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Breakfast with Santa in Cradock

Church of the Holy Angels 34 Afton Parkway, Portsmouth

The Cradock Lion's Club presents Breakfast with Santa.  Bring the kids out for a free breakfast hosted by the jolly old elf himself.  It's a great opportunity for photos too. […]

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Children’s Christmas Shoppe

Trinity Episcopal Church 500 Court Street, Portsmouth

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 […]

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Brunch With Santa at Cure Coffeehouse

Cure Coffeehouse 725 High Street, Portsmouth

Stop by Cure Coffeehouse and let Santa know what's on your wishlist.  Have a coffee and some breakfast too.  Kick off the Olde Towne Holiday Music Festival on a full […]

Second Saturdays: Winter Celebration

Children's Museum of Virginia 221 High Street, Portsmouth

Join Andalo for winter carnival games and face painting, and learn how to make your own snow!

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Christmas Market at MoMac Brewing

Momac Brewing Company 3228 Academy Ave, Portsmouth

Join us for a Christmas Market! We will have a coffee truck with lots of yummy holiday treats! Get ready for the holidays by shopping local from over 30 different […]

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Olde Towne Holiday Music Festival

Olde Towne Portsmouth Olde Towne, Portsmouth

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

Christ, Cars, and Christmas Festival

Portsmouth Christian Church 3150 Detroit Street, Portsmouth

Portsmouth Christian Church presents Christ, Cars and Christmas Festival. 3150 Detroit Street, Portsmouth, Va 23707 EVENT DETAILS: CLASSIC, MODERN, AND MUSCLE CAR SHOW: CAR SHOW REGISTRATION- 11AM-1PM CAR SHOW 1PM- […]

The Christmas Project Band Live at Roger Brown’s

Roger Browns Restaurant and Sports Bar 316 High Street, Portsmouth

Join us as we partake in the Olde Towne Holiday Music Festival with the seasonal sounds of The Christmas Project Band. There will be music and dancing all down High […]

Handbells, Choir, and Carols at Monumental

Monumental United Methodist Church 450 Dinwiddie St, Portsmouth

As part of the Olde Towne Holiday Music Festival, the church offers a special performance to celebrate Christmas.  Free and open to all.

Holiday Tea at the Hill House Museum

The Hill House Museum 221 North Street, Portsmouth

NEW LOCATION!  Due to an issue with the furnace, the Tea has been moved to historic Cambridge Hall located on the corner of London and Washington Streets.  Only a few tickets remain. Celebrate an annual holiday event at the Hill House Museum.  Enjoy a wonderful assortment of desserts, scones, and sandwiches as you savor a […]

$35.00

Holiday Painted Stones

Portsmouth Art & Cultural Center Annex 420 High Street, Portsmouth

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 […]