A Drinking and Dining Guide to Pittsburgh’s Shadyside

Last Updated on April 1, 2021 by Jeremy

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Shadyside is one of those neighborhoods that we absolutely love. It is primarily residential but with a thriving business district (three, actually) that is heavily tilted to restaurants, bars, and coffee shops.

Great to live, great to visit, and home to many of our favorite spots in the city. As such, we thought we should share them in this neighborhood guide!

Shadyside History and Map

Roslyn Place in Shadyside

Up through the mid-1800s, Shadyside was primarily farmland. Around the time when Shadyside was annexed by the city, a train station opened which is said to have been named Shadyside due to its “shady lanes” (other sources, however, sometimes refer to the farms as being named Shadyside, too).

From there, a mix of industry and residences moved into the neighborhood. As the industry started to pull back away from the East End in the decades that followed, the residential side of the neighborhood grew.

Today, Shadyside is primarily residential with three distinct business districts- one on Walnut Street, one on S. Highland Avenue, and one on Ellsworth Avenue. While distinctly separate, they are all in close proximity for a short drive or a brief walk.

Shadyside is located in the geographic center of Pittsburgh and is fairly easy to define its borders. The neighborhood runs from Centre Avenue to the North (with a small cut-out at Baum on the west side), N. Neville Street to the West, Fifth Avenue to the South, and Penn Avenue to the East.

As Centre Avenue is a vibrant business district that borders East Liberty, many often lump the businesses on the Shadyside half of the street in with that neighborhood outright (we typically do as well). One of the biggest reasons for this is because the East Busway and a set of railroad tracks run just a block or so south of Centre and feels like a more definitive boundary than Centre Avenue.

As such, we often consider Centre to be the de facto northern border of Shadyside- especially when closer to the business district in East Liberty.

Attractions in Shadyside 

Roslyn Place

While we wouldn't say that Shadyside is particularly known for its attractions, there is one spot you really must see here- Roslyn Place just off of Ellsworth Avenue. The reason for this is that Roslyn Place is one of the last remaining wooden streets in the country and is a relatively unique sight that is practically hiding in plain sight.

To visit this one, we do not recommend driving into Roslyn Place as it is a dead-end road that is often tight for cars (also, it is a residential street so be courteous to those who live there). Instead, we recommend parking on Ellsworth and walking over to check this one out when you are in the neighborhood- it'll be a whole lot easier!

Restaurants in Shadyside

Mercurio's Shadyside

Looking for a new restaurant in Shadyside to try? Some of our favorites include the following:

  • Nak Wan Garden – A popular Korean restaurant with a large menu and massive portions.
  • Fujiya Ramen – A Japanese restaurant focusing on ramen and rice bowls.
  • Girasole – A critically acclaimed Italian restaurant often considered one of the best in the city.
  • Pamela's P&G Diner – A popular local breakfast chain known for their delicious hotcakes.
  • The Yard – A gastropub with a strong focus on grilled cheese sandwiches.
  • Mercurio's – Traditional wood-fired Italian pizza and homemade gelato. A taste of Italy.
  • Acorn – A modern American fine dining restaurant with a seasonal menu.
  • Cafe Moulin – French cafe serving crepes and other quick eats.
  • Soba – An Asian fusion restaurant by the Big Burrito restaurant group.
  • Con Alma – Modern American restaurant with live jazz music many nights of the week.
  • Mad Mex – Tex Mex fare with a twist from this chain from the Big Burrito restaurant group.
  • Casbah – A third restaurant from Big Burrito, all about higher-end Mediterranean fare.
  • Millie's  – An outpost for the popular local ice cream chain.
  • SubZero Ice Cream – An ice cream shop in Shadyside made with liquid nitrogen.
  • Noodlehead – Thai street food restaurant with delicious noodles and amazing prices.

Bars in Shadyside

While the bar scene in Shadyside is small, there are a few you may be interested in:

  • Cappy's – A modest pub and bar in Shadyside.
  • Urban Tap – A modern bar known for having over 100 beers on draft.

Coffee in Shadyside

Adda Coffee Shadyside

Shadyside has several coffee shops including chains and locally owned spots. A few local favorites include the following:

  • Adda – A relaxing and welcoming coffee shop steps from East Liberty.
  • Arriviste – A specialty coffee shop that makes exceptional pour-overs and espresso.

Parking in Shadyside

For the most part, the main business districts of Shadyside offer metered street parking on the main roads and permit parking on side streets with limited duration free for non-permit holders (be sure to check the signs).

The one exception to this would be the Walnut Street business district which has a paid parking garage located on Bellefonte Street just behind The Yard restaurant. As parking here can be somewhat limited, if you are visiting this section of Shadyside especially, it may make the most sense to head to the garage and save yourself a few loops around the neighborhood.

Hotels in Shadyside

The only hotel located within Shadyside proper is the luxury hotel Mansions on Fifth.

There are many other hotels right at the neighborhood boundary including the Courtyard by Marriott Shadyside and Hyatt House Pittsburgh (both technically in Bloomfield) plus the SpringHill Suites by Marriott in Bakery Square (Larimer/East Liberty). These would all be within a brief walking distance of the main business districts in Shadyside. 

From there, a few apartments are also available to rent on sites like VRBO as well to enjoy the heart of this residential neighborhood.

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