Dinner With a Side of Sunset: 12 Rooftop Hot Spots – Virginia’s Travel Blog

Who doesn’t love a great sunset? And how better to enjoy it than with someone you love to be with while enjoying drinks and dinner? Head for a rooftop for a memorable night out with someone special.

— COMMONWEALTH SKYBAR | CHARLOTTESVILLE —Commowealth Skybar on Charlottesville's Downtown Mall. Roy VanDoorn photo.

If love people watching, there’s not many spots better than Charlottesville’s downtown mall. Perch yourself a story above the crowd for a great vantage point paired with empanadas and a signature Skybar cocktail.


New to the Richmond restaurant scene, Kabana’s decor is reminiscent of Miami, with white tables, large lounge couches, and glass railings that come together to create a modern yet classic vibe. The Asian fusion menu has several different takes on Ramen, seafood options like the Grilled Octopus or Swordfish, and more basic (yet delicious) fare like the Wagyu Strip Loin. With being so new to the Richmond restaurant scene, it is almost always busy, and reservations are absolutely necessary to get a table for dinner. Aim at booking around sunset, as the views over Richmond and the James River are incredible during this time.

Previously known as the Iron Bridge Wine Company, The New Bridge may have changed names, but guests can still expect excellent food, attentive service, and perfect wine and craft beer pairings with their meal when they come to this rooftop restaurant. In old town Warrenton, the restaurant is elegant without being pretentious, and you’ll spot some ingredients growing right beside you on the building’s rooftop. The staff uses the herbs, greens, and edible flowers seasonally to infuse fresh flavors into the menu. If you are a fan of locally sourced beverages, ask for the wine list and pick out a bottle of Virginia wine to go with your meal.

A “family and friends” kind of hang out, Bouedreaux’s has a distinctly New Orleans vibe with menu items like red beans and rice, gumbo, remoulade, jambalaya, and low country shrimp and grits.


Good southern comfort food is what’s on hand at Supper. Enjoy it on the 3,000 square-foot roof overlooking the neighborhood of Ghent. Our culinary writer, Patrick Evans-Hylton, recommends the fried chicken, writing, “It’s flaky and crispy on the outside, moist and tender on the inside, and reminds us why we love being from the South.”
ALSO SEE: Hot Plate! 24 New Restaurants that Tempted Tastebuds in 2014 – Part 2

Grab some bacon wrapped shrimp to share with friends and toast the evening with a Virginia craft beer. This is quite the neighborhood hot spot, so you might reserve a table.


quirk rooftop bar
The huge 2,800-square-foot, two-tier rooftop space at Quirk Hotel is another recent addition to the rooftop scene in Richmond. Guests can order from a special food menu that differs from the one found in the lobby restaurant, and the rooftop location also has a bar menu that features unique cocktails, wines, and craft brews. The rooftop is only open for dinner and drinks, starting around 5 p.m. daily and serving until 10pm-12am, depending on the weather.


Twenty stories over the Virginia Beach Boardwalk is the very exclusive SkyBar. Membership is required to gain entry and the dress code is strictly enforced. If membership doesn’t sound exclusive enough, maybe a roped off VIP bed for lounging and sipping does. Menu is light fare. Check out the video.

The spacious rooftop patio at Postbellum is accented with lights strung above. It’s a great place to unwind with a charcuterie plate and a Virginia hard cider. Looking for something more filling? The menu features incredible dishes like local sausage and grits, smoked mushrooms, pan roasted salmon, and confit chicken. Many ingredients are Virginia-sourced.


As the evening winds down, you’ll stay toasty at Perch. Fire pits and complimentary throws are available to knock off the mountain chill. Appetizers and a beverage of your choice pair perfectly with steeple counting (a challenge issued by the Bolling Wilson).

Buzzfeed called it Virginia’s Most Popular Bar in 2013. It’s your turn. Go see what you think of Whitlow’s. Daily deals and happy hour offerings only add to its tiki bar appeal.


Capital Ale House has several locations, but the Harrisonburg location has a great rooftop deck you’re going to love. Pick a seat for your crew and then ponder which of the 100 draught selections you want to try with that plate of wings. If you’re there on a Monday, you’re in luck. Go straight for the burger menu as they start at $2!