Sherree Goldstein moved to Regent Square in the late ‘90s when there wasn’t a lot happening in the business district. “There was a pizza place and a lot of bars, but it wasn’t thriving. Everybody was just getting by.”

For five years, she searched the city for a space to open a restaurant but couldn’t find just the right fit. Then in 2003, a storefront opened in her neighborhood. She signed a lease and six short weeks later, The Square Cafe opened its doors.

Neighbors came in droves to the colorful breakfast and lunch spot to try the breakfast quesadillas, veggie scrambles and brussels sprout hash. And they’ve been coming ever since.

“When The Square Cafe opened, that definitely changed things. It gave us a place to come together for breakfast,” says Joe Davis, owner of the newer coffee shop Biddle’s Escape, down the street. As word spread, the Square Cafe made Regent Square a destination for diners.

Today, the café is but one of many destination spots in the neighborhood.

Four municipalities make up the vibrant and now highly desirable Regent Square—Swissvale, Edgewood, Wilkinsburg and the city of Pittsburgh—with Frick Park bordering this rectangle-shaped plateau on one side. Because the neighborhood is less than one square mile, every house in Regent Square is within walking distance to the 644-acre park.

Chillin' at the Frick Park Dog Park. Photo by Brian Cohen.

Chillin’ at the Frick Park Dog Park. Photo by Brian Cohen.

“Making the park better changed everything,” says Joely Heidinger, a resident for 17 years, who refers to the massive cleanup that began in 1995. “Frick Park is what makes people love Regent Square.” In addition to nature trails, the park features baseball fields, a playground, the city’s only red clay tennis courts and a fenced-in dog park with a creek.

People also love the walkability of the town. Large sycamores shade the appealing streets lined with Pittsburgh four squares, Craftsman bungalows, Victorians and Colonial Revival homes. “It’s like a small town in the city,” says Heidinger. “I call it Mayberry. It’s got all the perks of the city but few of the problems.”

It also has a bohemian and intellectual flair that sets it apart. Consider: The restaurants cater to vegetarians, the highly regarded Environmental Charter School resides here the award-winning Pittsburgh Center for Complementary Health and Healing offers a host of wellness therapies like massage, Reiki and acupuncture. Around 46% of the population holds a master’s degree—or higher. And to cap it off: The shopping district boasts no chain stores or chain restaurants.

Things to do in Regent Square

Regent Square is known for its quaint older homes. Photo by Erika Gidley

One favorite, D’s Six Pax & Dogz, has built a loyal following over the years. D’s—which opened in 1999 by the owners of nearby McBroom’s beer distributor—serves dogs in beef, turkey, brat, kielbasa or veggie varieties with unexpected toppings like Sriracha slaw, mac and cheese and avocados. When one of the 27 kegs kick, they replace it with a new variety. You can drink—or make mix-and-match six packs at The Beer Cave—from more than 1,200 craft beers and microbrews. And kids can indulge in root beer, always on tap.

At Root 174, opened to acclaim in 2011, chef Keith Fuller has helped put Pittsburgh on the national food map with his creations of locally-sourced and seasonal meals with outstanding vegan offerings, such as the popular vegan meatloaf.

“Because we are a small restaurant, Keith can experiment,” says business partner Patrick Bollinger, drummer for the band Anti-Flag. “We were doing a bone marrow creme brûlée—that type of creativity and bringing old world things to the mainstream is what Keith does amazingly well.”