Photo: Rich McPeek

Morning

Let’s say you stayed the previous night in Carnegie, Green Tree, or somewhere generally not too far aware. This way you can start your day by taking a taxi through the Fort Pitt Tunnel and take in one of the best views of Pittsburgh when crossing the bridge immediately after. With Point State Park to your left and Downtown straight ahead, you’re going to want to take a right off the bridge and head towards Oakland.

Tell the driver to drop you off at the Golden Triangle Bike Rental on First Avenue. It’s a short walk from the road along a walking path. Rent a bike for the entire day [~$35]. Ride your bike west down First Avenue and take a right on Market St. This will take you straight to Market Square so you can pick up breakfast at anyone of a number of shops there including Prantl’s Bakery, Cherries Diner, or Einstein Bros. Bagels.

After you’ve filled up and enjoyed the relaxed atmosphere for Market Square, go east on Penn Avenue. You will pass several performing arts halls such as the Benedum and Heinz, but you’ll see those later. When you pass the Heinz History Museum you are officially in the Strip District. The morning is the best time to explore this neighborhood because it has a ton of fresh food markets, a fish market, and biscotti. The Strip is where you’ll find the local crafts. You can easily spend the rest of your morning here eating, talking, and shopping (if you’re still hungry, go to Pamela’s).

Noonish

Once midday hits, head back to Market Square and grab a sammich at Primanti Bros. At this point, you’re going to want to let all of this food settle in your stomach (assuming you’ve tried everything you saw in the Strip). You will want to go west on Liberty Avenue until you hit Point State Park. You can’t miss, if you do you will have ridden into either the Monongahela, Allegheny, or Ohio rivers, depending on which side you ride over in.

Afternoon

There’s three things you can do for a perfect afternoon in Pittsburgh.

Option 1: Go to a Pirates game on the North Shore.

The Pirates used to be the laughing stock of MLB. I grew up in Pittsburgh during their twenty year losing streak. That all changed in 2013 though when they had their first winning season (they didn’t win the World Series, but they did average over .500 as a team). Pirate games are fun for everyone, not just the sports-minded. The games are usually pretty family-interactive with giveaways, games, and the Pierogi Race. If you’re lucky PNC Park may even be having a fireworks night. It’s a great way to spend the afternoon, enjoying the weather and receiving another killer view of the Steel City.

Option 2: Chill in Point State Park and rent a kayak.

Point State Park is a great place to relax by Pittsburgh’s famed fountain, play Frisbee in the open grass, read a book, or to simply take a mid-afternoon nap in the sun. Whatever you choose to do at the park, there is a gorgeous 360-degree view of Pittsburgh and its surrounding neighborhoods. If you’re looking to be more active, Kayak Pittsburgh on the North Shore (right across the river from the park) rents kayaks on an hourly basis ($16-$25/hour). If you rent a kayak and float along the river just outside PNC Park during a Pirates game you might be lucky enough to catch a homerun as it whizzes out of the stadium.

Option 3: Skip the game and the park and go one of several nearby museums.

If sports and leisure are not what you need, there are a number of museums in the North Shore area that are easy to both bike and walk to. Near Heinz Field there is the Carnegie Science Museum & Highmark Sportsworks. Both are family friendly and more or less child-oriented. If you go north for a few minutes, you’ll hit the National Aviary and the Children’s Museum of Pittsburgh in the Allegheny Commons. If you’re looking more for art museums there is the Mattress Factory Museum which boasts contemporary art. There is also the Andy Warhol Museum, which, as the name suggests, honors the late Andy Warhol, a native Pittsburgher.

Evening

Your best bet for the evening is to move south from the North Shore to Station Square. Enjoy dinner at the Hard Rock Café or The Melting Pot. For yet another perfect view of Pittsburgh, shimmy on over to the Duquesne Incline at sunset where you will be greeted at the top by a unique aerial view of Pittsburgh and its surrounding neighborhoods. To finish the day off strong, take the incline back down, drop off the bikes by crossing the bridge, then walk back to Penn Avenue and catch a show at anyone of the following theaters in Pittsburgh’s Cultural District:
Byham Theater for dance, theater, and music
Benedum Center for ballet, theater, and opera
Heinz Hall for orchestra
Pittsburgh Public Theater for plays and musicals
Pittsburgh CLO for musicals
Arcade Comedy Theater for stand-up, improv, sketch comedy, and variety acts
Cabaret at Theater Square for live shows with dining

After the show, go to Meat and Potatoes for a hearty, late night, post-dinner meal before heading back to Carnegie, Green Tree, or wherever you came from.

The Extra Day

If you decide to spend an extra day in Pittsburgh (because you love it so much of course) head to Oakland and check out the Carnegie Museums of Art and Natural History as well as Phipps Conservatory. Even better head to the Pittsburgh Zoo and PPG Aquarium.

5 tips for 24 hours in Pittsburgh

1) Pittsburgh offers free WIFI for two hours anywhere downtown – use it wisely.
2) Pittsburghers are friendly, if you get lost don’t be afraid to ask for help.
3) Do not under any circumstances insult any of the sports teams.
4) For the best view of Pittsburgh, take the incline to the top of Mount Washington.
5) Learn the lingo! Also known as Pittsburghese.

Matador articles for Pittsburgh trip planning

How to piss off someone from Pittsburgh
15 reasons Pittsburgh is completely underrated
10 differences between people from Pittsburgh and everyone else
15 bars and restaurants Pittsburgh locals swear by
How to become a Pittsburgh in 20 easy steps

Getting around

Cabs: There are a number of taxi companies that service the Pittsburgh area. Uber does as well.
Public Transportation: Bus service between 4 am and 7 pm is free within the downtown area.
Local Transportation: If you’re feeling fancy or are traveling with a large group, several companies offer limousine & mini-bus services.
Bike PGH: Pittsburgh has an impressive network of biking paths lining all three rivers. To rent, prices range from $5-10 per hour or $20-45 for the whole day. If you book online though it comes with a discount.
Foot: Walking around town is pretty easy. The sidewalks are a decent size and everything is relatively close together. I would plan out what you want to do and see before heading out because Pittsburgh isn’t your typical grid-planned city. [Use this map of Pittsburgh]

Real Pittsburghers to Follow:

Pittsburgh Dad
Ya Jagoff!
Mikey and Big Bob

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