The Coolest Neighborhoods in Pittsburgh, Pennsylvania

Randyland art gallery, in Northside, Pittsburgh, is a fun place to discover local street art
Randyland art gallery, in Northside, Pittsburgh, is a fun place to discover local street art | © Michael Ventura / Alamy Stock Photo
Photo of Natasha Bazika
10 May 2021

Each of the 90 neighborhoods in Pittsburgh has a distinct personality. Also known as the City of Bridges – there are no fewer than 446 – this Pennsylvania city boasts skyscrapers, reinvented public spaces, river fronts and museums all part of its collective landscape. Why not book a visit to the Steel City through Culture Trip and see for yourself.

North Shore

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Andy Warhol self-portrait at Warhol Museum, Pittsburgh, Pennsylvania
© Philip Scalia / Alamy Stock Photo

It’s not just worth heading to North Shore for its famous sports venues but also for some of the city’s best museums. Check out the Andy Warhol Museum, National Aviary, Children’s Museum of Pittsburgh and the Carnegie Science Center, before heading to the extraordinary Randyland. A once-dilapidated building, it’s now an art museum like no other and the most colourful building in Pittsburgh.

South Side Flats

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E98X76 MURAL DOUBLE WIDE GRILL RESTAURANT EAST CARSON STREET SOUTH SIDE FLATS PITTSBURGH PENNSYLVANIA USA
© Russell Kord / Alamy Stock Photo

One of two neighbourhoods in the South Side of Pittsburgh, the South Side Flats is next to the Monongahela River and is a must-visit after dark. The area is centred around East Carson Street, a National Historic District of Victorian buildings packed with bars, music venues and cafes. Don’t miss cocktails at elegant speakeasy Acacia or, if you like things a little noisier, Jack’s Bar is the stuff of local legend for its noisy jukebox, pool tables and friendly staff.

Brookline

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Brookline is a family-friendly neighbourhood crammed with restaurants, art galleries, great schools and two city parks. Kids will love the playground at Brookline Park and ice-cream sundaes at Scoops on the Boulevard. Meanwhile, grown-ups will be happy with the taco stall at Las Palmas Carniceria and artisan coffee at 802 Bean Company. And there’s also the legendary Pitaland, which draws crowds for its fresh pita bread and hummus.

Squirrel Hill

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2B8PPFB The Forbes Avenue business district in the Squirrel Hill neighborhood on a sunny winter day, Pittsburgh, Pennsylvania, USA
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The residential neighborhood of Squirrel Hill, in the East End of Pittsburgh, is known for its pizza spots like Aiello’s and Mineo’s, along with its diverse culinary scene. Movie buffs will enjoy visiting the Manor, one of Pittsburgh’s oldest movie theaters, which features a popular bar. Plus, if you love the outdoors, the neighborhood is sandwiched between Frick Park and Schenley Park, offering easy access to green space.

Bloomfield

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GN42K7 Three men move a Sicilian cart carrying a religious statue at the Little Italy Festival in Pittsburgh's Bloomfield neighborhood.

For its affordability, Bloomfield, also known as Pittsburgh’s Little Italy, is a favorite among college students, from local universities such as Carnegie Mellon and the University of Pittsburgh. Eat out at the revered old-school Italian restaurants plus, if you’re staying for long enough, try the local Thai and Vietnamese spots, too. This hip destination prides itself on Liberty Avenue, where you can rifle through classic vinyl records, pick up books by local authors or trade in and buy preloved clothes. Bloomfield also hosts a variety of popular annual events, such as parades for Columbus Day and Halloween, and Little Italy Days in August, where Liberty Avenue comes alive with vendors, Italian food and entertainment.

Lawrenceville

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2DECWBN PITTSBURGH, USA - JUNE 30, 2013: Street view of residential area of Lawrenceville, Pittsburgh. It is the 2nd largest city of Pennsylvania with populat
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Lawrenceville, formerly an industrial neighborhood, has been transformed into a hub for innovation, creativity and nightlife. There are plenty of local retailers, cute breakfast and brunch spots, and a selection of places to grab a drink; Church Brew Works is the oldest brewery and draws in huge crowds with its unique space in a historic church. For entertainment, catch a show at Row House Cinema – a single-screen theater that picks movies based on a weekly theme – or head down to the Arsenal Bowling Lanes.

Strip District

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EJWN7B Wholey meat market in Pittsburgh PA
Wholey meat market in Pittsburgh, PA. | © Randy Duchaine / Alamy Stock Photo

Strip District, aka the Strip, is foodie heaven. Start the day with a classic breakfast at Pamela’s or grab a coffee from some of the best coffee shops in town, such as La Prima and 21st Street Coffee, where they brew Intelligentsia beans using a variety of trendy techniques. Meanwhile, lunch could take you anywhere, from fish at Luke Wholey’s to spicy tacos at Edgar’s, before the evening is rung in at Wigle Whiskey, which makes a variety of organic grain-to-bottle spirits, and Maggie’s Farm, which distills award-winning rums.

Shadyside

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2CFYYRW Pennsylvania Pittsburgh Shadyside Kentucky Avenue home homes house houses residences neighborhoods neighborhood sidewalk couple walking residents
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Come to Shadyside to gawp at the Victorian-style mansions that line Fifth Avenue. Green space and parking are considered a premium in the neighborhood, but Mellon Park is just around the corner and offers a beautiful open space with a walled garden and various sports fields and courts. As for cuisine, Shadyside has it all – from casual dining like Stack’d, which serves great burgers, to fancy eats such as Casbah or Soba for upscale Asian cuisine. Elsewhere, shop until you drop on Walnut Street, featuring high-end retailers to eclectic locally owned stores. One of the biggest attractions in Shadyside is the Jams on Walnut, summer concert block parties, which draws thousands of people to the neighborhood.

Siobhan Grogan contributed additional reporting to this article.

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