Things to do in Shadyside this Fall

Image courtesy of Pittsburgh Magazine

Shadyside is a centrally located Pittsburgh neighborhood that is filled with tree-lined streets, gorgeous homes, and a thriving business district. This neighborhood has a mix of large mansions and compact apartments for housing. It has a fun mix of residents. Artists, students, and young professionals all call Shadyside home. Each type of resident finds benefits to life in Shadyside. It's a very walkable neighborhood that has most things you’d need very close by. 

There are three main streets in Shadyside frequented for their shops and eateries. Walnut Street features popular chains like Apple, Banana Republic, and J. Crew. Ellsworth has a few small businesses owned by locals, and S. Highland has upscale furniture and design stores. Each of these streets is also lined with restaurants. There are small local restaurants and large chains on each street. When looking for things to do in Shadyside, you’ll be faced with lots of options. Here are some of the best things to do in Shadyside this fall!

Shadyside Shops

Shadyside has many shops within walking distance of each other. 

A colorful window display of books.
It will be exciting to open any gift bag to find all these colorful items. Image courtesy of Kards Unlimited

Kards Unlimited

5522 Walnut St | Shadyside |

This shop has been a fixture in Shadyside for over 50 years. It is a unique place that sells eclectic items. Plenty of the things you can find in here can be considered to be weird, but in very good ways. They have lots of books, some of which include gems like “dog shaming,” “I Could Pee on This. And Other Poems by Cats,” and “David Bowie Made Me Gay.” If you want to pick up a funny book, for yourself or for a friend, this is the perfect shop for it. 

They sell everything from mugs, to socks, and coloring books. Many of these items are covered in funny phrases. You can find various board games and so much more. You’ll have as much fun walking through this shop as you will have using what you’ve bought. 

A blue art piece on the wall above a white dresser with a small statue on top.
This art piece will add some character to any room. Image courtesy of Facebook


244 S Highland Ave | Shadyside |

Penhollows is a locally owned shop that sells furniture and books as well as other gift worthy items. They have been in Shadyside since 2007. The store offers uniquely designed furniture that will give you great design ideas for your own home. Their book offerings are a mix of common ones and rare ones that you won’t often find anywhere else. 

They sell kitchen supplies, stationary, and holiday décor as well as other items that can improve the image of your home. You can even purchase original art from reputable artists there. Penhollows is a great spot for buying gifts. If you want something exciting and different, this is where to shop for it. 

Shadyside Attractions

Shadyside has some outdoor locations it is worth it to pass through. 

A wooden street surrounded by brick row houses.
This is a street unlike any other in the country. Image courtesy of Pittsburgh Magazine

Roslyn Place

Shadyside is home to the only remaining wooden street in the country. It was built back in 1914 and has been there for over a century. There are very few wooden streets left in the entire world. The Pittsburgh History & Landmarks Foundation has designated Roslyn Place as a Historic Landmark. The street’s centennial was celebrated by city officials back in 2015. 

It is worth it to take a stroll up this street just to witness a relic of the past. It is always interesting to get a glimpse of how things were done in previous times. 

A yellow bridge with clear. decorative arches.
This bridge is a uniquely designed walkway that connects two neighborhoods. Image courtesy of Pittsburgh Art Places

Shady Liberty Pedestrian Bridge

This pedestrian bridge connects Shadyside to the East Liberty neighborhood. It is the first pedestrian bridge in this region that was designed by an artist. The bridge is filled with thousands of glass sequins that were created by the Pittsburgh Glass Center nearby. Parts taken from the 31st street bridge were used to construct this one. 

Shadyside Restaurants

Shadyside is filled with restaurants worth frequenting. 

Crispy noodles inside of a rich, golden broth.
This curry dish looks just as flavorful as it tastes. Image courtesy of PGH City Paper

This curry dish looks just as flavorful as it tastes. Image courtesy of PGH City Paper


242 S Highland Ave | Shadyside |

Noodlehead is a very popular Thai restaurant in Shadyside. They serve a wide variety of noodle dishes, from Pad Thai to Green Curry Linguine. It is also super affordable! Every noodle dish on the menu costs $10 or under. Despite the low prices, Noodlehead gives out large servings. You get to choose spice levels from 0-10 when you order your plate. This place also does BYOB. You can bring in any beverage you’d like to have with your meal. They also have non-alcoholic beverages on their menu. They offer soda, sparkling water, and hot tea. 

When visiting this restaurant, make sure to bring cash! Noodlehead does not accept digital transactions. Thankfully, they happen to have an ATM machine right on site!

Two chicken tacos topped with onions next to a glass of lime water and guacamole.
These tacos are piled with a great combination of toppings. Image courtesy of Good Food Pittsburgh

Tocayo Taqueria & Tequila

810 Ivy St | Shadyside |

Tocayo Taqueria & Tequila is an awesome restaurant in Shadyside that gets tons of rave reviews. It is an upscale establishment that serves nicely plated food that packs amazing flavors. They offer many of the things the average Mexican restaurant does, like burritos, quesadillas, and tacos. But it is a much different experience ordering these things from Tocaya. They also offer some unique food pairings that are not often found at similar restaurants. Aside from the regular chicken, steak, and fish tacos, they also offer beet, cauliflower & portabella, and octopus tacos. 

The dessert offerings are just as delicious as the food. They offer churros, lava cake, flan, and tres leche cake. Their drink menu also serves up some unique offerings. Some drinks like the “spicy watermelon” and “pepino” are made with Tajin chili powder, an ingredient not often found in drinks. 

Two people slicing into their own pizzas next to drinks and sides.
These pizzas have been baked to perfection. Image courtesy of Mercurio’s


5523 Walnut St | Shadyside |

Mercurio’s is a family-owned Italian eatery. It was founded in 1999. It has since been passed on from the original owners to their three children. In the beginning this place only made gelato, but has since expanded to include authentic Italian foods. Everything is also homemade, including their award winning gelato. 

At Mercurio’s, you can order pizza, antipasti, and paninis, along with beer, wine, and other drinks. Their gelato flavors include apple pie, dulce de leche, and pumpkin, along with many other great flavors. They even sell pizza dough balls so that you can take their dough home and bake it yourself!

Shadyside is a Pittsburgh neighborhood with a lot of character. It is scenic and walkable, something that keeps residents satisfied throughout their time there. Visitors also enjoy Shadyside for all it has to offer. The types of stores, restaurants, and attractions there leave something for anybody to enjoy.