Pittsburgh Weekend Guide – First Timer Edition

Posted By Jeremy in Explore


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If there is one thing I hate more than poorly thought out city guides, it would be poorly thought out city guides that feature ridiculous suggestions that no one would actually do. Are you really going to drop $200 for that spa treatment, head out of town to an obscure restaurant, or go to a specialty museum on your first visit to a city?

Probably not.

In fact, you likely wouldn't do it on your second, third, or fourth visit either (although if we had our way, you may work in an obscure museum because Pittsburgh has some pretty awesome ones).

Our first-timer's weekend in Pittsburgh guide gives a good introduction to the city and is oriented for someone who has never been here before.

This list has been crafted from years of experience in showing friends and family around town while incorporating many of the city's highlights, skipping some of the common letdowns, and overall giving you a welcome that will make you want to return to this great American city many times in the future.

Friday Evening – Arrive and Visit Mount Washington

Duquesne Incline and Pittsburgh's Skyline

Arriving into Pittsburgh on Friday evening can be hit or miss as our roads can be, for lack of a better term, congested.

If you come in from the South or West, you will travel through the iconic Fort Pitt tunnel, but if you arrive during rush hour your entry may be slow thanks to the commuter traffic (and if you're coming from the North or East, traffic will slow the closer you get to downtown but will likely not be as bad).

Whatever you do, don't hold it against us as we promise things will get better.

Duquesne Incline in Pittsburgh

To start your weekend in Pittsburgh, you'll probably want to take some time to freshen up at your hotel and grab dinner at a nearby restaurant (see our recommendations list at the end of this article depending on your Pittsburgh neighborhood of interest).  

Once you're relaxed, try to force yourself away from the hotel and head to the Duquesne Incline for a sunset or night-time view of the city.

Point of View Statue in Pittsburgh

This iconic funicular is one of two remaining in the city and has been in operation for over 100 years. At the top you can check out the museum dedicated to the incline's history and take in the iconic view of Pittsburgh on the viewing platform.

Be sure to head out of the station and up the hill roughly 500 feet to your right to check out the Point of View statue and an even better angle of the city that most visitors do not go to!

  • If you're looking for a romantic restaurant during your visit, make advance reservations for Monterey Bay Fish Grotto, located just across the road from the Point of View statue.  It is home to one of the best views in the city and great food too!

Saturday Morning at the Strip District

Smelling Peppers at Reyna's

Our favorite Saturday morning begins with a trip to the Strip District just outside of downtown. This neighborhood has seen a lot over the years from industrial work, to warehouses, and is now home to one of Pittsburgh's largest international market districts.

Cheeses at Penn Mac in the Strip District

Hop around international grocery stores like Lotus Noodle (Asian), Labad's (Middle Eastern), Reyna's (Mexican), Wholey's (seafood and meat), and the Pennsylvania Macaroni Company (Italian) for some of our favorite international offerings in addition to an incredible array of boutique shops. (For a full list of cool places, check out our Strip District guide!)

Chori Pan from Gaucho Parrilla in the Strip District

While in the Strip District be sure to stop at Wigle Whiskey for a sampling of some of the most awarded spirits in the country, and, come lunch time, try out either Kaya (Caribbean), Smallman Galley (a unique food hall concept), or Gaucho Parrilla (Argentinian)- three of the best restaurants in the city.  

Just plan to visit both on the earlier side as the crowds come to these one early on in the day!

  • An alternative restaurant choice popular with many first timers is Primanti Brothers, the local sandwich chain famous for making fries on a sandwich a delicacy.  We may not personally recommend this as an option, but if you must visit the chain during your stay, the original location in the Strip District is the one you must visit as the others simply do not compare. Just be sure to add a fried egg on to whatever your order- trust us on this one!

Saturday Afternoon Based on Your Interests

Bicycle Heaven in the North Side

For Saturday afternoons and evenings, there are a number of great options available in the city.  Based on your interests, we'd like to make several varied recommendations and let you decide based on your mood, the weather, and your itinerary as a whole.  A few great options include:

  • For the sports lover, everyone knows about the Pittsburgh Steelers, Pirates, and Penguins– and if you're lucky enough to visit during a Saturday afternoon game, you can't go wrong by taking one in.  We want to give a special shout-out to the Pirates here, as PNC Park has one of the most beautiful views of the city you can find.
  • For the lover of the off-beat, head over to the North Side to check out the famous Randyland– Pittsburgh's most colorful spot, as well as the largest bicycle collection in the USA, Bicycle Heaven (both free).  If you find yourself with a few more hours to spare, the Mattress Factory and Andy Warhol art museums are nearby and very interesting too (both with paid tickets)!
  • For the outdoor enthusiast, take a bike ride along the North Shore bike trail, home to some incredible views of the city and stadiums.  If you have time, be sure to cross one of the many gorgeous bridges and make the short ride over to the Point, too!
  • For the local history buff, you most certainly want to head downtown to check out the Fort Pitt Museum and Point State Park, where Pittsburgh's early history comes alive.  After, make your way back to the Strip District to check out the Heinz History Museum, which continues the city's history all the way to today.  (We recommend visiting the Fort Pitt Museum first as your ticket gives a discount to the Heinz History center on the same day, but a reverse visit has no special discount.)

As these activities will take up most of your day, and are spread out over the city, odds are good you'll want to head back to your hotel to relax for a bit before heading out to dinner or for a quick drink before calling it a night (check out some of our recommendations at the end of this post for a few suggestions).

Sunday in Oakland and Squirrel Hill Before Departing

Phipps Conservatory in Oakland

Sundays in Pittsburgh are hit-or-miss depending on what you are interested in as many businesses are closed or maintain odd hours, so you'll do well in planning the activities for the day ahead of time (our Sundays in Pittsburgh guide is available here to give you a good place to start).

One neighborhood that is bustling on Sundays is Oakland thanks to its numerous universities including Pitt and Carnegie Mellon.

The star attraction of this neighborhood is Phipps Conservatory, a 120+ year old botanical garden that is among the best we've ever visited.

These gardens feature seasonal flower shows and include over a dozen themed rooms from the Fruit and Spice Room to the Orchid Room (two of our favorites).

Pitt Panther and the Cathedral of Learning

After exploring Phipps, be sure to stop inside the University of Pittsburgh's Cathedral of Learning located just a few blocks away for a quick peak at one of the most beautiful (and tallest) university buildings in the country.

  • The Cathedral of Learning also offers a self-guided tour of Pitt's Nationality Rooms which are designed to look like classrooms from around the world in different time periods. Most of the time the rooms on the upper floor are free to view without the tour too as long as class is not in session!

Soup Dumplings at Everyday Noodles in Squirrel Hill

We recommend taking the short drive over to Squirrel Hill for lunch as this neighborhood is quickly becoming a hub of Asian cuisine with offerings from Chinese to Taiwanese, Malaysian to Japanese, and everything in between.

There are so many restaurants that it is a bit hard to decide where to visit, but we recommend a stop at Everyday Noodles to try their famous pork soup dumplings and house-made Taiwanese noodle dishes. After, if you're still hungry, make a brief stop to Razzy Fresh to try the city's best frozen yogurt as well!

  • Both Squirrel Hill and Oakland are also home to a great breakfast restaurant, Pamelas P&G Diner, which is home to some of the best pancakes in the city.  Be warned that the wait in the morning can be quite long as they do not take reservations and are a Pittsburgh institution, so this one would be a great early lunch alternative if you're looking for something different or are getting a late start!

Hotel and Restaurant Recommendations

Renaissance Hotel in Downtown Pittsburgh

Pittsburgh is home to several notable hotels that you may be interested in staying at during your stay, including:

  • Sheraton Station Square is located in the South Side, just across the river from downtown.  This hotel is located within walking distance of the second funicular Pittsburgh has to offer, the Monongahela Incline, and is located near many restaurants and bars in the South Side neighborhood (driving may be required).
  • Quality Inn University is a more budget friendly hotel located close to the universities in Oakland.  Although the hotel is not within walking distance of most of the attractions or restaurants, it is within a short driving distance to favorites in Squirrel Hill such as Everyday Noodles.
  • Wyndham Grand and Renaissance Pittsburgh are two premium hotels located right in the heart of downtown Pittsburgh.  These hotels are within walking distance of gourmet restaurants including tako (and their great tequila bar), Butcher and the Rye (and their great whiskey bar), and many more.  Just be sure to make a reservation for these restaurants over a week in advance as these book up fast!

For more great restaurants in the above mentioned neighborhoods, check out our Pittsburgh city map!

Or, if you are looking for more hotel recommendations, check out our Pittsburgh hotels review directory which features every hotel we've stayed at in the city!

When it comes down to it, this weekend guide is only starting to scratch the surface of all of the best things Pittsburgh has to offer.  One of the things we love most about this city is that there is always something fun to do, and to truly see it all you'll have to return to visit many times in the future.

If you follow our advice and check out the attractions and restaurants featured in this guide on your first visit, we're certain you'll fall in love with this city just like we did and will do everything in your power to return again in the future.

Looking for more things to do in Pittsburgh? Check out 156 of the best sights and attractions at the previous link!

Have a recommendation to add for first time visitors to Pittsburgh? Comment below to share!

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14 Comments

  1. You missed Shadyside where there are over 30 independently owned boutiques and also a visit to Prantl’s for the burnt almond torte.

    Post a Reply
    • I wouldn’t say I missed it. Shadyside just isn’t what I’d put in a first timer’s guide to the city. Aside from the high-end shopping (and Prantl’s), I don’t think it is a must see- especially on a first visit.

      Post a Reply
  2. This list is spot on! Even a couple things I didn’t know about, like bicycle heaven! I would add morning glory inn bed and breakfast under lodging. It’s right on southside, so great for late night fun!

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  3. If you’re in Oakland, Dave and Andy’s is a must-visit! They’re open year-round (I believe in Sunday’s, too) and have the best ice cream cones. Period.

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    • I remember growing up in PGH and going to the factory for ice cream called Islay’s. I moved away 36 yrs ago and unfortunately there was nothing there. Now I want to go back. I hear there’s so much to do and see.

      .

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      • Isaly’s was soooo Pittsburgh …..from its unique ” skyscraper ” cone modelled after the Cathedral of Learning … the big ice cream factory built right in Oakland … to the invention of the ” Klondike ” bar … decades before any other dairy.
        Public school and Parochial school students got annual tours of the ice cream plants and everyone got a free Klondike ( to drip and spill all over ). Great Pittsburgh memories.
        I would give a limb (!) for a half gallon of its unique ( based on expensive white chocolate base )….” Isaly’s Chocolate Chip “.
        Nothing like it anywhere. <3

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    • There’s also the Original Hot Dog Shop in Oakland.

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      • I remember Weiner World in the 1960’s and hotdogs from Grants…and burgers from the Brass Rail….and corned beef sandwiches from Robert’s on Liberty Ave….the Good Ole Days!

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  4. If you listed, I missed them. Any really good Sunday brunches in Pgh, other than the one everyone knows about at the Grand Concourse?

    Post a Reply
    • Brunch is hit or miss in Pittsburgh in its true intent, but it does give us a good idea for an article in the future. There aren’t many that are as famous as the Grand Concourse, but I think the brunch at Eleven, Kaya, and Smallman Galley in the Strip are all worth noting as options we enjoy!

      Post a Reply
    • There are lots of new brunch locations in the city. One of our favorites is proper brick oven and pub house in the old tambellinini building near the Benedum.

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  5. I live in nc but my home will always be Pittsburgh. I miss Saturday movies Sunday jazz Local musicians @Melon,Schenley, Highland, Point, North SIde, Parks of PA. FREE! All summer long

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    • Brunch at the Rivers Casino is a good pick. Budget friendly, and you can sit outside on the river and take in the beautiful view. Only drawback is you must be 21yo. Great article for first timers!

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  6. I’ve recently waxed nostalgic remembering (vaguely) visits to my mother’s brother’s family in Troy Hill. I now live near San Francisco and chuckled when I read Pittsburgh is the poor man’s San Francisco!

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