Bars and Tasting Rooms

Whether you want to enjoy a night out with a few drinks and live music, find a sports bar to watch the big game, or indulge the senses with a wine tasting, there are a selection of bars and establishments in Chesapeake, VA to explore.

Live Music Bars

Seven nights a week, Eagles Nest Rockin’ Country Bar welcomes fiery newcomers and country superstars like Chris Stapleton to their stage. Taking a break from the show? Enjoy the mechanical bull, corn hole, and, of course, dozens of delicious drink options. Hungry? Plenty of tempting treats like nachos, burgers, or wings can be yours—there’s even an all-you-can-eat lunch buffet available Monday through Friday. 

Pull up a seat at the bar and settle in for a perfectly made, reasonably priced drink at Winston’s Cafe. One of the first businesses to take up residence in the Greenbrier area, Winston’s has been delighting customers with American classics and homemade desserts for more than 20 years. This hidden gem boasts karaoke and open mic nights weekly, as well as Taco Tuesdays, and chalkboard specials for lunch and dinner.

Sports Bars

Get ‘em boneless, breaded, or even bacon-wrapped—wings at Hooters are considered classics for a reason. Pull up a bar stool or grab a booth for hours of entertainment. And, with options like salads, fish and chips, and even a kids menu, you can bring the whole family!

Zino’s Italian American Restaurant is your go-to place for beers, cocktails, and frozen drink favorites to sip while cheering for your team. Try an order of Stingers Buffalo Bites along with a daiquiri, a margarita, or a Big Apple Colada from the attached Stingers Tavern.

With two Chesapeake locations—one by the water, one by the mall—you can’t go wrong with Big Woody’s Bar & Grill for beers, wings, and lots of sports. Take in the scenic view at the Great Bridge Lock Park location, or stop by for drink specials at the one by Chesapeake Square Mall. Both have terrific lineups to quench your thirst, feed your belly, and entertain the sports-addict within.

Tasting Rooms 

Sample wines, champagnes, and even sangrias at Branches Tasting Room, where you can savor glasses of reds, whites, and bubblies from around the world, as well as locally sourced drinks. This family-owned business will help you select bottles for an elegant affair or a simple dinner at home. Visit their website to check out events like Wine and Worship, painting classes, and even raffles. 

Offering 100 bottles of wine by the glass, Tinto Wine and Cheese will also impress you with their flawlessly curated selection of ever-changing cheeses and tapas, sure to pair beautifully with whatever’s in your cup. Inspired primarily by wines from Southern Europe, guests can also delight their taste buds with regional options from family-owned wineries. Planning to return to the area? Join the wine club for deals and discounts.