Portsmouth Virginia Signature Events

Shaggin’ on High

The 3rd Annual Shaggin’ On High takes place July 6 and is a tribute to Portsmouth’s Bill Deal and Beach Music. This year’s event features the Carolina Breakers. Come on down to Olde Towne, Portsmouth for good old-fashioned fun. Shaggin’ On High is free and open to the public. Bring your lawn chairs and enjoy listening and dancing to great music. Beverages will be available for purchase. For more information please call 757-393-5111 or visit https://oldetowneportsmouth.com/events/shaggin-on-high/

Portsmouth Invitational Tournament: April

Each year for 63 years the P.I.T has invited 64 of the best college basketball players (seniors) from across the nation to participate in a four-day, twelve game tournament in front of representatives from every NBA team.  The tournament drew the attention of NBA Scouts and General Managers in the 1970s when players like Rick Barry, Earl “The Pearl” Monroe, Dave Cowens, John Lucas and Bobby Cremins came to Portsmouth to play.  Soon the word spread and approximately 200 Scouts, General Managers and Representatives of all 30 NBA teams began to come to see players like John Stockton, Dennis Rodman, Tim Hardaway, Scottie Pippen, and others.  Today scouts from numerous international leagues have joined in on the annual April pilgrimage to Portsmouth.  Over the years the P.I.T. has been a showcase for five of the 50 greatest players in NBA History (Rick Barry, Earl ‘The Pearl” Monroe, Dave Cowens, John Stockton, Scottie Pippen) and for many others who have gone on to NBA stardom including 2015 NBA All-Star Jimmy Butler.


Umoja Festival: Memorial Day Weekend

Friday thru Sunday: In 1991, the City Council of Portsmouth, Virginia affirmed its commitment to understanding cultural diversity. It was most appropriate that the City of Portsmouth selected the Kiswahili word UMOJA as the name of its African-American Festival. Umoja, a Kiswahili word meaning unity, is the first principal of Kwanzaa, an African-American cultural holiday celebrated from December 26th through January 1st. This principal emulates unity in the family, community, and nation.


Elizabeth River Run: Memorial Day Weekend

Saturday: Started in 1979 by Jerry Bocrie, this Tidewater Striders Club race has always been a runners’ favorite. ERR will be held on the exciting and scenic course in Portsmouth, Virginia. With magnificent views of the Elizabeth River, participants will traverse through Olde Towne with its towering monuments, museums, historical homes, and the Portsmouth sea wall. Following the race will be a post-race celebration at the spectacular Ntelos Pavilion.


Memorial Day Parade

A Portsmouth tradition since 1884. Annually, the Memorial Day Parade salutes the service and sacrifices of the men and women of the United States Armed Forces and celebrates Portsmouth’s proud military heritage. This year’s parade will include floats, marching band units, armed forces units, lots of excitement and much more.

For more information call the Department of Marketing, Entertainment, and Tourism at 757-393-5143.


Seawall Music Festival & Fireworks

First Friday and Saturday in June: Live music performances along the Portsmouth waterfront. Saturday events closed with one of the largest fireworks displays on the East Coast.


Cock Island Race: June

Since 1988, called one of the “Best Sailing Events on the East Coast” by landlubbers and sailors alike, this waterfront sailing classic features Friday and Saturday night live entertainment. Saturday is Race Day on the Elizabeth River.


Stars & Stripes Forever Concert & Fireworks

July 4th weekend: PortSide Park/Elizabeth River


July Jazz Concert

Free two-day Jazz event featuring local, regional, and national favorites.


Seawall Art Show: August

Last weekend before Labor Day: With more than 30 years experience showcasing juried fine arts and fine crafts on the Portsmouth waterfront, the Seawall Art Show draws large crowds of art buyers to this prestigious event. With the assistance of the Portsmouth Museum and Fine Arts Commission, it is an all-volunteer run show. Show proceeds always go to support the arts in Portsmouth.


Coast Guard City Celebration

In December of 2010, the City of Portsmouth was designated a Coast Guard City. The Coast Guard selected Portsmouth due to the City’s nearly 200 years of support of the Coast Guard community. The City of Portsmouth celebrates this grand distinction each year with a community celebration.


Olde Towne Safe Trick-Or-Treat

Saturday before Halloween: For children up to age 12. Located on the seven historic blocks of High Street corridor between Effingham Street and Water Street.  Sponsored by the Portsmouth Police Department, Portsmouth Sheriff Office, the Portsmouth Fire Department, and the Olde Towne Business Association. For more information please call. (757) 405-3500.


Grand Illumination Parade: Late November

Come see the kickoff to Holiday’s in the City, on the streets of downtown Norfolk. It beings with the illumination of the downtown Norfolk and Olde Towne Portsmouth skylines followed by Hampton Roads most cherished event, the Grand Illumination Parade. The themed parade will travel down Main Street to Granby Street then travel north to Freemason Street crossing over to Boush Street and around to Waterside Drive. Festive Floats, marching bands, giant balloons, dancers and Santa himself will delight spectators as they bring your favorite storybook characters to life.

For more information please call 757-623-1757.


Winter Wonderland

Opens Friday after Thanksgiving Celebrate the season with Winter Wonderland, a holiday classic for generations of Hampton Roads visitors and residents. Animated displays from the Coleman Collection feature Victorian skaters and carolers, enchanted forest of bears, deer and other fauna along with Santa’s workshop, candy store, and bakery. The holiday displays delight visitors of all ages.


Olde Towne Holiday Music Festival

Launched in 1998, this festival has become one of Portsmouth’s signature holiday season events. It is a musical tribute to the spirit of the Holiday Season, enlivening the historic High Street corridor with performances, children’s activities, re-enactors in period attire and strolling characters.

For more information the Department of Marketing, Entertainment, and Tourism at 757-393-5143.


Olde Towne Scottish Walk: December 31st

The Olde Towne Scottish Walk is modeled after Scotland’s Hogmanay Festival, a day when townspeople honor their community and merchant’s, wishing all the best luck and prosperity in the coming year. A procession of local family, friends, and visitors will be led by bagpipe-and-drum music down Queen and Washington Streets to High Street Landing for a flag raising ceremony that honors George Washington’s raising of the first flag, The Grand Union.

For more information please contact Susan Heeley 757-650-3052.


Children’s Museum of Virginia
221 High St. | 757-393-5258

Portsmouth Art & Cultural Center
400 High Street 757-393-8543

Portsmouth Community Colored Library Museum
904 Elm Avenue | 757-393-8983 ext. 20

Hoffler Creek Wildlife Preserve
4510 Twin Pines Rd. | 757-686-8684

Paradise Creek Nature Park
1141 Victory Blvd. | 757-399-7487

Atlantic Union Bank Pavilion
16 Crawford Cir. | 757-393-8181

Bide-A-Wee Golf Course
1 Bide-A-Wee Dr. | 757-393-8600

Portsmouth Naval Shipyard Museum
2 High Street | 757-393-8591

Lightship Portsmouth Museum
2 London St | 757-393-8591 P

Portsmouth Public Library
601 Court St. | 757-393-8501

Copyright © 2019
City of Portsmouth

801 Crawford Street
Portsmouth, VA 23704

PortsVaEvents.com is official Portsmouth Virginia calendar of events and activities. Owned and operated by the City of Portsmouth, Virginia for the posting of cultural events and activities hosted by, produced by, or in a local and regional partnership with the City of Portsmouth Virginia.