and antique wares. Discover a great selection of antique and estate furniture, architectural antiques, china, silverware, art and prints, sporting gear, musical instruments, books and ephemera, handmade crafts and toys, as well as decorative accessories and flea market items of all types and one of a kind items priced to sell. For more information please call 757-405-3500.


December 9

10 am

Children’s Christmas Parade

Location: High Street – Olde Towne

Join us for the Children’s Christmas Parade and watch as we bring a twinkle to the eyes of the young and old alike. The parade will start at Green and High Streets and travel to Water Street. For more information or to register your holiday entry please call 757-393-8481


December 9

Noon – 6 pm

20th Annual Olde Towne Holiday Music Festival

Location: High Street Corridor (Historic Olde Towne)

Join the Olde Towne businesses and museums for holiday music and carols. This festival has become one of Portsmouth’s signature holiday season events. It is a musical tribute to the spirit of the Holiday Season, enlivening the historic High Street corridor with performances, children’s activities, re-enactors in period attire and strolling characters. For more information call the Department of Marketing, Entertainment and Tourism at 757-393-5143.


December 19

6 pm

Family Movie Night

Location: Churchland Library

Enjoy the latest series of programming at Churchland with our monthly movie night. Movie will be shown on the big screen. Bring a friend and munch on some popcorn! For more information please call 757-686-2538.


December 31

11 am – 2 pm

Noon Year’s Eve Bash: Countdown to Noon

Location: Portsmouth Art & Cultural Center

Bring in the New Year before bedtime by celebrating with a Countdown to Noon with a glittery ball drop and toast. Face painting, magic and balloon-making will take place along with a photo booth and refreshments. After “Noon Year” arrives, kids can create their own fireworks on a carpet of giant bubble wrap. For more information please call 757-393-8543 or visit


December 31

3:30 pm

Olde Towne Scottish Walk

Location: Queen and Washington Streets continue to High Street Landing

Modeled after Scotland’s Hogmanay Festival, the walk is a day when townspeople honor their community and merchants, wishing good luck and prosperity in the coming year. Join the procession of families, friends and visitors led by bagpipe-and-drums. Begin at the corner of Queen and Washington Streets and continue to High Street Landing for a flag ceremony that honors George Washington’s raising of the first flag, the Grand Union. For more information please call 757-650-3052.

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