Explore Olde Towne Portsmouth for a Fun Evening Out

A view of Portsmouth, Virginia on a sunny day, showing multiple buildings of different sizes.

If you want to stroll through three centuries of historic neighborhoods where you’ll find antique shops, delightful restaurants, and so much more, head to Olde Towne Portsmouth. It’s one of the country’s oldest seaports, and it’s just a quick drive from Waypoint Apartments. It also features the longest-running operational naval hospital and the first dry dock facility in the United States. Other highlights include:

Skipjack Nautical Wares

Make this shop your first stop in Old Towne Portsmouth. Skipjack Nautical Wares was created in 2003, just a few years after the owners became inspired by a sail and dive trip through the British Virgin Islands. The owners are passionate about living the coastal lifestyle. They decided to offer antiques, exceptional marine art, and their own line of nautical products. The shop spans 6,500 square feet, and the inventory is constantly changing. Items may include things such as table lamps, ship bells, and colorful paintings.

Legend Brewing Co.

Legend Brewing Co. offers the finest and most flavorful beers around. It’s one of the only craft breweries in the region to produce both ales and lagers, and you can find a wide selection of unpasteurized beers. The brews also feature two-row specialty barley malt, water, and specialty hops. Guests can enjoy their time inside or on the patio featuring scenic water views. The brews include Spring Pale Ale, Legend Tripel, and Hopfest.

Commodore Theatre

Listed on the National Register of Historic Places, the Commodore Theatre opened in 1945. It was widely known as a movie lover’s dream. Built in the art deco style, it features a 41-foot screen, THX and Dolby Digital Sound, and a full-service restaurant within the main auditorium. Stop by for a great meal or dinner and a movie.


Olde Towne Portsmouth is just one of the neighborhoods you can explore if you call our apartments in Hampton Roads home. If you want to find more old treasures, head to the Williamsburg Antique Mall, too. Please contact our leasing agents to arrange a tour where you can see the amenities at Waypoint Apartments firsthand.

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