Experience the best of the best with this Top 8 list of things to do and see in Portsmouth.
Walk through history and see Olde Towne’s origins and it’s continued evolution.
Plan for your visit and explore Portsmouth with the Visitor Directory.
Bring the whole family out to the holiday celebrations in Portsmouth. In this article, learn more about special events and activities, shopping specials, musical events, events for adults only, and even what’s planned for New Year’s Eve.
This festive holiday event kicks off the season. The Holiday Tree Lighting includes Sugar Plum Fairies dancing, a message from Father Christmas, carols from the Olde Towne Arts & Music Children’s Chorus, and even a little snow! It all takes place on the Middle Street Mall at 5:30 p.m.
Olde Towne’s merchants come together to bring you a holiday experience like no other at the Olde Towne Holiday Open House & Crafters’ Market. November 19 from 4-8 p.m. All along High Street, there will be decorations, music, fairies, snow, hot cider, and shops open late to make your gift-shopping easy! Visit the Crafter’s Market on the Middle Street Mall first, enjoy the tree lighting festivities, and then venture out onto High Street to explore the shops and grab some dinner.
Peace & Grind Wellness, at 313 High Street, will be hosting a community shopping event with other local business from 10am-3pm and 5pm-10pm on November 27th. There will be doorbusters and other freebies available! Then, come back to Peace & Grind December 21-23 from 10am-8pm for a holiday-themed Winter Market. Arts, crafts, and gift wrapping services will be available as well! Decorate a gingerbread man or make your own DIY Christmas ornaments.
Every day is Shop Small in Portsmouth. While we love our Walmart, Lowes, Kroger Marketplace, and other big box stores, Portsmouth is really known for its small boutiques, antique, and specialty stores. These are the places where you often find the owners behind the counter and where families depend on you shopping local this year. The Olde Towne merchants have come together to make Shop Small Staurday a special event. Skip those Black Friday crowds and ENJOY Shop Small Saturday in Olde Towne Portsmouth! Look for the Olde Towne Business Association tent at the Portsmouth Welcome Center. The first 50 shoppers will get a swag bag. Mary Veale and the Colonials will provide strolling historic interpreters. We will have holiday music including a violinist. The KOMI Art Market will be set up with local artists on the corner of High & Court Streets. troll our brick sidewalks and visit our 16 beautifully decorated shops. Treat yourself to a relaxing lunch or dinner in one of our 26 chef-owned restaurants! Come join us in celebrating the places we love!
On Museum Shop Sunday, the local musuem shops will offer 25% off to members and 15% off to the general public. You can shop the Children’s Museum of Virginia Gift Shop, The Portsmouth Naval Shipyard Museum Gift Shop, and the Portsmouth Welcome Center’s Gift Shop to receive this special discount. Just a hint, if you shop small Saturday and stop by one of these gift shops, you can still get the discount.
Each year, Trinity Church provides a Children’s Christmas Shoppe in the fellowship hall. This a an opportunity for children ages 3-12 to shop for their familes and friends assisted by one of Triity’s Elves. All gifts are only $4 and are wrapped to keep the surprise a secret. While the parents are waiting, they can browse the Craft Tables where just the right gift might be found. The Children’s Christmas Shoppe is open Saturday, December 11th from 9 a.m. until 4 p.m. and on Sunday, December 12th from 12 p.m. – 4 p.m. (no gift wrapping on Sunday). Due to the ongoing COVID crisis, appointments are required on Saturday. Reserve your child’s time to shop online.
There will be a white Christmas on the Middle Street Mall outside the Children’s Museum of Virginia every Friday and Saturday starting November 26th, even if it isn’t freezing out. The whole family can enjoy Snow Wonders for free from 5:30-6:00 PM! Then, take the little ones to see Visits with Santa at the Winter Wonderland exhibit in the Portsmouth Art and Cultural Center! For only a few dollars per person, enjoy the Victorian Christmas displays of Winter Wonderland: The Coleman Collection every Wednesday-Sunday starting November 26th. The exhibit is open 9am-8pm Fridays and Saturdays, and 9am-4:30pm Wednesday, Thursday, and Sunday. Santa will only be available from 3-8pm Friday til Sunday, though, so plan accordingly.
Over at Monumental Methodist Church on Dinwiddie Street, the the Coleman Collection’s very special Nativity Scene is on display. The exhibit is open for the Olde Towne Open House on November 19th from 4 p.m. until 8 p.m. Regular viewing is on Saturdays from 11 a.m. until 5 p.m. and Sundays from 12:30 p.m. until 5 p.m. starting November 27th and closing on December 19th.
Inside the Children’s Museum of Virginia, don’t miss the special Holiday Planetarium Show called Santa’s Secret Star. The show airs Wednesday through Sunday at 10 a.m. and 2:15 p.m, with a special showing on Fridays and Saturdays at 5 p.m. In addition to the show, the Children’s Museum of Virignia offers a number of holiday themed workshops throughout the holiday season. Look for information on the website.
Mary Veale and the Colonials introduce new holiday characters over the holidays. Rabbi Atschul shares the customs and history of Hanukkah, the Jewish Festival of Lights. Father Christmas spreads merriment and good cheer while sharing the history and customs surrounding this important Christian observance . And Babu, which translates “ancestor”, discusses the symbols, principles, and culture of Kwanzaa. The Colonial Carolers and Colonial Kids will also be on hand to celebrate the season with song. The troupe of Colonials will take you on a Caroling Tour of Olde Towne too. Join Father Christmas and the Colonial Carolers and tour the historic Olde Towne neighborhood. Contact Mary Veale and the Colonials for tour times, tickets, and private engagements.
What embodies the holiday spirit more than music? Enjoy jazz, blues, swing, and more holiday music! Jazz guitarist Don Comer will perform live in the Garden House at Anderson Wright Rooms and Gardens on High Street November 19th at 6pm, as part of the Olde Towne Holiday Open House. Also that same night, the Tidewater Winds Ensemble Holiday Concert will be ongoing at Trinity Episcopal Church on High Street from 7:30pm.
On December 3rd at 7:30pm, the Tidewater Concert Band performs holiday music at Churchland High School for the 50th year! Tickets are $25 per person. The concert is sponsored by Portsmouth Community Concerts, and organization dedicated to music and music education since 1938. Tickets can be purchased in advance or at the door.
Last but not least, Portsmouth’s signature holiday event is the Olde Towne Holiday Music Festival taking palce from 11 a.m to 5 p.m. on and around High Street on December 11th. The event features performances by the Rhondels, Southsie Community Concert Band, Dixieland Strollers, Colonial Carolers, Michael Clark Band, Better by Tuesday, the Doorway Singers, Tidewater Concert Band, and many more. You’ll find entertainmern on the streets, in the shops and restaurants, and even in the historic churches. There’s a kids area and marshmellow roasting stations on the corners.
The Carrie B Showboat takes its last adventure of the season with a Sophisticated Cruise featuring a tasting of seven whiskies, cigars for those who smoke them, jazz with the Portsmouth Jazz Experience, and catering by Roger Brown’s. If you’re a whiskey lover, you don’t want to miss this opportunity. Tastings include the MacAllan Rare Cask, Elijah Craig Naked Malt, Pendelton, Bushmills, Larceny and more. Boarding begins at 5 and the ship sails at 5:30.
Enjoy the traditional St. Nicholas Day tapping of the Samichlaus (Santa Claus) keg at the Bier Garden in Olde Towne Portsmouth on December 6th at 5pm. This strong beer featuring holiday flavors and known as doppelbock style comes directly from Schloss Eggenberg brewery in Austria. For a non-alcoholic holiday treat, visit Hill House Museum on December 11th from 3-4:30 PM and enjoy an array of desserts, scones, sandwiches, and Hill House’s own tea blend. Admission is $35 per person, with all proceeds going toward restoration of the museum.
In addition to the German and English holiday traditions, Olde Towne will feature a Scottish (walk) tradition, a Hogmanay Festival procession through Olde Towne, on December 31st from 4-6pm. Meet friends and neighbors at Monumental United Methodist Church, on the corner of Queen St. and Washington St., and walk through Olde Town to High Street Landing, where a flag ceremony will honor George Washington’s raising of the first US flag. The Olde Towne Scottish Walk continues the tradition of wishing the community good luck and prosperity in the coming year.
Countdown to Noon at the Children’s Museum of Virginia starts at 11 a.m. and while the ball drops at noon, the kids are entertained with projects and activities until 2.