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Olde Towne Scottish Walk

Olde Towne Portsmouth Olde Towne, Portsmouth, VA

 This annual event is modeled after Scotland's Hogmanay Festival, the walk is a day when townspeople honor their community and merchants, wishing them good luck and prosperity in the coming year. The Scottish Walk leads off from London and Washington streets in Olde Towne Portsmouth.

Free

Recurring

50th Annual Seawall Art Show

Olde Towne Portsmouth Olde Towne, Portsmouth, VA

Join us for the 50th Annual Seawall Art Show, featuring the works of more than 65 local and regional artists. Peruse paintings, sculptures, jewelry and more. Plus enjoy food and live entertainment in charming Olde Towne Portsmouth. Don’t miss it!

50th Annual Seawall Art Show

Olde Towne Portsmouth Olde Towne, Portsmouth, VA

Join us for the 50th Annual Seawall Art Show, featuring the works of more than 65 local and regional artists. Peruse paintings, sculptures, jewelry and more. Plus enjoy food and live entertainment in charming Olde Towne Portsmouth. Don’t miss it!

Shop Small Saturday in Olde Towne

Olde Towne Portsmouth Olde Towne, Portsmouth, VA

Skip those Black Friday crowds and come ENJOY Shop Small Saturday in Olde Towne! Get your holiday shopping started a bit earlier this year! Starting at 10 am, visit all of the beautifully decorated shops, listen to great live music, and treat yourself to a relaxing lunch in one of our 26 chef-owned restaurants! Come […]

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. In 2022, this special day of music and friendship takes place on Saturday December 10th, from 11 AM until 5 PM. You’ll find even more music in restaurants, bars, and churches after the festival […]

Free

Holiday Homes Tour

Olde Towne Portsmouth Olde Towne, Portsmouth, VA

Experience the spirit of olde world charm with festively decorated homes in the heart of Portsmouth’s Olde Towne Historic District during the Holiday Homes Tour from 1 to 6 p.m. on Saturday, December 10, 2022. Tickets are $15 for the self-guided walking tour. Upgrade to the Golden Ticket and add a tour of the Hill […]

Recurring

Candlelight Caroling with Father Christmas and Mary Veale

Olde Towne Portsmouth Olde Towne, Portsmouth, VA

Join Father Christmas and Mary Veale as they carol, impart a bit of history, and tell stories along a special route through Olde Towne Portsmouth. Caroling begins at the Christmas Tree outside the Children's Museum in Middle Street Mall and ends with a tour and refreshments at Historic Hill House, after which guests will be […]

Recurring

Restaurant Week

Olde Towne Portsmouth Olde Towne, Portsmouth, VA

Restaurant Week is a time for Portsmouth to show off its wide variety of gourmet specialties. Our local chefs are preparing menus that are guaranteed to leave you wanting more. Participating restaurants will offer special menus with options for two-course lunches and three-course dinners.

Recurring

Olde Towne Antique & Flea Market

Olde Towne Portsmouth Olde Towne, Portsmouth, VA

Visit the Olde Towne Antique & Flea Market on the first Saturday of each month, rain or shine, and enjoy the eclectic collection of unique and antique wares. With more than 70 vendors, you will discover a great selection of antique and flea market items of all types – priced to sell! Shop for estate […]