This upscale neighborhood is home to hip events, culturally diverse restaurants, and one of the only remaining wooden streets in the country.

Welcome to Shadyside

Upscale luxury meets historic Victorian character in a bustling neighborhood
One of the most centrally located and walkable communities in Pittsburgh, Shadyside boasts beautiful residential spaces of imposing Victorian homes and a bustling business district featuring high-end retailers and eclectic boutiques. Located on the east end of Pittsburgh, this upscale neighborhood is home to hip events, culturally diverse restaurants, and one of the only remaining wooden streets in the country. Roslyn Place, off Ellsworth Avenue, features 26,000 oak blocks “paving” the road!
Originally a farmland community, Shadyside has experienced many different faces throughout the last few centuries. The neighborhood began its residential growth in the late 1800s through the 1950s and became a haven for hippies in the ‘60s and ‘70s. Shadyside was so popular it was once called “Pittsburgh’s Greenwich Village.” Today, Shadyside is home to stunning Victorian homes, tree-lined streets, and plenty of shopping opportunities. The neighborhood is just six miles away from downtown Pittsburgh, offering easy access to a larger city just outside of the suburbs.

What to love

  • The Summer Jam on Walnut concert series
  • Eclectic boutiques in three separate business districts - Ellsworth Avenue, Walnut Street, and South Highland Avenue
  • Breakfast at local hotspot Pamela’s Diner

Local Lifestyle

There is always something to do or experience in Shadyside. Modern and upscale amenities mixed with the old architectural character of the Victorian homes provide a unique living experience for residents of Shadyside. Young professionals, families, students, and artists blend the old with the new to create a unique and thriving neighborhood. From dozens of outdoor festivals to luxury dining experiences set along old-fashioned streets, Shadyside is a fun and vibrant place to call home.

Dining, entertainment, and shopping

With three business districts to choose from, Shadyside offers plenty of dining, entertainment, and shopping options. Hungry for a mouthwatering breakfast? Look no further than Pamela’s Diner, an award-winning restaurant that makes the best pancakes and provides the best service. Pamela’s Diner has been in business since 1980, and guests are welcomed with a cheery atmosphere and delicious menu options. Try their famous crepe-style hotcakes or homemade Chorizo hash!
Prantl’s Bakery is another Pittsburgh institution and is home to the Burnt Almond Torte, which is the “best cake in America,” according to the Huffington Post. Offering over 100 bakery items, Prantl’s is one of the country’s best bakeries and the winner of dozens of awards from companies like Food Network and Trip Advisor.
Using locally sourced ingredients and a menu of small plates meant to be shared, Soba cooks from the heart. Pulling inspiration from Japan, South Korea, China, and Thailand, Soba fuses classic Asian dishes with a modern twist. Rated as one of Pittsburgh’s finest restaurants, Soba brings an upscale and decadent menu to Shadyside.
For “Funky-fresh Cal-Mex,” visit Mad Mex, an American mix of Mexican, Southeast Asian, and Spanish dishes made from scratch each day. They offer healthy and fun meals with big flavors, big plates, and beer and tequila to wash it all down. Mad Mex is the perfect spot to relax with a burrito and a group of friends.

Things to do

Walnut Street is the heart of Shadyside and offers dozens of events throughout the year. Jam on Walnut is the most anticipated event of the summer in Shadyside. The summer concert series is held every Saturday on Walnut Street and offers food, drinks, and activities with proceeds benefiting local charities.
If you’re looking for a truly unique and fun event, Shadyside hosts the Walnut Street Invitational Car Show every year. Over 130 rare and vintage cars make their way through Walnut Street a few days before the Pittsburgh Vintage Grand Prix. Cars are selected by invitation only, and residents can walk down Walnut Street to meet the owners and learn more about each model.
Another popular Walnut Street event is the Arts Festival held each summer. Shadyside is wholly transformed into an outdoor gallery showcasing pieces from hundreds of artists. The Arts Festival offers something for everyone, and it’s a great, family-friendly event!
Pittsburgh Center for the Arts and Media is a contemporary and visual arts non-profit organization providing education to the community for over 50 years. They offer courses in almost every subject matter - from photography to ceramics and creative writing, there is a class for all interests and all levels. PCA&M provides camps, classes, and workshops and offers equipment and studio space rentals in addition to exhibitions held throughout the year.


There are several notable, high-achieving schools in the Shadyside neighborhood. A few schools include:
Shadyside Shadyside Shadyside
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Allison is passionate about relating to people, sharing her knowledge and creativity, and consulting with her clients through the process of buying or selling a home.