How To Spend a Perfect Day on the Northside of Pittsburgh

Originally published October 1st, 2016.

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Something great about Pittsburgh: every neighborhood is so similar, so different, and and so unique... all at the same time. The North Side of Pittsburgh is no exception. 

The North Side is the area in Pittsburgh north of the city (shocking, I know).  It's full of brick streets, victorian homes, and a vibrant personality. 

Some businesses and restaurants have been in the area for decades.  However, word has spread of the area's elegant homes and eager newcomers have shuffled into the vacant storefronts. 


Regardless of the politics, the area has blossomed into a happening space.  It's starting to gain confidence and show off its natural beauty. An entire day can be spent in the North Side, complete with culture, food, and exercise.


10:00AM: Pear and the Pickle - Start the day with breakfast and coffee at the Pear and the Pickle on the Troy Hill.  To make this experience complete, you must ascend Troy Hill via the rollercoaster that is Rialto Street.  Why? You will understand once you see it.  Enjoy Stumptown coffee and split a breakfast sandwich with your companion (or yourself).  Although their deli sandwiches are hearty and feature Boars Head meat, the Pear and the Pickle shows what they really can do with their breakfast sandwiches - Mancini bread, fried eggs, fresh sausage, enough said. Read the paper, or a book, and enjoy a leisurely morning in the picturesque deli/grocer. 


11:30AM: Take a drive across Pittview Avenue to where it meets Logan Street. Pittview Ave has the best view of the northeastern shores of the Allegheny River and the surrounding neighborhoods. This is my favorite view of the entire city.

12:00PM: Mattress Factory Museum - The experimental contemporary art museum, the Mattress Factory, has been captivating Pittsburgh since 1977 with its provoking pieces and ever-changing collection.  Even if it was just for the two Kusama installations, the Mattress Factory is worth the trip. Luckily, there is plenty more to feast your eyes (and mind) on. 


1:30PM: Randyland - A short (but beautiful) walk from the Mattress Factory is Randyland - "Pittsburgh's most colorful landmark."  Randyland is the ongoing repurposing art project that Randy Gilson has been creating on the Northside since 1995 (although he was transforming the neighborhood even before that).  Read my piece on Randyland here!
Randyland Website.


2:00PM: LUNCH: There are many great places in the area to grub down.  Here are 3 suggestions:

Nicky's Thai Kitchen - Open until 3pm for lunch, Nicky's Thai Kitchen has been cooking up some of the city's favorite Thai food for years.  If weather is nice, the patio is a must. 

James Street Gastropub and Speakeasy - Open from 11AM to 1am.  James Street Gastropub and Speakeasy serves a solid pub lunch and dinner with a few twists. Get more information on their website.

Legends of the North Shore - Open 11:00AM -9:00PM.  This place is a legend in Pittsburgh, and has been since its opening in 2002.  At Legends of the North Shore, the lunch or dinner menus are expansive, and the food is satisfying . I would describe it as Americana meets booze.   More than anything, the place is very homey.


3:30PM: Around this time you're going to need a drink.  Head to Allegheny City Brewing or Penn Brewery.

4:15PM: Rent Bike - The Northside has a very central public bike rack as part of Pittsburgh's wonderful bike rental system, Healthy Ride.  The streets of the Northside are beautiful, wide, and simple to navigate.  If the weather allows, stop by the station on the North Side to get a bike. Biking is the best way to see the area, so take advantage of this opportunity.   Be sure to see the Mexican War Streets and Western Ave. $4 an hour per bike. 

4:30PM: Bike/Walk past the City of Asylum: Pittsburgh's home and workspace for exiled writers from all over the world.  Check out my post on it in the Eat This Poem Pittsburgh guide


5:30PM: Bike/walk to the Allegheny City Market - If you are looking for a sinful way to end your day, stop by the Allegheny City Market for many local treats and snacks, including my all time favorite frozen cookie in Pittsburgh, Leona's Ice Cream Sandwiches.

6:00PM: Appreciate your wonderful day in Pittsburgh. 


The Children's Museum of Pittsburgh
Great place for kids - I love it as an adult. 

The National Aviary
A must for bird lovers living or visiting Pittsburgh. 

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