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Olde Towne Holiday Market & Tree Lighting

Middle Street Mall 221 High Street, Portsmouth

Enjoy a hometown holiday tree lighting complete with decorations, music, the Snow Queen, Sugar Plum Fairy, Cindy Loo Hoo, the Grinch, Father Christmas, and even a little snow! Additionally, the […]

Shop Small Business Saturday

High Street Corridor 206 High Street, Portsmouth, VA

Celebrate local business and Shop Small this Saturday.  Portsmouth is known for it's unique shops and restaurants, mom and pops, and owner operated.  Their livlihood depends on you.  Not everything […]

Museum Store Sunday

Score discounts at all Portsmouth museum stores during Museum Store Sunday. Thank you for supporting your local museums this holiday season! Discounts available at the Children’s Museum, Portsmouth Art & […]

Recurring

Painted Glass Ornaments

Portsmouth Art & Cultural Center Annex 420 High Street, Portsmouth, VA

Portsmouth Art & Cultural Center Art Annex Saturdays NOV 25 and DEC 2 from 3:30 – 7:30 p.m. Winter Wonderland ticketholders can partake in an activity where they paint on […]

The Gents Live Holiday Show at Sound Bar

Sound Bar at Rivers Casino 3630 Victory Blvd., Portsmouth, VA

Join us at The Sound Bar for Holiday with the Gents  on Sunday, Dec 3, from 4PM - 7PM. Enjoy live performances by Eddie, Lee, and Dr. Joel. Classical Holiday music sung like only they can.  Don't miss the holiday magic!

Winter Concert at I.C. Norcom

I.C. Norcom High School Auditorium 1801 London Blvd, Portsmouth, VA

Enjoy a holiday performance by the I.C. Norcom High School artists.  Members of the chorus, band, orchestra, and drama club come together for a one night, over-the-top performance.  You don't want to miss it.

Portsmouth Community Concerts presents The Collingsworth Family “A True Family Christmas”

I.C. Norcom High School Auditorium 1801 London Blvd, Portsmouth, VA

The Portsmouth Community Concerts presents its 85th season. Tickets available for individual shows for $25 each (adults) or get your tickets for the entire season for only $85 A Southern Gospel/Inspirational family known for staying together, praying together, and singing together will bring a certain degree of excitement, spiritual anointing, and musical excellence to the […]

$25.00

Olde Towne Holiday Music Festival

Olde Towne Portsmouth Olde Towne, Portsmouth, VA

The Olde Towne Holiday Music Festival began in 1998 and has become the signature holiday event for the City of Portsmouth. This special day of music and friendship takes place […]

Free

Holiday Painted Stones

Portsmouth Art & Cultural Center Annex 420 High Street, Portsmouth, VA

Portsmouth Art & Cultural Center Art Annex Saturday DEC 9 from 3:30 – 7:30 p.m. Folks of all ages love painting stones whether they know it or not, so as part of visitors’ tickets to Winter Wonderland, we will be offering this as a holiday activity make-n-take.  Adults and children can choose from three different […]

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Santa Claus Shuffle 5k and 1-mile Fun Run

Atlantic Union Bank Pavilion 16 Crawford Cir, Portsmouth, VA

Sponsored by Tidewater Youth Services Foundation. Put on your antlers, elf hat, or full Santa regalia and take a run down the Portsmouth Seawall for a good cause.  Gather at […]

$25.00
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Children’s Christmas Shoppe

Trinity Episcopal Church 500 Court Street, Portsmouth, VA

Trinity Episcopal’s Christmas Shoppe will be celebrating it’s 30th year on Saturday, December 14.  The shoppe will be open from 9 am to 3:30 p.m. by appointment.  Children between the ages of 3 and 12 years may sign up on our website beginning November 11th. Each child with the help of an elf may purchase […]

Santa Claus Shuffle After Party

Post Secondary Brewing Company 739 High Street, Portsmouth, VA

After the race, join your fellow runners, walkers, spectators, and anyone else who would like to be there for an after party.  Food truck, drink specials, and more.