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City Guide: 200+ Fun Things to Do in Pittsburgh (No Matter Where You Are)

We explore every inch of Allegheny County (and beyond) for a look at the communities where we live, work and play.

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Photo by Dave DiCello



Ever seen a postcard depicting the Pittsburgh skyline? Chances are that photograph was taken from Mount Washington, a peak perfectly positioned against the confluence of the three rivers. There also is much to see on and around the hilly terrain and at its base. The South Side, at the foot of the mountain, is the city’s unparalleled nightlife district. Above it, steep and winding roads lead to several homey neighborhoods.


What's Here?

South Side Flats: The bar scene in this riverside area has everything from low-fidelity dives to hipster joints to high-energy dance clubs. The fun-loving atmosphere extends to eateries, arts venues and tattoo parlors.

South Side Slopes: Well separated from the action below, the South Side Slopes offer residents a quiet life enhanced by three sizable parks.

Mount Washington: This high-altitude neighborhood’s key asset is its eye-popping view of the city skyline. Along Grandview Avenue, upscale restaurants and luxury housing take advantage of the backdrop. In their shadow, a close-knit community enjoys its relative isolation from the hustle and bustle below.

Duquesne Heights: To the west of Mount Washington, this neighborhood enjoys the same breathtaking view and easygoing lifestyle. Olympia Park takes up much of its acreage.

Allentown: Rail lines still are embedded in the main drag of East Warrington Avenue as a remnant of the days when electric street cars transported residents to and from more central parts of the city. The area has faced economic hardship but has held onto local businesses.

Arlington Heights: Roads long and winding up the hillside bisect this mostly residential neighborhood.

Arlington: Similar to Arlington Heights (though flatter), Arlington is comprised mostly of working-class homes.

St. Clair: One of Pittsburgh’s smallest neighborhoods, St. Clair today claims just a handful of streets and about 200 residents.

Mount Oliver Borough: This slice of territory is a civic anomaly as an independent municipality within Pittsburgh city limits. It includes a business district along Brownsville Road.

Mount Oliver: To further complicate things, there is a tiny neighborhood of the city called Mount Oliver next to (and largely indistinguishable from) the borough of Mount Oliver.

Knoxville: Once the site of a strawberry farm (protected from air pollution by Mount Washington), Knoxville began amassing residents in the mid-20th century and still has slews of homes arranged in close proximity.

Beltzhoover: This area is undergoing a major effort to revamp its housing stock. Fun fact: The name comes from a German-born farmer who once owned most of the land.

Bon Air: While it may seem as if this secluded, almost-suburban neighborhood’s only connection to the big city is its lone “T” stop, Bon Air is a happy home for many city families, with beautiful views aplenty.

Carrick: One of Pittsburgh’s larger neighborhoods in terms of geography, Carrick sits on the city’s southernmost edge and sports independent hardware stores, no-frills pubs and family-owned pizza shops along its well-trafficked streets.


10 Fun Things to Do


1. At the foot of the South Side Slopes sits Games N’ At
 [2010 Josephine St.], a vintage arcade modeled after those in malls of yore. It has all of the ’80s video classics (Space Invaders, Donkey Kong, Pac-Man, etc.), plus air hockey, table tennis, skee-ball and pinball.

2. Want to do a pub crawl? The South Side Flats is the place! Hit up the Double Wide Grill, the Carson Street Saloon, Piper’s Pub, Club Café, Diesel Club Lounge, Brewski’s, Lava Lounge, Jekyl & Hyde, OTB, Fat Head’s, Coppertops, Jack’s, Dee’s, Casey’s, Jimmy D’s, Mario’s or Mullen’s — to name fewer than a third of your options.

3.  Each year, City Theatre [1300 Bingham St.] 
puts on a full season of recent, invariably brainy works. City’s latest productions include “Tribes,” Nina Raine’s exploration of “deaf culture,” and “Grounded,” George Brant’s one-woman show about an Air Force pilot-turned-drone operator.

4. The South Side Flats also is home to the only public boat launch within the city at South Shore Riverfront Park. Kayakers, canoeists and motorboat owners appreciate the launch — but this also is a place for fishing and providing the dog with some aquatic relief in the summer.

5. Though Mount Washington’s patch of prime scenery-gawking terrain is well-developed and cluttered with visitors, Duquesne Heights has green space and open sidewalks — ideal for a picturesque sunrise jog.

6. Chatham Village, an oasis of red-brick homes and ample yards on Mount Washington, is considered one of the best-planned and -preserved examples of the 1930s “garden city” movement. Architecture aficionados should schedule a walk through the community.

7. Just as no visit to San Antonio is complete without a tour of the Alamo, a stop at a Mount Washington observation deck is a must for Pittsburgh’s tourists and newcomers. Get an eye of that skyline, with the rivers unfolding from the Point beneath a seemingly endless succession of bridges.

8. McKinley Skate Park [Bausman Street] in Beltzhoover is one of three municipal skate parks in the city. It arguably is the most challenging, with ramps, half-pipes, splines and rails.

9. Though it exists outside of any well-known dining district, many local foodies insist that Allentown’s Alla Famiglia [804 E. Warrington Ave.] is the best Italian restaurant in the city, with its decisively Old-World style of cooking and its gargantuan portions.

10. What better way to experience a working-class neighborhood than heading to the bowling alley? Check out Carrick Classic Lanes [2036 Brownsville Road, 412/885-2880]. The attached bar, Whoville’s, helps to modernize the old ball-and-pin routine with a selection of craft beers. —Nick Keppler


Insider Tips

For Visitors: At night, the South Side Flats can get . . . let’s say “rowdy.” To avoid the chaos, go on a Sunday afternoon. Everything is open, brunch options are plentiful, buskers take to the streets and bar-goers play tailgate toss outside their favorite watering holes.

For Newcomers: This region has its own weekly independent newspaper, the South Pittsburgh Reporter, published continuously since 1939 and available at no cost in several locations across these neighborhoods. Not just a place for pictures of adorable preschoolers from local parades, it delivers sharp reporting on development and property-related legal battles.

For Residents: Bon Air and Carrick both have active neighborhood groups. The Bon Air Civic Association and the Carrick Community Council both plan picnics, block parties and cleanup days, and they help to organize residents in anticipation of school funding or transit cuts. —NK


Brazen Kitchen's Picks


Skip the chains and college bars and sample a changing South Side. Amazing Café [1506 E. Carson St.] is a groundbreaking oasis with food that redefines what “healthy” can taste like. The café makes sophisticated smoothies and serves them with a bamboo straw; the fare is so artfully made and presented that you simply must take a photo before you dig in.  

Piper’s Pub [1828 E. Carson St.] is a gastropub with a well-curated beer and drink selection, as well as an English comfort-food menu that surprisingly is vegetarian-friendly.

The Zenith [86 S. 26th St.] is the embodiment of the South Side’s charming quirks — you’ll need to wind through an antique store to reach the small restaurant.  —Leah Lizarondo

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