City Guide: Shadyside

The tree-lined streets of Shadyside, the neighborhood many consider to be the jewel of the East End, have been home to a diverse population of Pittsburghers.

Since the late 1800’s, the residents of this neighborhood have represented everything from the working class to the uppermost reaches of society, including artists, activists, academics and professionals. Many of Shadyside’s ritzier streets are dotted with meticulously maintained Victorian homes with wide porches, while the landmark Millionaires Row of Fifth Avenue showcases historic mansions. Some of those have been converted to condominiums or luxury boutique hotels, including Sunnyledge at the corner of Fifth and Wilkins, or its neighbor across the street, the newly renovated Mansions on Fifth.

Shadyside and education have long been linked. Three of the best schools the city has to offer serve the area: Liberty School, a Pittsburgh Public School with classes for children in pre-K through fifth grade; The Ellis School, a private school for girls; and Winchester-Thurston, a co-ed private school. The Pittsburgh Center for the Arts holds exhibits, classes and camps for children and adults on a variety of visual arts. Chatham University, just over the Shadyside border in Squirrel Hill, boasts one of the nation’s oldest and most highly rated colleges for women as well as co-ed graduate courses.

For most, though, Shadyside means shopping. While the neighborhood is home to three business districts, each within walking distance of the others, Walnut Street is indisputably the heart of things. A tiny stretch, just a few short blocks from Ivy Street to Aiken Avenue, Walnut Street is home to some of the most desirable shops in the region, from eclectic independents to international powerhouses.

Shadyside has achieved a contented co-existence between beloved decades-old institutions, like Kards Unlimited, the Shadyside Variety Store, Schiller’s Pharmacy and Toadflax, and big-name retailers like Apple, American Apparel and United Colors of Benetton. Don’t miss the shopping gems tucked away just off Walnut, like Eureka! on Copeland Street.

Just a few blocks northeast of Walnut Street is Ellsworth Avenue, a distinctive blend of art galleries, antique shops, restaurants and niche retailers. Vintage clothing stores like Hey Betty! and Eons have clothed the retro hip for years, and Mendelson Gallery and Gallerie Chiz draw art lovers from miles away. Some of the city’s most loved restaurants are on Ellsworth, including Soba Lounge, Fajita Grill, Umi and Harris Grill.

Just a few blocks east of Ellsworth is South Highland Avenue, bordering on East Liberty. Restaurants are the highlight here as well, including a new Mad Mex, the always-popular Buffalo Blues, and the Mediterranean delight, Casbah. Oh Yeah! Ice Cream and Coffee, which was featured on the cover of Pittsburgh magazine’s July issue, is also here, as are antique shops and the legendary Smiley’s Pet Pad, offering some of Pittsburgh’s most personalized, expert shopping for pet supplies.

If you can shop, dine and stroll through Shadyside often, you’re lucky. If you get to call this neighborhood home, you’re luckier still.

Stand on the stars
Located in Shadyside at the corner of Fifth and Shady avenues is Pittsburgh’s Mellon Park. It may be small in comparison to other city parks, but it’s certainly striking nonetheless. A beautifully restored Gothic Walled Garden and water fountain can be found here, along with a dazzling must-see public art installation that transforms the garden floor into a celestial vision at night when 150 “stars” light up the ground. The park also offers a variety of free events throughout the year. A Fair in the Park, hosted by the Craftsmen’s Guild of Pittsburgh, takes place every September and includes live entertainment, activities for kids and, of course, plenty of art. The Bach, Beethoven and Brunch music series gives music lovers the opportunity to relax with a packed picnic basket full of their favorite bites while listening to live classical performances in the park. And if you’re more into music that makes you move, you can try your hips at a handful of free summer line-dancing lessons. Although Mellon Park contains modern amenities such as basketball courts, ball fields, tennis courts and playgrounds, it’s the classic yet extraordinary beauty within that makes this little park a big hit.

Romp around in the library
There’s no need to keep quiet in this library. As a matter of fact, playing, chatting, and jumping are highly encouraged. Managed as a volunteer run cooperative, the Pittsburgh Toy Lending Library is a safe indoor play space filled with a myriad of toys and activities for babies and young children through kindergarten age. Adults and babies under 1 are always free, and your first visit is free for the whole family. After that, it’s just $5 per child, up to a maximum of $10 per family. Memberships are also offered for as little as $25 per year, and reduced or free memberships are available based on financial need. There’s a little bit of everything for kids to play with, including infant toys, gross motor development toys, imaginative play toys and cognitive development toys. Those who choose to become members also have the privilege of “checking out” toys at no cost. Now how could the little ones not love this library?

Get dressed for less
Designer Days is a consignment store on Ellsworth Avenue that specializes in high-end clothing. Quality name brands like Louis Vuitton, Calvin Klein, Armani, Jimmy Choo and Versace fill the racks, and prices can be slashed by as much as 70 percent. Shoppers with expensive tastes and minimal budgets (or any savvy shopper for that matter) will feel like they’ve entered a fashion paradise. Those shopping for less expensive brands will likely find huge discounts at Designer Days’ sister store, Thriftique, in neighboring Swissvale. Ellsworth is also home to some great economical options for those searching out more eccentric vintage buys. You may need to do some hunting, but if vintage is your thing, you’ll surely be able to leave with some time-honored threads after spending an afternoon at Eons and Hey Betty.

Recoup from a wild night with half-off Bloody Mary specials
If you wake up on a Sunday morning (or afternoon) with a hankering for a Bloody Mary, we highly recommend you take a trip to Harris Grill. The special includes top shelf vodka options and the first drink is free if you order their killer $15 prix fixe brunch. Visit for more Sunday Bloody Mary Specials all over the city.

Stitch and bitch for free
Shadyside Stitch N’ Bitch meets at the Coffee Tree Roasters once a week, and they welcome any skill level. It’s free, but BYOK … bring your own knit-schtuff. Visit for more free knitting groups in Pittsburgh.

229 S. Highland Ave.

733 Copeland St.

Harris Grill
5747 Ellsworth Ave.

5847 Ellsworth Ave.

5849 Ellsworth Ave.

Caesar’s Designs
5417 Walnut St.

Henne Jewelers
5501 Walnut St.

5401 Walnut St.

Roberta Weissburg Leathers
5415 Walnut St.; 412/681-8188

324 S. Highland Ave.

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