1. Events
  2. Olde Towne Portsmouth
Today

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 […]

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.

St. Patrick’s Day Weekend in Portsmouth

Olde Towne Portsmouth Olde Towne, Portsmouth, VA

Check out all the things to do St. Patrick's Day Weekend in Portsmouth.  Please celebrate responsibly and have a great time! FRIDAY MARCH 17 Momac Brewing kicks off the weekend with a special brew, food trucks, and Irish music by Siren City and Sean Heely and Friends.  The party goes from 12 - 9 Friday. […]

Virginia Historic Garden Week Olde Towne Tour

Olde Towne Portsmouth Olde Towne, Portsmouth, VA

Discover Virginia’s Historic Seaport located in the heart of Hampton Roads. Olde Towne Portsmouth is rich in maritime history due to its prime location on the Elizabeth River, and features a significant collection of 19th century architecture. Visitors will be welcomed to five locations, which include private homes and secluded gardens. Most are showcased this […]

$35

Witches and Worlocks Olde Towne Pub Crawl – Portsmouth Humane Society

Olde Towne Portsmouth Olde Towne, Portsmouth, VA

Raise a glass – and lifesaving funds for the animals – at Portsmouth Humane’s Annual Pub Crawl! Join us on Saturday, November 4th from 5 pm to 9 pm in Olde Towne Portsmouth. Conjure your finest witchy (or wizardy) garb, and crawl down High Street. Search for clues to solve the mystery – Where has […]

$30.00

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 on Saturday December 9th, from 11 AM until 3 PM. You’ll find even more music in restaurants, bars, and churches after the festival officially ends. […]

Free

Olde Towne Scottish Walk

Olde Towne Portsmouth Olde Towne, Portsmouth, VA

The annual Portsmouth tradition is 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. Gather at 4 pm at the corner of Queen and Washington Streets. The […]

Free

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 […]