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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 […]

Free

Shop the Block High Street Festival

High Street Corridor 206 High Street, Portsmouth, VA

The annual Shop the Block High Street Festival is an interactive one-day community celebration of creative commerce spotlighting storefront activations, artistic displays, family activities, sensational food and entertainment experiences within the […]

Olde Towne Holiday Lights

High Street Corridor 206 High Street, Portsmouth, VA

From a snowy tree lighting to the arrival of Santa Claus, join us for a progressive lighting of the city. DOWNLOAD THE FULL SCHEDULE OF EVENTS HERE! Festivities begin at […]

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 livelihood depends on you.  Not everything […]

Portsmouth Rotary Club’s Olde Towne Chocolate Crawl

High Street Corridor 206 High Street, Portsmouth, VA

Olde Towne restaurants participating in our inaugural Chocolate Crawl! Grab your valentine (or galentine) and come out for a tasty evening exploring chocolate-inspired food and drink pairings along High Street. Tickets […]

$25.00

Recurring

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, March 22nd & 23rd, 2025,  Olde Towne Portsmouth will be brimming with reenactors, interpreters, and the like, as Youth Virginia Regiment hosts this one-of-kind event.  Even […]

Free

Recurring

Steeple to Steeple Historic Tour

High Street Corridor 206 High Street, Portsmouth, VA

A tour of seven 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, […]

$25.00

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, […]

Portsmouth Pride Pub Crawl

High Street Corridor 206 High Street, Portsmouth, VA

This is a free pub crawl to support Portsmouth Pride.  Join us on Saturday evening for drink specials and maybe even a few special drinks from these Olde Towne establishments. Post Secondary Brewing Cure The Bier Garden Roger Browns Charm and Manners Fish & Slips Longboards ELG Sweet Boutique Thyme on the River Guads Olde […]

Recurring

Portsmouth Puns and Plunder Scavenger Hunt

High Street Corridor 206 High Street, Portsmouth, VA

About this Portsmouth Virginia Scavenger Hunt Ahoy, mateys! Are you ready to set sail on a journey filled with history and mystery? Join us for the Portsmouth, Virginia, scavenger hunt […]

$12.99