Our home sweet home. Pittsburgh feels caught between eras, with the steel industry’s legacy contrasting the city of bridge’s growing tech presence. And yet, Pittsburgh’s rich history pairs wonderfully with this injection of innovation to create a distinct, proud culture. Travel like a local to fully appreciate this amazing city.
Quite frankly, we have too many recommendations to possibly fit into a single weekend. Rather than overwhelm you with options, we put together our ideal two-day itinerary for a Pittsburgh getaway. If you’re planning to spend longer in the city or you want to swap out a few recommendations, we also included more detailed lists of restaurants, cultural activities, and day trips towards the end of this post. Hope yinz enjoy!
Two-Day Itinerary
Everyone has different travel styles and preferences, so there is no such thing as a one-size-fits-all itinerary. And that’s okay! Our differences keep the world interesting and make travel exciting. In an effort to accommodate as many styles as possible, we aimed to include a mix of activities and price points in our recommended itinerary. If something seems outside your budget or doesn’t appeal to you at all, just refer to the additional sections towards the bottom of this post for more options! Without further ado…
Day 1
| Breakfast | 350° Bakery |
| Morning Activity | Mount Washington and West End Overlook Park |
| Lunch | Gaucho Parrilla Argentina |
| Afternoon Activity | Senator John Heinz History Center |
| Dinner | Primanti Bros. Restaurant & Bar |
| Evening Activity | Night out in Lawrenceville (or live sporting event) |
This day contains a mix of classic Pittsburgh attractions and local favorites!
Start your day in the Southside Slopes to visit 350° Bakery. This small, counter-service spot isn’t much to look at from the outside, but it has legitimately some of the best biscuit sandwiches we’ve ever had. They are big, fluffy, flavorful, and just perfect in every way. If your stomach has room leftover after the sandwich, two things:
- We’re impressed
- Treat yourself to a breakfast pastry
Every pastry we’ve had at 350° Bakery has been great, but our favorite has to be the chocolate babka. Like the biscuit sandwich, it is pretty sizeable, so you’re not alone if you decide to save half of it for an afternoon snack.
After you finish your breakfast, it is only a short (~7 minutes) drive to the Grandview Overlook on Mount Washington. Without question, Mount Washington offers the most famous view of Pittsburgh, as you get to see the Ohio, Allegheny, and Monongahela Rivers come together to frame the city’s skyline and downtown’s Point State Park.
While a lot of people would recommend taking the Monongahela Incline to the top of Mount Washington, we don’t think it is worth it. The ride itself is nothing special, and you can drive to the exact same viewpoint. Rather than spend your time waiting in line or riding the slow cable car, we suggest you pay a visit to the West End Overlook Park. It is just another 10 minutes from Grandview Overlook by car, and it offers more spectacular views along with a grassy area where you can relax and appreciate the scenery.
Take your time digesting breakfast at the park; the next stop is lunch. It’s a good lunch too. Gaucho Parilla Argentina may just be our favorite restaurant in the entire city.
At Gaucho you’ll find some of the best Argentinian food north of the equator. All of the meats are incredible, and the complimentary chimichurri sauces are out of this world. You really can’t go wrong with any of the steak plates or sandwiches, so we recommend just choosing your favorite cut. For us, that’s either the ribeye or skirt.
While Gaucho is also open for dinner, its reputation leads to extremely long waits. If you’re visiting Pittsburgh on a weekend, your best bet is to visit during off hours. Otherwise, you may be in a line out the door for up to hour. Lunch tends to be less busy than dinner, so we’d highly recommend visiting this counter-service restaurant earlier in the day. You could also get takeout to skip the line, but please – we beg you – make sure you get plenty of each type of chimichurri to-go if you do.
After lunch, it’s time to take in some of the city’s culture. While Pittsburgh has a ton of museums worth visiting, we think the Senator John Heinz History Center is the best pick for a first time visitor. At less than a mile from Gaucho, it is also a convenient next stop.
As a Smithsonian affiliate, the Heinz History Center has an exhibit for everyone. If you consider yourself a history buff, treat yourself to the Lewis & Clark exhibit and the From Slavery to Freedom exhibit that tracks from 18th century Africa to present-day Western Pennsylvania. If you love sports, be sure to check out the embedded Western Pennsylvania Sports Museum that serves as a tribute to Pittsburgh’s avid sports culture. And if you love ketchup, you can’t miss the Heinz exhibit.
It’s worth noting that some exhibits at this museum rotate, so check out the official website before going so you can plan your visit. You’ll want to spend at least a few hours at the Heinz History Center to make the most of it!
It’s a good thing you’re spending so much time walking through the museum, because dinner is another heavy meal. Pittsburgh doesn’t really do light.
Even though it’s not one of our favorite restaurants in the city, it’s hard to put together a Pittsburgh itinerary that doesn’t include the classic Primanti Bros. If there is one dish that is nationally attributed to Pittsburgh, it’s a sandwich filled with french fries and coleslaw, and Joe Primanti is credited with inventing this heart-stopping creation.
There are a lot of Primanti locations around the city now, but you should visit the original in the Strip District to cross it off the Pittsburgh bucket list. As far as food is concerned, our favorite sandwiches are the double egg & cheese and the sirloin steak & cheese. No sides needed since – again – the fries and slaw are on the sandwich.
Primanti’s is also a great place to start your night because it doubles as a decent bar with cheap drink specials. (They proudly say that the Pitts-burger is their #2 best seller … because beer is #1). Enjoy your trip and have a couple!
After you’re done at Primanti’s, you have some options. If the opportunity presents itself, you should absolutely attend a live sporting event while in the city. More than any United States city we’ve visited, Pittsburgh lives and breathes sports. There is so much history with the city’s teams, and you’d be hard pressed to find a bar around the city that doesn’t have a TV and memorabilia lining the walls. Obviously sports are seasonal, so you may not have this option, but do yourself a favor and look into it in advance. Steelers and Penguins games in particular are nuts and especially fun.
If going to a game isn’t an option or isn’t your thing, you should make your way to Lawrenceville. This hipster neighborhood has a ton of nightlife options, ranging from bowling to bars to clubs. Our favorite spots here are Arsenal Bowl, which is a great bowling alley with serious vintage vibes (think red carpet walls and dim lighting), and Walter’s, which has an awesome dog-friendly patio bar with lawn games. Back in 2013 Pittsburgh ranked as having the most bars per capita in the United States, so you should try to go out at least one night while in town.
That’s it for a busy Day 1! You can read our recommendations on where to stay and how to get around at the bottom of this post.
Day 2
| Morning Activity | Strip District |
| Brunch | Pamela’s Diner |
| Afternoon Activity | Point State Park |
| Supper | Butcher and the Rye |
| Evening Activity | Sunset viewing in the North Shore |
After a late night out in Lawrenceville, you likely won’t want a super early start on Day 2. Sleep in a bit and start your mid-morning in the Strip District. This historic Pittsburgh neighborhood is lined with boutique shops and has street vendors outside most weekend days, so it’s a great place to walk around, buy some souvenirs, and try some Pittsburgh staples. We can’t help but get an atomic pepperoni roll from Jimmy & Nino Sunseri Co. every time we’re there.
Also in the Strip District is Pamela’s Diner, one of the most famous breakfast spots in the city. The pancakes and Morning After Special here are incredible. You’ll likely encounter a wait around brunch time, so we recommend putting your name down for a table and then heading back to the shops for a bit.
After brunch, it’s time to check out another one of Pittsburgh’s great parks. This one will look familiar, as it’s the same park you saw from above when visiting Mount Washington.
Point State Park is aptly named, as it sits at the intersecting point of the three aforementioned rivers. The fountain here is an iconic Pittsburgh landmark and spouts to 150 feet! There is a large grassy area adjacent to the fountain as well as a large sitting area around the water’s edge, so you’ll have plenty of room to space out. We love packing a few drinks and hanging out with friends here, and you could even kayak through the rivers surrounding the park by getting a rental from Kayak Pittsburgh North Shore.
This state park is also home to the Fort Pitt Museum, which is technically part of the Heinz History Center and details the history of our great city. Just in case the infamous Pittsburgh turns ugly, it’s nice having the indoor museum as an escape.
Since you’ve only had one meal to this point in Day 2, we recommend grabbing an early dinner at Butcher and the Rye. This is, without a doubt, our favorite upscale restaurant in Pittsburgh. Make a reservation in advance, sit back, and eat to your heart’s content. While everything here is delicious, we strongly suggest that you get the Sunday Gravy and a bourbon cocktail with whatever main course you choose.
Having an early dinner will set you up perfectly for a beautiful Pittsburgh sunset. In our opinion, there’s no better place to take in this view than the North Shore. We recommend making your way to the Mr. Rogers Memorial in this area to relax, snap some photos, and pay your respects to the timeless Pittsburgh neighbor. While you’re over there, you can also walk along the river and get an exterior view of the famous Heinz Field. There’s no better way to end your time in Pittsburgh.
Where to Eat
In our two-day itinerary, we talked in depth about Gaucho Parrilla Argentina, Butcher and the Rye, Pamela’s Diner, 350° Bakery, and Primanti Bros. Restaurant & Bar. If you’re in the mood for something different, here are some of our other favorite restaurants from around the city!
- Oakmont Bakery (Oakmont): While it’s a bit outside the city, Oakmont is THE place to get dessert around Pittsburgh. Their selection is honestly overwhelming. The New York-style bakery uses a ticket system to move through the line out the door, so you better use the wait to browse the options and make up your mind. You’ll need all the time you can get. Everything is delicious, but our favorite options are the Oakmonter cake (mix of cheesecake and chocolate fudge cake), thumbprint cookies, and doughnuts.
- Iron Born Pizza (Millvale): This Detroit-style pizza eatery got its start in Smallman Galley, which is a launchpad for new restaurant concepts. It didn’t take long for the popular spot to graduate to its own standalone restaurant. Their menu includes some really unique pizzas that all use fresh, high quality ingredients. We wouldn’t say this is the spot to get a traditional slice, but it’s some of the best pizza in the city and offers great, interesting flavor combinations.
- Wild Rosemary (Upper St. Clair): This small, upscale restaurant feels like home. Because of Wild Rosemary’s size, you may need to make a reservation months in advance to get the date and time you want. Once you take care of the logistics, though, you’re in for a treat. Wild Rosemary has very friendly service, spectacular food, and it’s BYOB. We highly recommend it for a special occasion. Their menu changes frequently, but everything we have tried has been delicious.
- DiAnoia’s Eatery (Strip District): This wildly popular Italian spot is a great option for both brunch and dinner. Everything is homemade, and you’ll love their signature meatballs and red sauce. Be warned though – you’ll be out of commission for the night after this meal.
- Dish Osteria (Southside Flats): Another awesome Italian option – because Pittsburgh – that comes with a cozy, intimate setting. It’s literally in a converted row house, so you’ll feel like your eating in the family’s dining room. The food is also incredible. We especially loved the scallops, gnocchi, and saffron risotto.
- Industry Public House (Lawrenceville): We’re here for the pretzels. Yes, Industry Public House has a wide selection of great pub fare, but let’s be honest. The pretzels are what keep us coming back. Each one is about the size of our two heads put together, and they are spectacular. This is also a great place to watch the game or grab a drink before a night out!
What to Do
We covered a lot of activities in our two-day itinerary (see above for details on Mount Washington, the West End Overlook Park, the Senator John Heinz History Museum, Lawrenceville nightlife, Pittsburgh sporting events, the Strip District, Point State Park, and sunset from the North Shore). And yet, Pittsburgh has even more to offer.
- Local Breweries: There are a ton of great breweries around the city that are perfect for an afternoon outing. Grist House may be our favorite, with its large outdoor patio and delicious beers. Some of the other more popular breweries that we’d recommend are Penn Brewery (Troy Hill), Church Brew Works (Lawrenceville), Eleventh Hour Brewing (Lawrenceville), and Brew Gentlemen (Braddock). Even though we personally aren’t the biggest fans of the beer at Church Brew Works, the atmosphere in itself makes it worth a visit.
- Southside Nightlife: This suggestion is not for the faint of heart. Come weekend nights, Pittsburgh’s many college students and post-grads descend upon Southside looking for a good time, and there’s really no better place to find it. The iconic Carson Street is essentially a straight mile of bars, clubs, and restaurants. You need to be in the right state of mind to make the most of a night out in Southside. Luckily, there’s a spot for every mood. Jimmy D’s is a popular spot for dancing, Mario’s is an iconic Pittsburgh bar with a shot wheel, and Acacia is a speakeasy with a laid back vibe and great cocktails.
- Andy Warhol Museum: Pittsburgh’s museums include more than just the Heinz History Center. The Andy Warhol Museum may be the city’s most iconic art museum, as it contains different types of work from the many eras of the artist’s career. It also has an entire floor dedicated to a rotating exhibit of other artists. If you’re in the mood for even more museums, we’ve heard great things about The Mattress Factory. While we haven’t visited this contemporary art museum, it is near the top of our to do list.
- McConnells Mill State Park: If you’re in Pittsburgh long enough to want to get out of the city, we definitely recommend a day trip to this state park! McConnells Mill has some good hiking options, and you may even see some kayakers dropping into the river. A bit further from Pittsburgh is Ohiopyle State Park, which also has a number of hikes, an awesome waterfall, and even offers whitewater rafting. If we had to choose between McConnells Mill and Ohiopyle, we’d likely pick Ohiopyle. It’s well worth the extra half hour drive each way if you have time!
Where to Stay
One thing we love about Pittsburgh is that every neighborhood is a little bit different. There’s truly something for everyone. Depending on your personality and what you plan to do in the city, the right place to stay for you will vary. To help you decide, we’ve provided some commentary on a few of Pittsburgh’s more tourist-friendly neighborhoods below.
- Strip District: For the two-day itinerary we detailed above, we would recommend staying in the Strip District. It is a good, central location that provides easy access to Pittsburgh’s other neighborhoods while offering plenty of restaurants and attractions of its own. You’ll love the area’s mix of history and modern comforts. The only thing we’d say the Strip truly lacks is nightlife variety, as there isn’t a ton to do after dark aside from Cavo Night Club.
- Lawrenceville: This neighborhood adjacent to the Strip District is another great place to stay. Lawrenceville has an awesome collection of shops, bars, and restaurants, so it is very pedestrian-friendly and conducive to going out. This neighborhood is rightfully considered Pittsburgh’s premier hipster area (see: TripAdvisor’s list of the coolest hipster neighborhoods in the United States in 2018). Lawrenceville’s only downsides compared to the Strip District are a lack of hotels and the fact that it is slightly further from many of Pittsburgh’s main attractions. Luckily, there are plenty of Airbnb options in the area.
- Shadyside: For a more laid back visit to Pittsburgh, Shadyside is a great option. This upscale neighborhood is one of the nicest in the city, and it is conveniently located next to Carnegie Mellon University’s campus. There are plenty of shopping options, restaurants, and bars in the neighborhood, along with some truly massive, historic homes that you can admire from the road. It’s a bit farther from the city’s main attractions, though, and we’d argue that the best restaurants and nightlife are elsewhere.
- Southside Flats: Southside is an incredibly walkable neighborhood that has everything you can want in a home base … with the exception of peace and quiet on a weekend night. As mentioned above, it is an incredibly popular spot with college students and post-grads looking to bar hop on Fridays and Saturdays. The trade-off, though, is that Southside has some great restaurants, and you’ll be able to easily walk to the bars if you’re interested in joining the crowds for a night out.
- Downtown: Unless you’re coming to Pittsburgh for business, there’s no reason to stay downtown. Yes, there are some good restaurants and Point State Park there, but we’d recommend staying elsewhere and instead commuting to those places. Both the Strip District and Southside are plenty close to downtown.
Other Tips & Tricks
- Getting Around: The bus system is Pittsburgh is actually pretty solid. If you can get from Point A to Point B easily on the bus, we definitely recommend going that route to save some money and avoid searching for parking. Check out the Port Authority’s website to see if there’s a route and timing that would work for you! There’s also a Pittsburgh Port Authority Bus Tracker app that we find really helpful. If you don’t want to take the bus, driving or taking a rideshare are always options. Finding street parking usually isn’t too difficult.
- Weather: Depending on the season, Pittsburgh can get very rainy and/or very cold. You’ll want to check the forecast before your trip to pack appropriately. It also never hurts to bring a rain jacket and boots to the city.
- Traditional Pittsburgh Foods: While we mentioned the fry-filled sandwiches at Primanti Bros., we didn’t highlight some of Pittsburgh’s other specialty dishes. Locals love their pierogis, pepperoni rolls, and Pittsburgh salads, so you should try some while in the city! In case you were wondering, a Pittsburgh salad is just a salad covered with french fries.
Happy traveling!
Kitrina & Jordan (& Arya)
