Experience the best of the best with this Top 8 list of things to do and see in Portsmouth.
Walk through history and see Olde Towne’s origins and it’s continued evolution.
Plan for your visit and explore Portsmouth with the Visitor Directory.
High Street is a central part of the Downtown Portsmouth National Historic District. It represents the town center, commercial core of what everyone now calls Olde Towne. If the National Register actually recognized drinking places, then the High Street corridor, along with a few blocks of each cross street, would definitely be on the list. In fact, Portsmouth’s drinking establishments can be traced back to the early 1700s when the Red Lion Tavern opened its doors to soldiers, sailors, pirates and the men who lived nearby. Upstairs, men slept 4 to a bed, while downstairs, there was food, spirits, and a cockfighting pit out back. Few know that cockfighting was sanctioned by the church in those days. The Red Lion Tavern building still stands today on London Street, although its most recent iteration is relatively young, only dating to 1820 and its current use is an office.
[box] Legend has it that the owner of the tavern, Mr. John Cornelius Portlock Edwards, a very colorful character, arranged his own funeral which was held on January 21,1896 at 2 am amidst the shrieks and howls of a drunken mob of over 500 people carrying torches and lanterns. He was buried standing up beside his two favorite horses and four dogs. Following the last prayer, the grave was bricked up, and the crowd left for refreshments and a cock fight.[/box]
Still Prohibition Party
High Street was mostly residential at that time. At the corner of Middle Street and High, there was a residence that’s now the Coffee Shoppe. In 1781, General Benedict Arnold made his headquarters on the upper level of this Federalist style basement home. In 1859, a single family home was built at 450 Court Street. During prohibition, the basement became a speakeasy. The home was later used for parties at the Catholic Club of Portsmouth. Today, it houses Still Worldly Eclectic Tapas, a basement, small-plate restaurant with original exposed brick walls and a large selection of whiskies. Still, as the locals call it, is well known for their costumed prohibition parties and other events consistent with the era of speakeasies.
Post Civil War, during the Reconstruction era, Portsmouth’s population grew tremendously. Norfolk had been destroyed during the war and was being rebuilt. Many of those doing the rebuilding lived in Portsmouth because the city had been spared and was in good shape with a sound drinking infrastructure for unwinding after a long day of rebuilding. This saw a new boon for development in the commercial corridor in and around High Street. Of note are two buildings, now serving food and drink. In the late 1880s, the Knights of Pythias, a secret, fraternal order founded in 1864 in Washington, DC, built their temple at 610 Court Street. This building, known as the Pythian Castle, is an excellent example of Romanesque architecture and, over the years, it has seen its fair share of drinks cross the bar, having been a variety of restaurants and nightclubs. It’s currently operating as Guads Mexican Restaurant, well known for delicious margaritas and other tequila drinks.
The other building of note constructed during this time is at 467 Court Street. Built as a Masonic Temple at the turn of the century, this four-story, Classic Revival building offered office space on the upper two floors, meeting and event space on the second floor and served as a restaurant on the first floor for many years. Today, it’s the Olde Towne Public House, known for a variety of beers, whiskies, and tequilas, not to mention wood-fired pizza, live entertainment, and an awesome street-side patio. Their St. Patrick’s Day party is a huge draw each year.
Gino’s Pizza is right next door at 455 Court St. in the original Building and Loan Bank constructed in 1922. Gino’s has a full bar and a street side patio, making for a fun warm-weather evening. The High Street Corridor saw the construction of many new buildings during this era, when shipyard workers arrived in droves to meet the growing needs of the military during the First World War. Cradock and Truxton are (now) historic neighborhoods built just to house the population influx, so the commercial center of Portsmouth had to expand to accommodate all the new residents.
It was the Second World War that brought the building boom to a close along High Street, particularly west of Middle. High Street was filled with theaters like the Lyric, the Commodore, the State, and the Colony. Dance halls, pool halls, locker clubs, honky-tonks, juke joints, backrooms, and more could all be found on and around High Street. The ferry terminal at the foot of High Street was bustling with people traveling to and from Norfolk. There were no tunnels at the time, so the Elizabeth River Ferry was the easiest way to cross. Throughout the 20s, 30s, and 40s, most all of the buildings standing along the High Street corridor today were built to accommodate the shopping and entertainment needs of the population. The ferry terminals are gone but the ferry still lands everyday, still bringing revelers to enjoy the High Street nightlife. Most of the buildings at the east end of High Street, by the water, were torn down in the 60s and 70s to make room for new and modern office buildings. The population, as in most American cities at the time, began their exodus to the suburbs, drawn by the allure of open space, privacy, and acreage, and leading them to Churchland, Western Branch, and Nansemond County. Then the tunnels were added and suddenly, it was an easy drive to the shipyard, hospital, and port for those who wanted to live closer to the ocean in Princess Anne County (now Virginia Beach).
But many of the buildings constructed back then survived and are now used for shops, bars, restaurants, apartments, offices, and more. Both the Commodore Theatre and the Portsmouth Hotel (now apartments) survived and still appear much as they did in 1945 when they were built. The Commodore Theater shows first run movies and provides dinner service with beer and wine available. Its careful restoration includes hand-painted wall murals, crystal chandeliers, restaurant style seating, and even the original ticket box. There is not a more elegant theater in all of Hampton Roads. Tower 507 was originally the Portsmouth Hotel. Today it houses apartment residents along with Humbolt Steel Corp., a bar with over twenty taps, a resident Great Dane, and some fantastic pizza. Also on the first floor is Cancun Fiesta, an authentic Mexican restaurant with the least expensive, top-shelf tequila on High Street.
Today, the High Street entertainment district offers 22 hot spots for drinks and social gatherings when visiting historic Olde Towne. From the very first block when arriving by water and west for eight blocks, there’s an abundant supply of restaurants and pubs. It’s an easy walk with things to see and places to visit along the way. Historic churches, the old Norfolk County Courthouse, the Olde Towne campus of Tidewater Community College, murals, sculptures, and ancient oaks come together to make the walk almost as much fun as the food and drink at your next stop. It’s a continuous pub crawl, especially on Friday and Saturday nights.
The pubs and bars throughout the district are all locally owned and operated. The bartenders and servers usually live close by. The entertainment showcases local musicians, DJs, and trivia hosts. Almost every night of the week, patrons find some type of music or game going on in most of the pubs. During the summer months, there is a big street party every Thursday night with bands, beer, wine, dancing, and good friends. Sunset Thursdays on the Water takes place at the foot of High Street from June through September starting at 6:30. After the show ends, people wander up High Street to find friends at their favorite watering hole. It’s truly a local’s night and a great chance to discover how the locals live in this quirky, old seaport.
Hardworking and Friendly Bartenders of High Street
The heart of High Street’s nightlife scene is the corner of High and Dinwiddie Streets. Seven of the twenty-two pubs and bars are located at this intersection. On Friday and Saturday nights, patrons are often seen shooting pool at Griff’s Restaurant and Sports Lounge, then grabbing a beer at Longboards’ lounge, checking out the music at Stellar Wine Co., and snagging a late night slice of pizza at Humbolt Steel Corp. Since the bars and restaurants at this intersection rarely have a cover charge, people move back and forth between businesses all night. Griff’s has a DJ just about every weekend night while Stellar Wine Co., an upscale wine bar, provides a variety of entertainment from jazz and acoustic to a Sip and Soul Saturday night DJ party.
Two of the oldest establishments at this intersection are Baron’s Pub and The Bier Garden Restaurant. Baron’s opened on High Street in 1988 and the Bier Garden in 1997. Both of these buildings were constructed around 1920, so they each have an old-school vibe. Baron’s serves American style food, including one of the best burgers anywhere and has an extensive selection of beer and spirits. Just about every night of the week, Baron’s brings in live entertainment, featuring local musicians and bands. They even do late night karaoke on Sunday nights. It’s a fun, local’s hangout no matter what time of day you go, whether it’s for lunch and a beer, after-work cocktails, or late night carousing.
The Bier Garden, locally owned and operated by the Osfolk family, is a classic German style restaurant known all over Hampton Roads for an amazing selection of imported beers. All totaled, there are probably over 400 different beers to try at the Bier Garden, including at least twenty on tap. Like Baron’s, the Bier Garden has its own unique feel and it’s definitely a place to find locals. The after-work crowd of regulars all seem to know each other. It’s not uncommon to find three generations of the Osfolk clan in the bar at one time. In addition to the bar, the restaurant provides several small dining rooms, a large front, covered patio, plus two outdoor patios for a great dining experience. The Bier Garden hosts local musicians on Saturday nights.
In between Baron’s and the Bier Garden is Longboards, known for beer, burgers, and specialty cocktails like Mai Tai, Blue Hawaii, and Tropical Itch. It’s a Hawaiian bar and grill featuring island cuisine with a tropical flair. Across the street is Stellar Wine Company, an upscale, small plate wine bar (with a few good beers too!) and an artsy, urban vibe. Cross over Dinwiddie St and there’s Humbolt Steel Corporation, a place to get California style pizza or try any of the forty or so beers on tap. And next door to Humbolt is Griff’s, another local hangout where you can watch sports, shoot pool, grab a burger, knock a few back with Allie at the bar, or check out the weekend DJ.
So while Dinwiddie and High might be the heart of High Street Nightlife, the big daddy of all the bars is just a couple blocks down toward the water. Roger Brown’s Restaurant and Sports Bar is the largest space on High Street, with a ninety foot bar, almost two dozen televisions and big screens, private event space, and a stage that fits a ten piece band – maybe more. Roger Brown’s has been known to have two or more parties on the same night!
Across the street, look for Sunshine behind the bar at her new club. She makes a wicked cocktail! The High is an upstairs private club that sometimes opens to the public for events. But downstairs is a hookah lounge, with beer, wine, and cocktails. There’s often a band or DJ inside on the weekends. If you like cigars and hookah tobacco, this is your place.
Another great place for live entertainment and specialty drinks is just around the corner on Court Street. The Olde Towne Public House American Bistro has an extensive menu that includes everything from stone-fired pizza to crabcakes and filet mignon. Public House has twenty taps, a curated beer list, and a shelf full of premium whiskies, along with the omnipresent PBR and Fireball for those who keep it simple. There’s a raucous street side patio and live music or DJs on the weekends. For those looking to watch some sports, check out the games on televisions all around the bar. Not what you would expect from a former 1920’s Masonic Lodge (or would you?).
Across the street from Public House is Still Worldly Eclectic Tapas Bar. While they rarely have entertainment, they are known for some pretty fantastic theme parties as well as beer, wine, and whisky dinners. Still is ideal for a quiet nightcap in a sophisticated setting. The entrance is on Queen Street which makes it a bit less obvious, but once there, it’s definitely worth the effort.
Two more nightspots bookend High Street. At the river, Legend Brewing Depot has awesome waterfront views, an outdoor patio, and hand-crafted beers produced by the oldest brewer in Virginia, Legend Brewing out of Richmond. At the Depot, they brew a few beers exclusively for this location too. If beer is not your thing, they do have a full bar. The menu is American style with great burgers and some excellent vegetarian options too.
At the other end of the street, in the 700 block, is Gosport Tavern. The Sunday night Jazz show is one of the best around if you’re a jazz enthusiast, and even if you’re not. Jamie, the bar manager is quite the mixologist and when time allows, there is nothing he likes more than fixing a personalized cocktail for his guests. The bar at Gosport has a great selection of beers and whiskies, along with a variety of other wine and spirits. The food is traditional tavern fare with burgers, sandwiches, soups, salads, meatloaf, ribs, and more.
Visit Portsmouth Virginia! The city is located in southeastern Virginia. A part of the Hampton Roads community of cites, Portsmouth is 30 minutes from the Virginia Beach oceanfront, less than an hour from Williamsburg, and we share a waterfront with downtown Norfolk. Don’t miss this Coastal Virginia treasure with its collection of antique homes spanning three centuries, its eclectic assortment of hip shops, edgy nightlife, and saucy, one-of-a-kind restaurants. Olde Towne is walkable, from the Children’s Museum of Virginia to the historic park at Fort Nelson and everywhere in between. Just park the car or show up by boat and head out on foot to explore this funky and friendly little city. Looking for a photo op? Take a walk on the Seawall at night and check out the best city light show in all of Hampton Roads. Portsmouth is a groovy little seaport with a happening art scene and an awesome music pavilion featuring the hottest touring bands. When you’re done with Olde Towne, take a ride to Midtown, Churchland, Truxton, Port Norfolk or any of our other historic communities and see what other offbeat places you can discover. Portsmouth is a laidback old city and a fantastic place to hang out for a day, a weekend, or even a lifetime.