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Olde Towne Holiday Music Festival

High Street Corridor 206 High Street, Portsmouth, VA

Live entertainment, strolling carolers, roving costumed characters, marshmallow roasting stations, children’s activities and more during this city holiday tradition.

Free

Olde Towne Market Day

High Street Corridor 206 High Street, Portsmouth, VA

Olde Towne Market Day is actually 7 markets rolled into one!  Spend the day on High Street and enjoy the shops and restaurants as well as all of these wonderful outdoor markets:   Portsmouth Olde Towne Farmers Market 9 a.m. - 2 p.m. High and Court     Get Colorful and Paint Your Hearts Out […]

Recurring

51st Annual Seawall Art Show

High Street Corridor 206 High Street, Portsmouth, VA

Saturday, August 26 and Sunday August 27, The 51st Annual Seawall Art Show returns to High Street. If you want to find that one-of-a-kind gift for someone special or a signature piece for yourself, then come to our show, located on in Portsmouth, Virginia's historic downtown. You will find a little of everything from wood […]

Olde Towne Portsmouth Business Expo

High Street Corridor 206 High Street, Portsmouth, VA

Sponsored by the Olde Towne Business Association. Enjoy a fun day of bargains, local musicians, strolling historical interpreters, and prize give-aways along High Street.  The OTBA tent is at the Portsmouth Welcome Center where you'll find cool Olde Towne merchandise as well as prize drawings every hour.  Look for special sales and pop ups along […]

Fish Bowl Classic Parade Cancelled

High Street Corridor 206 High Street, Portsmouth, VA

Cancelled Due to Inclement Weather For more than half a century, this event has been sponsored by Arabia Temple #12 and is followed by the Fish Bowl Classic football game, held at I.C. Norcom at 2 pm. For more information, please call (757) 761-4455. The parade begins at I.C. Norcom and travels down High Street […]

I C Norcom Homecoming Parade

High Street Corridor 206 High Street, Portsmouth, VA

The parade kicks off at IC Norcom and travels down High Street, through Olde Towne to Water Street.

Shop Small Business Saturday

High Street Corridor 206 High Street, Portsmouth, VA

Celebrate local business and Shop Small this Saturday.  Portsmouth is known for it's unique shops and restaurants, mom and pops, and owner operated.  Their livlihood depends on you.  Not everything has to come from big box or online store.  Support your neighbors. The day begins at 10 AM.  Be one of the first and visit […]

St. Patrick’s Day Pub Parties and Bawdy Show

High Street Corridor 206 High Street, Portsmouth, VA

3:00 - Take in the show at Post Seconday Brewing as History Alive presents Irish Bawdy Tunes and Sea Shanties.  It's an hour long performance of bawdy tunes for adults only.  Get primed for the pub crawl that follows.  After the show, the troupe of characters will escort you to the participating pubs.  Post Secondary […]

A Post Such As Portsmouth-1781

High Street Corridor 206 High Street, Portsmouth, VA

A Post Such as Portsmouth is an immersive, interactive, educational, child-friendly, annual spring event commemorating the 1781 British occupation of Portsmouth by the turncoat Benedict Arnold himself.  On Saturday, April 13th, Olde Towne Portsmouth will be brimming with reenactors, interpreters, and the like, as Youth Virginia Regiment hosts this one-of-kind event.  Even residents and shop […]

Free

Celebrate the District – The Portsmouth Cultural Arts District

High Street Corridor 206 High Street, Portsmouth, VA

Music, food trucks, make and take programs, working artists, break dancers, skateboarding demos, and a bunch of new murals.  A shuttle will run from 12 pm - 4 pm and will connect all the museums and event locations with parking and the ferry. This event is actually made of up multiple arts related events including: […]

Recurring

Steeple to Steeple Historic Tour

High Street Corridor 206 High Street, Portsmouth, VA

A tour of eight historic churches and one synagogue in Olde Towne Portsmouth. Explore the architecture , stained glass, and memorabilia of these historic structures. You'll hear stories of the Yellow Fever epidemic, the Underground Railroad, the Irish immigrants who built a masterpiece, the Jewish community who began settling in Portsmouth as early as 1916, […]

$22.00
Recurring

Annual Memorial Day Parade

High Street Corridor 206 High Street, Portsmouth, VA

What is known to be one of the longest running Memorial Day parades in the country, the City of Portsmouth’s Memorial Day Parade began in 1884. Since that time, Portsmouth has recognized and honored the sacrifices of the brave men and women in the United States Armed Forces each year during the parade. Enjoy floats, […]