Bars in Penn Hills

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At Pittsburgh Improv, comics lure laughs from bellies in the hopes of following in the footsteps of standup legends such as Ellen DeGeneres, Chris Rock, Jerry Seinfeld, and Dave Chappelle, all of whom have graced the Improv club stages. The calendar schedules comedians as often as six nights a week, alternating between big-name headliners and up-and-comers who tickle funny bones with fresh material, abundant energy, and feathered reflex hammers. Audience members munch on their choice of a savory appetizer, such as spinach-and-artichoke dip or buffalo wings, while sipping a cocktail to avoid eye contact with the giant rubber chicken sitting at the next table.

166 East Bridge Street
Homestead,
PA
US

At Bossa Nova, it’s okay to begin a meal with cupcakes. In the baked chicken cupcakes—one of many tapas plates on the menu—mashed potatoes are substituted for frosting, and there’s a garnish of sautéed zucchini. Such innovative recipes are mixed in with a number of classic ones; you can also try fried calamari, spicy tuna tartar wrapped in cucumber, and a bacon, brie, and potato sandwich. These dishes are centered on a communal dining experience, which encourages you to try whatever tapas plate your friend is eating without first pretending to have somehow misplaced your own. In addition to tapas, the kitchen serves up larger entrees such as Spanish chorizo and beef filet.

The restaurant's space is just as eclectic as the cuisine, with a circular bar covered in mosaic tiles acting as the centerpiece. Stop here to order wine and cocktails, and on Thursday, Friday and Saturday nights, guests head to the dance floor during DJ sets. Chandeliers and vibrant artwork surround the tables spread throughout the dining room, and there are nooks embedded into the walls if you want a more intimate setting.

123 7th St
Pittsburgh,
PA
US

The dessert-inspired martini list at Olive or Twist hosts a range of sweet digestifs including the cake-batter cocktail, the tiramisu martini, the chocolate-covered-pretzel martini with a salted rim, and the key-lime-pie martini. In addition to inventive mixes, Olive or Twist hosts a wide selection of craft beers, ensuring guests find the ideal beverage to compliment upscale American fare from the full kitchen. Its range of appetizers and entrees sate any size of appetite, with options such as truffle fries, housemade crab cakes, and filet mignon with peppercorn sauce. While they dine, patrons can feast eyes on the dark-mocha wood accents that lace the bar and lounge areas at Olive or Twist, offsetting the cream-hued plush seats.

140 6th St
Pittsburgh,
PA
US

Opening on weekdays at 4:01 p.m. and Saturdays at 11:31 a.m., Shiloh Grill reminds visitors that patience will be rewarded. The restaurant?s most popular offering, the Thanksgiving in Blawnox, consists of half a pound of ground turkey topped with dried cranberries and sage stuffing mixed in and rosemary aioli on top?a year-round reminder of autumn that balances out the ever-rotating seasonal menus and selection of craft brews. Several events also run throughout the week.

123 Shiloh St
Pittsburgh,
PA
US

The cooks at Harris Grill populate their menu with American classics. They've got a bacon cheeseburger by the name of The Burghermeister Meister Burgher, a dish of marinated chicken skewers dubbed Britney Spears, and a grilled pork dish called Prime Pork Flatiron. To complement seasonal entrees and keep patrons on their toes, the selection of draft beer rotates often.

5747 Ellsworth Ave
Pittsburgh,
PA
US

In 1938, J. Oliver Wintzell opened a tiny seafood joint on Dauphin Street in historic Mobile, Alabama. With room for just six customers to hop up on barstools and sample oysters prepared in three signature styles?"fried, stewed, or nude"?the eatery harbored modest ambitions and kept itself in check with walls strewn with Oliver?s homespun sayings. Oysters this great can?t remain a secret for long, though, and Wintzell?s Oyster House began to grow at such a rate that Oliver was compelled to expand to new locations throughout Alabama and beyond?by bringing the tastes and flavors of the Gulf Coast to Pittsburgh.

Despite the restaurant?s rapid growth, remarkably little has changed since those early days. Oliver?s wit and wisdom still cover the walls, and the menu still tempts with its stuffed crabs, USDA-certified steaks, and signature oysters. In keeping with the cozy atmosphere Oliver cultivated by necessity more than 70 years ago, shuckers stationed at the oyster bar chat with diners as they garnish half shells with hickory-smoked bacon and slap away the tentacles of sneaky krakens. Tom Bross of Delta's Sky magazine has some helpful words of advice for first-time visitors to the restaurant: "Let the Southern hospitality, laid-back tempo and maybe a cold one help you unwind."

530 E Bruceton Rd.
Pittsburgh,
PA
US