From busy sidewalk cafés and tucked-away courtyard bistros to rooftop patios overlooking city views and scenic riverfront tables, the lure of outdoor dining beckons hungry people to enjoy great food and good times outside. In this segment of Patio Dining, we’ll do just that in and around Petersburg. Rich with history and wonderful cuisine, Old Towne and surrounding areas house some of the best eateries around. The following are a few noteworthy places to consider the next time you’re heading out for a meal.
<< Old Towne’s Alibi–305 N Sycamore St, Petersburg. For anyone looking to experience the casual charm of outdoor dining in Old Towne Petersburg, the cheerful, laid-back patio at Old Towne’s Alibi offers a remarkable place to enjoy the city’s character. This award-winning downtown restaurant serves generous portions of delicious pub fare, cocktails, and craft beer. Alibi’s popular brunch is frequently packed, with standout menu items including oversized mimosa flights, fried green tomato BLTs, and perfectly seasoned, extra-crispy fries.
The Boathouse at City Point >> 701 W Randolph Rd, Hopewell. Savoring a coastal-inspired dining experience provided by the chefs and staff at Boathouse is always such a delight! It’s tucked away right off the water in Hopewell with a lovely patio boasting live music and one of the most spectacular views of the Appomattox River, making this an excellent date night destination. Diners rave about the crispy brussel sprouts, corn and jalapeno hush puppies, as well as their shrimp and grits. Boathouse’s Creme brulee also gets high marks for dessert.
<< Tramonto Ristorante-322 N Sycamore St, Petersburg. Among the brick streets and historic buildings of Old Towne, Tramonto stands out for its authentic Italian cuisine and warm, welcoming setting. Guests love the old-world vibes on the rustic, bricked patio complete with fountain—very romantic! Patrons praise the generous portions, consistently high quality and friendly service. Crowd favorites include Tramonto’s homemade sauces and traditional dishes: lasagna, spaghetti with meatballs, stuffed eggplant, and chicken parmigiana—they’re all on the menu!
Shirley’s Bar and Restaurant and Twenty West Rooftop Lounge >> 20 W Tabb St, Petersburg. History, southern hospitality, and elegance all go hand in hand in the beautifully restored Hotel Petersburg, with two distinct and equally memorable outdoor dining experiences. The comfortable and inviting brick patio at renowned Shirley’s Restaurant is the perfect place to savor an upscale, delicious meal with outstanding service. Among their best-loved menu items are fried green tomatoes, spicy shrimp and sausage, as well as BBQ pork chops topped with an amazing apricot barbecue sauce. Shirley’s also serves an Au Gratin mac and cheese side that’ll rival the entree you pair it with—it’s really good!
Afterward or alternatively, head up to the hotel rooftop lounge and relax by the fire in cushiony comfort while taking in the city views below. It’s a fantastic place to be as the sun goes down and Old Towne lights up–talk about ambiance! Twenty West serves cocktails, local craft beers, and wines, in addition to elegant shareables and handhelds like hot dogs with kraut and crunchy onions, duck spring rolls, or soft giant pretzels served with jalapeno queso.
Editorial by Kim Amboy; June 2026