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.
“Seize the moment. Remember all those women on the ‘Titanic’ who waved off the dessert cart.” ~ Erma Bombeck
“Sometimes a girl’s gotta have some chocolate!” ~ Carrie Underwood
“I love dessert. I can’t be guilty about it because I have to taste everything. I experiment.” ~ Martha Stewart
Portsmouth is known for its independently owned and operated restaurants. From diners to fine dining, these restaurants offer diversity and quality on par with restaurants around the world. Whether you’re looking for a romantic dining experience at a quiet corner table or a place the entire family will enjoy, Portsmouth will deliver. And if you’re one of those people who ascribe to the notion, “life is short, eat dessert first,’ then here is the perfect dessert trail for you to follow and indulge your passion for sweets. It will lead you from fine dining restaurants to casual cafes, a brewery, and even a couple of delightful bakeries. Bon appetit!
Address: 702 High Street / Neighborhood: Olde Towne
Mud-pie trifle features layers of house-baked brownies, chocolate pudding, whipped cream and Graham crackers. It’s a favorite for all ages and is easily shareable (but why would you want to do that?)
About Gosport Tavern: A gastropub serving American favorites in a relaxed setting. Known for an excellent selection of fine whiskeys and craft beers.
Address: 319 High Street / Neighborhood: Olde Towne
Vacherin is the quintessential French dessert. At Cafe Europa, it is presented as a white chocolate pistachio mousse tort with fresh strawberries, creme brûlée cheesecake on a ginger snap crust
About The Cafe Europa: Long considered one of the top restaurants in Hampton Roads, Cafe Europa features a wonderful selection of Mediterranean dishes and hand made desserts.
Address: 440 High Street / Neighborhood: Olde Towne
Homemade Grilled Pound Cake served warm. It’s glazed with an Orange Marmalade glaze and served with a fresh orange slice and whipped cream.
About Longboards Olde Towne: A cheery watering hole with a tiki hut vibe, this laid-back, casual dining restaurant is known for its burgers.
Address: 5700 Churchland Boulevard / Neighborhood: Churchland
JoJack’s signature dessert is the Summerberry Stack. It’s a layered dessert with key lime pie, white wedding cake, white Chocolate cheesecake, lemon mousse and fresh berries. Delicious!
About JoJack’s Espresso Bar and Cafe: Outstanding cafe known for a large variety of espresso drinks, specialty sandwiches, and homemade soups and salads, not to mention excellent pastries and desserts.
Address: 450 Court Street / Neighborhood: Olde Towne
Rich and chocolaty, this flourless chocolate brownie is made in house and served warm with salted caramel gelato.
About Still Worldly Eclectic Tapas: With the feel of an old-time speakeasy, Still (as the locals call it) is known for inventive cocktails, fine whiskies, and a wide variety of small plate offerings.
Address: 438 High Street / Neighborhood: Olde Towne
Prepared and baked daily by veteran head waiter Russell, phyllo pastry is filled with freshly cooked apples, seasoned and topped with cinnamon, baked until golden brown and served warm with Whipped Cream.
About The Bier Garden: A High Street staple for over twenty years, The Bier Garden is known for homeade German dishes and a large selection of imported beers.
Address: 425 High Street / Neighborhood: Olde Towne
Made in house, this signature dessert is both tasty and gluten free . It is a flourless chocolate torte with chocolate ganache.
About Stellar Wine, Co.: Sophisticated and warm, Stellar Wine Co is known for its curated wine selection and incredible New Orleans inspired small plates.
Address: 615 High Street / Neighborhood: Olde Towne
Diabetic friendly, dairy free and gluten free, this Flourless Double Chocolate Vegan Cake is made without flour. The cake batter is made using quinoa and cacao topped with an avocado based cacao frosting. It’s a great plant based protein and a delicious dessert!
About Beyond Vegan Cell Food Cafe: Focused on healthy living, Beyond Vegan Cell Food offers a wide variety of meatless (and soy-less) sandwiches and entrees. It’s a quaint cafe offering smoothies, healing teas, alkaline bowls, soul food specialties, and much more.
Address: 1 High Street / Neighborhood: Olde Towne
You’ve heard of a Root Beer Float? Well, try it with a locally brewed Porter instead. Porters are dark beers made using rich malted barley giving them somewhat of a sweet, chocolaty flavor. This provides the perfect, creamy taste when mixed with ice cream. (You can also try it with the limited edition Chocolate Raspberry Stout). It’s great on a hot day!
About Legend Brewing Depot: A waterfront restaurant located on the High Street Ferry Landing, Legend Depot is the first expansion of Legend Brewery, the original craft brewer in Virginia. It is known for burgers, sandwiches, excellent appetizers, vegetarian options, a beautiful setting, diverse beers, and a laid-back pub atmosphere.
Address: 316 High Street / Neighborhood: Olde Towne
Our secret family recipe has been wowing our customers for 20 years. Delicious spiced apples and a crunchy cobbler crust are topped with vanilla ice cream and caramel. Guaranteed to please.
About Roger Brown’s Restaurant and Sports Bar: A casual sports bar serving Southern-leaning comfort foods, Roger Brown’s is known for seafood, steaks, burgers, and salads. 24 beer taps and lots of big screen televisions, it’s a place where the game is always on!
Address: 337 High Street / Neighborhood: Olde Towne
A delicious combination of two favorites! Fresh bananas blended into our traditional cheesecake, layered full of Nilla wafers with a graham cracker crust
About The Lobscouser Restaurant: A High Street favorite since 1987, Lobscouser is well known for its seafood dishes, like Scallops Smithfield and Crab Meat Portsmouth. The “He-Crab” soup is legendary. Lobscouser attributes its longevity to always providing quality food at a fair price.
Portsmouth is fortunate to have two bakeries owned and operated by locals who take baking to a whole new level. Whether you’re looking for cakes, pies, pastries, or something custom, just for your occasion, these two businesses will not disappoint.
Address: 4715 Portsmouth Boulevard / Neighborhood: Alexander’s Corner – City Park – Victory Crossing
Custom Cakes from Silver Spoon
C.C. (Claire) Martinez has owned and operated Silver Spoon Bakery and Gourmet Gifts for over ten years. She developed her love of baking as a child with her Easy-Bake Oven and is now best known for her luxury pound cakes, artisan cupcakes, and her special occasion and wedding cakes.
While custom and wedding cakes are all unique and made to order, there are always an assortment of treats in the shop. You will find a variety of cupcakes, and more often than not, you’ll find a few pound cakes (try the lemon!), bread pudding, brownies and bars, krispy rice treats, cake pops, and maybe even some chocolate covered bacon.
So ring the bell and come on in. You will be glad you did!
Learn more at the Silver Spoon Bakery website.
Address: 333 High Street / Neighborhood: Olde Towne
Petite Sweets Small Desserts
The new kids on the block, proprietors Sheryl Harris and Denita Twine are passionate about baking. They believe in little desserts with big flavor! You will always find a variety of jarred desserts, cupcakes, and single-serving pies. To keep it fresh, they like to change up the offering. Some days, you might find key lime pie, banana pudding in a jar, and vanilla cupcakes, while other days, you will find red velvet brownies in a jar, cookies and cream cupcakes, and lemon custard pie. And then there are times when you might find it all. The idea is to have you keep coming back to see what deliciousness they have prepared anew. You can pre-order larger quantities and they provide custom orders as part of their catering service.
At Petite Sweets, their mission is to bring joy to each and every customer who walks through the door. They also love to share their passion for baking. So stop in, say hello, and grab their latest petite sweet!
Learn more at the Petite Sweets website.
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 urban 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 laid-back old city and a fantastic place to hang out for a day, a weekend, or even a lifetime. Check it out!