Long known as the Steel City, Pittsburgh has transformed itself into a modern, bustling metropolis where arts and culture thrive, historic buildings have been reimagined into trendsetting restaurants, breweries, and distilleries, and the city’s iconic three scenic rivers form the backdrop for a Great American Getaway. Just a two-hour drive from Cleveland and three-hour drive from Columbus, OH, we have put together a 48-hour getaway guide that maps out some of our favorite and top picks to see, do, and devour to help you pack the most into your trip to Pennsylvania’s second largest city.
Please note, this itinerary is meant to serve as a general guide. Before you depart on The Great American Getaway to Pittsburgh, we highly recommend you check our suggested places to visit for any seasonal hours of operation and available offerings.
Day One
Afternoon — Arrive in Pittsburgh and check into your choice of accommodations (keep scrolling for our picks at the bottom of this page).
Once you’ve settled in—or if you have some time for a pit-stop before check-in—enjoy lunch at one of Eat’n Park’s many locations. Well known for their Smiley Cookies and freshly baked pies, this casual family-owned restaurant chain was founded in Pittsburgh in 1949. Their endless Soup, Salad & Fruit Bar features fresh fruits and vegetables sourced locally through their FarmSource program. Hand-breaded fish, homemade chicken noodle soup, and their classic Superburger are just a few of their fan favorites.
Next, embrace your artistic side with a visit to the Andy Warhol Museum. Housing the largest collection of Warhol art, films, and archives in the world, including his iconic “Campbell’s Soup Cans,” the museum’s seven floors are filled with interactive experiences and displays. You can purchase your tickets online or at the door. Check out their public programs and performances webpage and events calendar for the latest news on all the exciting things happening at this one-of-a-kind art museum.
More eclectic art experiences are just around the corner. Take a scenic 20 minute stroll through the North Side and stumble upon Randyland, an outdoor artistic wonderland. You won't miss the vibrant colors and creativity that went into creating this iconic Pittsburgh stop that's become "one of the most photographed locations on Instagram."
Evening — Before dinner, take a trip up the Duquesne Incline to watch a stunning sunset over the city. One of the most iconic attractions in the city, this historic incline car takes you up to the observation deck to view what USA Today Weekend Magazine calls one of the "10 most beautiful views in America." Be sure to stop in the museum at the incline’s top station to learn about this iconic mode of transportation. You can even see the original machinery with its wooden gear teeth and today’s machinery that propels the cable car along nearly 800 feet of rail line.
Feeling hungry? The Original Oyster House, the city’s oldest bar and restaurant at 153 years young, is located in the heart of downtown Market Square. A designated historic landmark by the Pittsburgh History and Landmarks Foundations, the unique tavern’s menu is filled with delicious seafood options, from their jumbo fish sandwich to award-winning crab cakes to their “Cod Father” platter. The Original Oyster House will satisfy any seafood craving!
Not a seafood lover? No problem! We got you. Located just steps away from the incline’s terminal atop Mount Washington, elevate your dinner experience at Altius. With spectacular views of the Pittsburgh skyline, upscale, contemporary American cuisine, and elevated cocktails, this AAA four-diamond-rated restaurant is a popular dining spot especially for special occasions so reservations and business casual attire are required.
End the night with a delightful cocktail and the sounds of smooth jazz at Con Alma, a jazz bar named “One of the 27 Best Bars in America” by Esquire Magazine.
Day Two
Morning — Fuel up for your first full day in the Steel City with a caffeine kick and a bite from Redhawk Coffee Roasters at their Oakland location. This small Pittsburgh-based roastery sources and roasts the sweetest, most vibrant coffees it can find from around the world.
Spend your morning at the Phipps Conservatory and Botanical Gardens. This must-see for flower and plant enthusiasts, families seeking things to do in Pittsburgh, and friends looking for Instagram-worthy photo-ops offers a learning landscape from start to finish. Take a self-guided tour and explore their extensive collections of flora and artwork on your own or embark on a one-hour professionally guided tour to learn the fascinating history behind their astounding plant collections. This option is perfect for exploring the gardens with a small group. You'll want to buy your tickets online to secure your preferred date and time to explore this amazing destination.
Afternoon — For lunch, walk on over to the Union Grill, which boasts 30 years of serving big portions of home-cooked, “simple and good” food and strong drinks at a value price. Their claim to fame is the Turkey Devonshire served in a crockery skillet and featured in numerous publications and most recently on The Travel Channel’s “Delicious Destinations” with Andrew Zimmern.”
Right across the street you’ll find the Carnegie Museum of Natural History, a Pittsburgh destination you won't want to miss. With fascinating galleries and exhibits featuring tens of millions of objects and specimens from throughout the world and down through the ages, nature’s finest is on full display and sure to delight all ages and interests. With so much to see and experience, be sure to purchase your timed ticket(s) to guarantee entrance for your preferred date and time.
Evening — Make your way to your evening adventures along Three Rivers Heritage Trail. Designated as a National Recreation trail system in the region, this 33-mile trail stretches throughout the city with segments along all three rivers and a variety of access points throughout the city. Be sure to end up in the historic Strip District where shopping and savory scents of iconic Pittsburgh eats await.
No trip to Pittsburgh would be complete without a pilgrimage to Primanti Bros.’ original Strip District location. Named one of “America’s Classic Restaurants” by none other than James Beard, this classic has been serving up its Pitts-burger® sandwich since 1933. Be sure to arrive hungry because this massive sandwich starts off with two thick slices of Italian bread piled high with your choice of grilled meat, a big slice of melted Provolone, a mound of hand cut french fries, sweet yet tangy cole slaw, and topped with two slices of fresh tomato. It’s a true Pittsburgh experience all its own!
If you’re not too full and up for more fun, hop over the river to Penn Brewery, the city’s oldest, for a nightcap. They began by brewing up classic lagers and German beer styles, adhering to the strict quality standards of the 16th-century Bavarian Reinheitsgebot purity laws, but have since expanded their lineup to include IPAs and other contemporary styles such as chocolate and pumpkin beers. However, they’ve always stayed true to their quality craftsmanship, brewing all beers by hand with top-tier barley and hops, helping them to win 20 Great American Beer Festival® and World Beer Cup® medals.
Day Three
Morning — Begin your final day at Lawrenceville’s Espresso A Mano, one of Food & Wine’s “Best Coffee Shops in America” list in 2019, which was two years before they started roasting their own coffee and gotten even better.
Then, spend the rest of the morning and early afternoon strolling through Lawrenceville, a large, historic neighborhood in Pittsburgh that's often called one of the city's hippest areas. Home to many artists and designers, this trendy neighborhood hosts some of the city's biggest arts events, has one-of-a-kind shops, and an awesome dining scene.
Afternoon — Before packing up and concluding your getaway, grab lunch at Smoke, a premium taqueria in Lawrenceville serving scratch-made barbecue-forward tacos amongst other delicious fusion favorites.
Add A Day
Not ready for your Great American Getaway to Pittsburgh to end? Extend your stay to explore even more of southwestern PA. The small town of Bedford is a two-hour drive east and known to be a Hallmark-movie-like town. Charming and historic all year round, it especially comes to life during the holidays. Here you can spend a leisurely day strolling the many small businesses downtown. If you want to stretch your legs and are up for even more of an adventure before hitting the road home, Bedford is a short drive from Shawnee State Park, which is one of PA’s 124 state parks and is made up of 3,983 acres of the state’s scenic Ridge and Valley Province. The park is open every day of the year, sunrise to sunset, and admission is free.
Places to Stay
Hampton Inn & Suites Pittsburgh-Downtown — With warm hospitality and a prime location, the Hampton Inn & Suites Pittsburgh-Downtown offers a delightful blend of comfort and convenience, all at an affordable price. Nestled in the heart of Pittsburgh's vibrant downtown, the hotel provides easy access to the city's top attractions, including the bustling Market Square and the cultural richness of the Strip District. The hotel features modern and spacious rooms with plush bedding and a complimentary hot breakfast each morning, a fitness center so you won’t have to forego your daily workout, and an indoor pool.
The Priory Hotel Pittsburgh — Featuring a captivating combination of historic charm and modern amenities, The Priory Hotel provides a unique home base for your Pittsburgh getaway. Located in the historic Deutschtown neighborhood, this former Benedictine monastery now boutique hotel offers a range of accommodations, from cozy rooms to luxurious suites. After a full day of exploring the Steel City, indulge in delectable cuisine at the on-site Monks' Bar, which serves up an array of locally sourced dishes and craft cocktails in a relaxed atmosphere.
Kimpton Hotel Monaco Pittsburgh — The Kimpton Hotel Monaco Pittsburgh offers a luxurious retreat in the heart of downtown Pittsburgh. From the moment you step into the lobby, you’ll be greeted by an atmosphere that seamlessly marries sophistication with whimsy. The hotel offers a range of amenities including elegantly appointed rooms and suites featuring unique decor and plush bedding for a restful night's sleep. Culinary delights await at The Commoner, the hotel's acclaimed restaurant, serving up innovative American cuisine crafted from locally sourced ingredients. After a full day of exploring Pittsburgh’s wonders, unwind and relax at the rooftop Biergarten with its stunning views of the city skyline and handcrafted cocktails. For those looking to rejuvenate, the hotel provides a fitness center equipped with state-of-the-art equipment.
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