Portsmouth Virginia Entertainment & Events
Special Events
Olde Towne Holiday Music Festival
Located Along High Street
757-393-9933
Portsmouth's very own signature holiday event, this event takes place in early December and includes musical performances by the best local and regional music groups, choirs, and musicians. This event also features bonfires, street entertainers, and children's activities. more...Arts & Antiques Open House
622 High Street • Portsmouth, VA 23704
Located in Olde Towne on High Street
757-398-0990
An annual event that features art, antique, speciality shops, and restaurants kicking off the holiday season each November. Opening shows and receptions are featured at local art galleries. This event also includes free horse-drawn wagon rides, complimentary refreshments at many of the shops, and an antique car show.100 Miles of Lights
Located at Various Venues and Cities
Millions of lights and hundreds of events will entertain visitors to Central and Southeast Virginia this holiday season during this spectacular event that lasts for almost a month and a half and features activities in Richmond, Williamsburg, Newport News, Hampton, Norfolk, Portsmouth, and Virginia Beach. Features such as drive-through and walk-through light shows, lighted boat parades, festivals, parades, living history re-enactments, and caroling will be featured. more...Grand Illumination
Located in Olde Towne
757-393-5111
Skylines stretched nearly 20 miles light up during this holiday event that includes a holiday parade, complete with festive and lighted floats, marching bands, giant balloons, decorated vehicles, dancers, and, Santa Claus.
Cinema
Commodore Theatre
421 High Street • Portsmouth, VA 23704
757-393-6962
A luxuriously restored 1945 Art Deco style motion picture theater that presents first-run films on a 41-foot cinema screen, complete with THX and Dolby Digital surround sound. A restaurant is also on site which serves light American fare, such as the best in sandwiches, desserts, and pizzas. more...
Concerts & Performances
Willet Hall
3701 Willett Drive • Portsmouth, VA 23707
757-393-5460
A 2,000 seat performance arts theater and entertainment facility that has outstanding acoustics and offers concerts, guest speakers, theater, musicals, dance performances, broadway shows, children's shows, and other entertainment events throughout the year.
Art Exhibits
Seawall Art Show
Located at High Street Landing
757-393-8983
An outdoor juried art show that features the work of nearly 100 artists from New York to Florida with items available including oils, acrylics, watercolors, pastels, photography, pottery, stained glass, handmade baskets, and handcrafted jewelry. Continuous entertainment is provided throughout this two day event. more...
Flea Markets
Antiques to Flea Market
441 Middle Street • Portsmouth, VA 23704
Located at Middle Street Garage
757-339-1876
Held on the first Saturday of each month from 10 a.m. to 2 p.m., this large flea market features a huge mix of antiques, collectibles, books, art, crafts, furniture, and much more.
Festivals & Fairs
Taste of Monticello Wine Trail
16 Crawford Circle • Portsmouth, VA 23704
nTelos Wireless Pavilion
Brings together some of the best vineyards in Virginia. Sample over 90 wines from a variety of vineyards. more...Umoja Festival
901 Crawford Street • Portsmouth, VA 23704
Located at the NTELOS Pavilion at Harbor Center
757-393-8481
This African-American cultural celebration lasts for three days and includes national recording artists, local entertainers, an African marketplace, children's activities, a community forum, heritage tours, Afrocentric foods, educational exhibits, living history presentations, African dancers, heritage trolley tours, and a holiday house race. more...Gosport Arts Festival
Located in Olde Towne
757-446-2361
Established over 30-years ago, this art show has become synonymous with the area’s celebration of spring and the show features a wide variety of works of art by local, regional, national, and international artists. The show takes place on Mother's Day Weekend. more...Umoja Festival [Friday, May. 24, 2013]
Ntelos Pavilion
757-393-8804
Umoja means unity. Celebrate at this African-American culture and heritage festival promoting cultural diversity and unity. The festival will feature live music, a heritage tour, kids activities, food, and more. more...
Sporting Events
Eastern Amateur Golf Tournament
1 Ace Parker Drive • Portsmouth, VA 23701
Located at Elizabeth Manor Golf & Country Club
757-488-6605
An exciting annual golf tournament that attracts the top 150 amateur golfers in the United States and abroad. Participants compete to win during this classic, five-day tournament. more...Portsmouth Cavaliers
2301 Oregon Avenue • Portsmouth, VA 23701
757-642-0147
The Portsmouth Cavaliers professional basketball team will represent the City of Portsmouth, and the Commonwealth of Virginia. The Cavaliers will be playing in American Basketball Association (ABA) this fall competing against teams across the East Coast.Portsmouth Invitational Tournament
4301 Cedar Lane • Portsmouth, VA 23703
Located at Churchland High School
757-393-5327
Recognized by NBA managers and scouts as the premier showcase for hot prospects, this four day event consists of 24 of the country's top college senior basketball players competing in the nation’s oldest amateur tournament for the opportunity to play professional basketball. more...
Tours
Old Towne Candlelight Home Tour
Located in Downtown Portsmouth
Located in historic Portsmouth, Virginia, this annual self-guided walking tour is one of the signature events of the holiday season in Hampton Roads.Olde Towne Ghostwalk
Begins in Cemetery of Trinity Episcopal Church
757-397-7261
Based on the famous Jack-the-Ripper Walks in London, this guided walking tour takes visitors past the haunted houses and mysterious mansions of historic Olde Towne Portsmouth where costumed actors or actresses re-tell the legends of ghostly visitations. more...
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