Pittsburgh Road Trip: Massive Things To Do List (with Photos!)
Whether you’re looking for an epic Cleveland road trip destination, or visiting from further away, a Pittsburgh road trip is a great way to spend a long weekend. While we’ve been to the city many times in the past, our most recent trip made me love visiting Pittsburgh even more. Here’s everything we were able to do in a 3-day road trip weekend (plus a few bonus stops we’ve been to before that are worth mentioning that could easily be fit into the itinerary)
where to Stay in Pittsburgh
Stay in Style: Our Favorite Hotel
Hotel Monaco Pittsburgh 620 William Penn Pl, Pittsburgh, PA 15219
We are huge fans of the Kimpton line of hotels and try to stay at one any opportunity we get. We’ve stayed at a Hotel Monaco before in Chicago and other Kimpton locations and knew we were in for an eclectic treat! This stylish hotel is full of beautiful colors, patterns, art, and more. Our room was a delightful mix of pattern and color with an oh-so-comfy bed.
We definitely enjoyed the cocktail hour Kimpton is well known for each evening and their rooftop bar was a great way to end a long day of exploring while looking up at the stars. We didn’t get a chance to dine at their in-house restaurant but it looked lovely and delicious. (next time!)
The Neighborhood
Green Getaways with epic city views
Whenever we visit a big city we love to balance that with getting outdoors. On our Pittsburgh road trip, we stayed in the city and enjoyed several outdoor attractions.
Ride the Inclines
Duquesne: Visit | 1197 W. Carson St., Pittsburgh, PA 15219
Monongahela: Visit | 8 Grandview Ave., Pittsburgh, PA 15211
An affordable and fun way to experience Pittsburgh is to ride one of the two remaining inclines operating in the city, the Duquesne and the Monongahela Inclines. These rides go up the steep banks along the Monongahela River and are a great way to see an expansive view of the Pittsburgh Skyline, iconic bridges, and the 3 rivers that intersect in the heart of the city. On nice days you should expect a wait to ride so get there early. We didn’t ride this visit, but have in the past and feel this is a must-do when visiting Pittsburgh.
What’s the difference?
Duquesne Incline (pronounced “doo-kayn”) has red cars and you can see it from Point State Park
Monongahela Incline (pronounced “muh-naang-guh-hee-luh”, or commonly referred to as the “Mon Incline”) has yellow on their cars and is visible from the South Shore.
See The City from Above
Visit | Multiple locations along Grandview Avenue, Pittsburgh, PA
Nestled along the edge of the Mount Washington neighborhood between the two inclines are a series of viewpoints and a new-ish city park on the hillside called Emerald View Park that gives expansive views of the Pittsburgh skyline, rivers, and iconic bridges. We only had time to visit the viewpoints, but the park looked like a great way to take in nature in the city and is on our list for our next visit.
Stroll Along 3 Rivers at Point State Park
Visit | 601 Commonwealth Place, Pittsburgh, PA
This park is at the confluence of the Ohio, Monongahela, and Allegheny Rivers and is a lovely recreational space in the heart of Downtown, Pittsburgh. Our last visit was during August and we enjoyed a break from the heat at the Point State Fountain right at the corner where the rivers meet. This fountain shoots water 150 feet in the air and the mist from the breeze was delightful in the heat of summer. I also recently learned the city rejected a fountain design from Frank Lloyd Wright for the one it currently has.
Looking for another hardworking (former) steel town that has built itself back up? Check out nearby Cleveland, Ohio – only about 2-hours away from Pittsburgh. I have a whole guide dedicated to Cleveland here.
Art Everywhere: Pittsburgh’s vibrant arts scene awaits
No Pittsburgh road trip is complete without experiencing some of the incredible art museums and exhibits throughout town. Here are a few favorites.
Enjoy the Oddest Art Exhibit
Visit | 1501 Arch St, Pittsburgh, PA 15212
You won’t miss this popular North Side destination and how could you? It’s one of the most colorful places in all of Pittsburgh. Randyland is a free and unique, found-object art museum that is the perfect spot to add to any itinerary, especially if you’re visiting Pittsburgh for the arts as we were. So, set aside an hour or so to peruse the weird and wacky art that fills this uplifting and fun art museum and fill your day with fun.
Visit a Famous Local Artists Museum
Visit | 117 Sandusky Street Pittsburgh, PA 15212
One of the main reasons for our recent Pittsburgh road trip was to finally visit the Andy Warhol Museum. This trip coincided with my birthday, which I happen to share with this famous Pittsburg resident. The building was a well-laid-out multi-floor museum filled with the history of this odd artist whose iconic art helped shape the world of pop art and beyond. It’s a must-visit for any art lover, I learned so much!
Explore Art and History at the Carnegie
The Carnegie Museum of Art is attached to the Carnegie Museum of Natural History and both are so worth a visit. We saw so much incredible art, historic pieces, historic animals, and my absolute favorite area – the Hillman Hall of Minerals and Gems where I could have spent HOURS looking at their incredible gems and mineral collections. If you saw my camera roll, you would think I’ve never seen a pretty stone before haha.
When we arrived, we were greeted by a live group of musicians playing classic tunes on the horns while people enjoyed the day outside listening. We entered the museum, got our entry ticket tag, and then grabbed a quick bite at the museum restaurant The Cafe Carnegie. Then we walked through the art museum side before fitting in as much of the history side as we could. We did arrive kind of later in the day but were able to fit in a lot of great views.
Boutiques And Beyond: Exploring Pittsburgh’s Shopping Scene
Shop the Strip District
I love seeing former industrial places get a new life making community spaces to gather, shop, and explore. The Strip District is literally just that, a narrow half-mile long strip of land sandwiched between a huge hill and the Allegheny River. It’s a huge, gritty district full of former industrial buildings that are now filled with small and local businesses. There’s a lot to see and do, but here are a few places we really liked. Be sure to add this unique district to your Pittsburgh road trip.
Posman Books
Bright and cheerful bookstore with books arranged to stand out. Find a Millie’s Ice Cream stand inside this shop.
City Grows
Lots of awesome plants, planters, accessories and more.
Pennsylvania Macaroni Co.
Lots of pasta noodles, including some unique shapes, and everything you need to make delicious Italian food.
Grandpa Joe’s Candy Shop
A huge candy shop filled with just about any candy you can imagine, including an imported section.
Love, pITTSBURGH
Find all things Pittsburgh here from food items, decor, books, locally made goods and more.
Taste of Steel City
Indulge in Delicious Treats
Milkshake Factory
We’ve been visiting the Milkshake Factory since one of our first visits to Pittsburgh and it’s such a good, thick milkshake that it’s worth a stop.
Millie’s
Delicious homemade ice cream with lots of flavors.
Breakfast of Champions (be prepared to wait for these gems)
Kelly O’s Diner
According to the sign outside of their building this place is world-famous, the inside has local diner vibes. Be prepared to wait in line as there aren’t a ton of seats, but there is a lot of people wanting breakfast. We felt it was worth the wait.
Ritual House
This is a very Instagrammable restaurant with hanging flowers and extra decor all around. Breakfast was pretty good and we enjoyed our visit.
Great Spots for Lunch & Dinner
Bakersfield
This taco spot used to be in Cleveland and we miss it, so anytime we’re in a city that has one we have to visit. Delicious tacos and other Mexican dishes can be found here.
eMPORIO
Part of Sienna Mercato collection of restaurants (all conveniently in the same building) is Emporio, a meatball-focused restaurant. You choose a meatball style, sauce, toppings, and get a delicious bowl.
Pizzaiolo Primo
We were going to visit somewhere else for dinner but as we decided to get ice cream before dinner (because why not?) we saw someone with leftovers bag from this place and the branding looked nice so of course I looked into it and changed our reservations. Worth the wait. It was so good!
There you go! Plenty of ways to fill your itinerary for the perfect Pittsburgh road trip. Have fun!
Thank You For Reading!
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