A Youth Movement is Leading a Resurgence on the Hilltop

The cluster of neighborhoods resting above the South Side offers amenities, surprises and affordable homes.

Hilltop Allentown Sign

If you’re not in the habit of studying elevation maps of the greater Pittsburgh area — probably a bit of a niche hobby — you may have never truly considered the towering mountain cradling the city.

Beginning with the famous inclines on the banks of the Monongahela and stretching toward the South Hills, the series of neighborhoods and municipalities above the city include famous vistas and landmarks such as Mount Washington’s iconic Grandview Avenue. Far from the tourist spots, however, a series of city neighborhoods including Allentown and Mount Oliver — collectively, if informally, known as the Hilltop — are resurgent, hiding some of the city’s well-kept secrets.

Hilltop Wizard


Increasingly, however, those secrets are getting out.

“The new generation of people, the young people coming in, it’s amazing,” says Maria DeSimone Prascak, an artist who shares studio space in Mount Oliver with her husband, fellow artist Johno Prascak. “I grew up right down the street,” she says, and worked in her father’s contracting office — the same building that now serves as her studio.

The Prascaks bought “an old Victorian” home in Mount Oliver, close to Maria’s childhood home and their studio. (Mount Oliver refers to two areas — a small city neighborhood and the neighboring borough of the same name.) “It was the big Eddie Munster house we were afraid to go to as kids,” she jokes; the couple restored the home years ago.

“Everyone’s buying the houses up; we’re the old people on the street now.”

Hilltop Street

Mount Oliver and Allentown, two neighborhoods linked by Arlington Avenue, are each home to resurgent main streets.

In Allentown, the theme is decidedly gothic. Near the corner of Arlington and East Warrington avenues, neighborhood flagship Grim Wizard Coffee — recently renamed, but essentially unchanged, from Black Forge Coffee House — offers friendly service and industrial music in equal measure. Down the streets, spooky boutique The Weeping Glass draws visitors from far and wide, while “time-inspired specialty shop” Dr. Tumblety’s sells spiritualism-themed apparel and products (and houses a secret speakeasy).

Hilltop Brown Bear


Brownsville Road, meanwhile, leads visitors through Mount Oliver foodie destinations from the old-school to the cutting-edge. The new Brown Bear Bread Cafe bakes irresistible offerings, while Flavor of Puerto Rico serves up tasty rice-and-meat-focused meals. Maietta’s Restaurant has served pizza to multiple generations; around the corner, ECHT Coffeehouse Lounge and Bistro offers thoughtfully prepared espresso drinks and breakfasts.

The area is also emerging as a cultural hub thanks to the varied programming at Bottlerocket Social Hall, a throwback bar that hosts nightly events including comedy, music, trivia and plenty of unclassifiable gatherings.

And all the Hilltop neighborhoods share one common trait: Breathtaking views, often around unexpected corners. The views of the city are unrivaled, even by the much-hyped vistas in Mount Washington.

Hilltop Tumbletys


You’d be forgiven for assuming that resurgent main streets, beautiful views and a convenient location — Downtown is less than a 10-minute drive — have driven housing costs up. Good news for buyers and renters, however: You can still get a deal up here (if you don’t mind an older home). According to realtor.com, the median home listing price in Allentown is just $122,000. In the neighboring South Side Slopes, the median listing price is a still-low $185,300 — and that number is driven up by some pricier new builds toward the bottom of the hill.

The rolling hillside conceals well-kept secrets, from patches of green space to tucked-away streets. And while you can easily find a quiet corner to live in, you’re a short walk away from a thriving main street — or two.

“You can feel the energy and the positive things happening,” Prascak says. “This is a little community … it’s just wonderful.”

Early 19th Century

Allentown Population

Mount Oliver Population

Mount Oliver Borough Population

Did You Know?
Mount Oliver Borough is the only independent municipality completely surrounded by the city of Pittsburgh. Residents fought against annexation when neighboring boroughs were becoming part of the city around the turn of the previous century.

Categories: Neighborhoods