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Destination Portsmouth, Va.

This popular snowbird destination combines the best of Southern charm with history, culture and cruiser-friendly conveniences

This popular snowbird destination combines the best of Southern charm with history, culture and cruiser-friendly conveniences

When the fall migration of southbound snowbirds approaches its peak in October, the procession of boats cruising past Intracoastal Waterway Mile Zero off Portsmouth, Va., appears never to end.


Situated on the western shore of the Elizabeth River, 10 miles from the entrance to Hampton Roads, Portsmouth lies directly across from the bustling city of Norfolk. However, the two couldn’t be more different. Whereas Norfolk hums with urban zest, Portsmouth prides itself on its far more laid-back and friendly Southern ambiance. That’s why so many ICW cruisers en route to warmer climes take the time to tarry here and enjoy the museums, shops and fine restaurants.

Read the other stories in this package: Destination – Lightship Portsmouth   Destination – Portsmouth, Va. If you decide to go

“Portsmouth is really boater-friendly, and there’s so much for them to do, considering the attractions and events,” says Caroline Penney, manager of the Portsmouth Visitors Center at North Landing in the heart of the Olde Towne historic district, a compact residential area radiating inland from the waterfront with historic homes in Federal, Greek Revival, Classical Renaissance, Gothic and Romanesque architectural styles. “We like to think of the city as a quaint historic seaport, and we go out of our way to make boaters feel welcome.”

One way the city accomplishes this objective is by providing a cart at the visitor’s center that cruisers can use on the mile-long walk to the Food Lion, the nearest supermarket for provisioning. (Taxis also are available.) There’s a book trade library at the visitor’s center, as well as a loose-leaf folder containing restaurant menus. Hungry crews can check out the fare and prices before walking through the door. The spotless restrooms are open until midnight during the summer.

That Portsmouth is a popular destination becomes clear in October, when the two largest marinas in the heart of downtown go into full swing to accommodate snowbirds. “We get roughly 2,800 transients every year,” says Gordon Shelton, owner of Tidewater Yacht Agency. “In October alone we get more than 800. They come because the people in Portsmouth are friendly, it’s relaxing, and you can get pretty much all you need here.”

Portsmouth is the sister city to Portsmouth, England, and there’s evidence of that relationship all around. In front of the visitor’s center is an old-style English telephone booth, donated by thoughtful city officials of the Portsmouth across the Atlantic. The phone even works. High Street was named for the main commercial drag in Portsmouth, England and, appropriately enough, it runs parallel to King and Queen streets.

The history of Portsmouth dates back to 1607, when Capt. John Smith explored the Elizabeth River while he charted the lands near Jamestown. Settlement began in the mid-1600s, and throughout the 1700s a village grew into a thriving port. By 1793 there were 300 residences housing around 1,700 people. By 1806 the population had almost doubled.

The Navy — first British, then American — has long been a major presence in Portsmouth. The Gosport Shipyard was founded in 1767, and the ever-expanding facilities made Portsmouth a major military shipbuilding center. In 1827 the Navy built its first naval hospital at present-day Hospital Point — it’s still in operation as the Naval Medical Center — and in 1833 it built the first dry-dock in North America, also still in use.

During times of war, the shipyard — now known as the Norfolk Naval Shipyard and still the largest and oldest in the United States — was a prime target. It was burned three times. The yard was under Confederate control throughout much of the Civil War, and the frigate USS Merrimac was converted to the ironclad CSS Virginia there. The famous battle between the Virginia and the Monitor occurred in Hampton Harbor in 1862, setting the stage for the advent of modern battleships.

In addition to the Virginia, other important naval vessels built at the shipyard include the USS Raleigh, the first cruiser built in a federal yard. The USS Texas, launched in 1892, was the Navy’s first battleship and the first steel warship built at the yard, and in 1919 work began on the collier Jupiter to convert it to the Navy’s first aircraft carrier, the USS Langley. During World War II the yard employed nearly 43,000 workers.

The exhibits, displays, models and artifacts at the Portsmouth Naval Shipyard Museum ( delineate the yard’s long history with an emphasis on the 18th and 19th centuries. The Lightship Museum (see accompanying story) is associated with the Naval Shipyard Museum, and one admission fee allows admittance to both.

Spending time at the Children’s Museum of Virginia ( — the largest of its kind in the state — surely will bring smiles to the whole family while providing a learning experience for the youngsters. One of the more popular attractions is the Lancaster Antique Train and Toy Collection, featuring four layouts of running electric trains, plus an abundance of individual locomotives and cars. The pet park, a joint exhibit with the Norfolk Society for the Prevention of Cruelty to Animals, is dedicated to teaching kids how to care for pets. The planetarium, tot lot and the bubble room, where kids blow giant bubbles and can even step inside one, also are popular.

Sports buffs will want to venture into the new Virginia Sports Hall of Fame ( ), which opened earlier this year. With 35,000 square feet of exhibit space dedicated to baseball, football, soccer and basketball, there’s plenty to see. There’s even a simulator at the auto-racing exhibit.

For those with an interest in visual arts, the Courthouse Galleries ( offers a variety of exhibits encompassing Eastern, Western and multicultural traditional and contemporary art forms. It’s housed in an 1846 courthouse that’s on both the National Register of Historic Places and the Virginia Landmarks Register.

“There’s a lot of history in the city,” says Penney. “It’s part of what makes Portsmouth so special, and we’re dedicated to preserving it.”

But there’s far more to the city than that. Portsmouth offers much in the way of entertainment. There’s the restored 1945 Art Deco-style Commodore Theater, which shows first-run movies along with serving dinners. Concerts at NTELOS Pavilion at Harbor Center draw crowds to the 6,500-seat amphitheater. Concerts, musicals, dance performances and lectures are held at Willet Hall. Carriage rides and guided walking tours through the Olde Towne historic district also are a lot of fun. The visitor’s center has a brochure for self-guided walking tours with 45 points of interest.

The eclectic stores along High Street create a shopping Mecca worthy of exploration. Antique shops, boutiques, collectible and gift stores, art galleries, and more draw visitors and locals alike. As for dining, Portsmouth offers a variety of restaurants, from upscale to down-home country-style eateries where hush puppies — deep fried, seasoned cornmeal balls — rule. Favorites among cruisers include Brutti’s, a European-style bistro; the Bier Garden, featuring German cuisine and more than 300 kinds of bottled beer; and Baron’s Pub & Restaurant, famous for its burgers. Two coffee shops with Wi-Fi are the Daily Grind and Starboards Coffee Kiosk.

Special events occur year-round in Portsmouth. Of note is the Cock Island Race held every June. The two-day event draws more than 300 sailboats for the five-mile run from Mile Zero north to Middle Ground. “That’s a fun race for the serious guy, and it’s also fun for the less-serious guy who’s just out for a good time,” says Tidewater’s Shelton. “There’s a big party Friday night and an even bigger one on Saturday night.”

With so much to see and do, it’s a wonder that Portsmouth can maintain its relaxed atmosphere, where the tension after a long, hard passage simply ebbs away. But it does, and in fine Southern style. As its slogan states: “Portsmouth, The Right Place, The Right Time.”