Even if you’ve lived in Pittsburgh your entire life, there’s always something new to be learned. With these city tours, plunge into local history when out-of-towners come to visit or if you’re looking to expand your knowledge of the City of Bridges. 

‘Burgh Bits and Bites Food Tours

Multiple Locations
Food-tasting tours of Pittsburgh’s historic neighborhoods, including an international food tour in the Strip District, an all-ages tour through Brookline, and more. 

Carrie Blast Furnace Heritage Tours

801 Carrie Furnace Boulevard, Rankin-Swissvale
Dive into Pittsburgh’s steel-industrial past with nonprofit heritage organization Rivers of Steel’s guided tour of the Carrie Blast Furnaces National Historic Landmark. Love art? Opt instead for the Arts & Grounds Tour, which includes a stop at the famous Carrie Deer, a massive sculpture made of tubing and metal. 

City Steps Walking Tour

Multiple Locations
Pittsburgh is famously known for its 700-plus sets of city-owned steps, the most public staircases in any US city. Join Laura Zurowski, aka Mis.Steps, and North Side-based cidery and bottle shop Threadbare Cider & Mead on this historical two-hour walking tour through city steps in two North Side neighborhoods. Bonus: each tour ends with a glass of cider! 

Pittsburgh History & Landmarks Foundation Tour

100 West Station Square Drive
This nonprofit historic preservation organization offers a variety of informative tours, including both self-guided and customized tours. Want to set out on your own? We recommend downloading the self-guided Bridges & River Shores Walking Tour available as a free PDF via their website. Interested in a more guided experience? Register for a Specialized Architectural Tour. 

Pittsburgh Cemetery Tours

Pittsburgh is home to multiple park-like cemeteries, which encourage residents to enjoy the grounds while paying respect to those who have made it their final resting place. We recommend taking a self-guided tour, with the help of a guided map available online, through the historic Allegheny Cemetery, featuring an array of tree-lined paths and wooded hillsides. Also worth a visit is the Homewood Cemetery, which offers seasonal guided tours led by historian Jennie Benford. 

Molly’s Trolleys 

2524 Penn Avenue
Hop on an iconic bright red vintage-style trolley for a public sightseeing tour through some of Pittsburgh’s most popular neighborhoods. Two 90-minute tours depart daily from the Strip District and include a ride on the Duquesne Incline. 

Doors Open

Multiple Locations
Since its launch in 2016, this nonprofit boasts an impressive 22,000+ visitors on its tours of local landmarks, historic buildings, and interesting spaces. Join Doors Open for tours of the Poale Zedeck Synagogue in Squirrel Hill, the historic Pittsburgh Stained Glass Studio in the West End, Millionaire’s Row in Shadyside, and more. 

Explorer Riverboat Tour

Rivers of Steel Dock
The Uniquely Pittsburgh Sightseeing Tour is another offering from nonprofit heritage organization Rivers of Steel. This 90-minute seasonal tour takes guests on board the Explorer riverboat, combining beautiful views of the Downtown skyline with unique stories of the region’s history. 

Story by Lisa Cunningham

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Kids aren’t the only ones that get to have fun. Tap into your inner child with these adult-friendly venues where you can feel like a kid.

Pins Mechanical Co.

407 Cinema Drive
Two words: adult slide. Yes, you read that right. In addition to two floors of foosball, pinball, duckpin bowling, ping pong, and bocce, Pins is home to two giant silver slides that will glide you right into nostalgia. 

Coop De Ville

2305 Smallman Street
Delectable fried-chicken dishes and Southern eats paired with entertaining activities, including duckpin bowling, arcade games, pinball, and more, make for a memorable night, regardless of age. But for those over 21, two different bar menus elevate an already amusing experience. 

Shorty’s Pins x Pints

The Waterfront and North Shore
Bocce courts, vintage arcade games, duckpin lanes, pinball machines, foosball tables, and shuffleboard tables: old-school recreation is the heart of Shorty’s Pins x Pints, promoting friendship and community among all who enter. 

Barcadia

25 Market Square
Above The Market Exchange lives this festive bar offering a mix of traditional arcade games and pinball. Sip on Barcadia’s handcrafted cocktails while chowing down on bites available from Slider Vibes. Oh, and there’s a speakeasy located in the back, but maybe that was meant to be kept a secret …. 

Arsenal Bowl

212 44th Street
Dubbed “Where old-school-bowling vibe meets nightclub atmosphere” by the New York Times, for those who would rather skip the duckpin bowling fad, Lawrenceville’s Arsenal Bowl is the perfect spot to indulge in the timeless activity. For an even louder blast from the past, check their Wednesday Rock N’ Bowl or Thursday’s ’80s/’90s night. 

Story by Jordan Snowden

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Janera Solomon, creative writer, cultural strategist, and former executive director of the Kelly Strayhorn Theater, suggests a selection of innovative Pittsburgh theater companies. 

City Theatre

One of the city’s smartest contemporary theater companies, City Theatre constantly surprises with engaging and diverse performances. Expect a season full of relevant plays focused on current issues, all performed in the theater’s beautiful South Side venue. 

Pittsburgh Playwrights

Led by founder Marc Clayton Southers, Pittsburgh Playwrights prides itself on its African American roots with a mission to produce Pittsburgh-themed plays and works by local racially- and culturally-diverse playwrights. This year, the company is celebrating its 20th anniversary, with a lineup including August Wilson’s Tony-nominated drama Joe Turner’s Come and Gone, which will be performed outdoors at the August Wilson House in the Hill District. 

Quantum Theatre

This progressive company, founded by Karla Boos in 1990, produces intimate and trailblazing theatrical performances in unexpected places. Recent offerings included an immersive theatrical experience in a Downtown church, an edgy contemporary take on Faust in Frick Building’s Tenant Innovation Center, and a Shakespearean tragedy on the site of Carrie Blast Furnaces National Historic Landmark. 

Story by Janera Solomon

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Pittsburgh is surrounded and intersected by bodies of water. It’s why we’re called the City of Bridges: so that we can get from point A to B without getting wet! Test the waters with recommendations from Riverlife president and CEO, Matthew Galluzzo that get you on or close to Pittsburgh rivers.

ArtWalk on the Allegheny

ArtWalk on the Allegheny, a project of Riverlife, the Pittsburgh Cultural Trust, and the Allegheny Regional Asset District, brings immersive artwork and engaging programming along two miles of riverfront trail on the Allegheny between Point State Park and the Strip District. Commissioned public artwork like Invisible Ecologies, an installation of industrial birdhouses by Future Green Studios, and Black Flowers, a mural by artist Camerin “Camo” Nesbit, are some of the pieces you’ll find along the way. 

Allegheny Landing Park & Public Dock

12 Federal Street
Riverlife led and recently completed construction of the public boat dock at Allegheny Landing. With its colorful public art and gorgeous skyline, it is the perfect location for photographers, picnickers, and boaters alike. Join the Tri-Anglers on Wednesdays for Venture Outdoors’ free lunchtime fishing program, where everything is provided for you to get some fresh air and catch bass, catfish, carp, and more. 

Gateway Clipper Fleet

350 W. Station Square Drive
Climb aboard the Good Ship Lollipop. There’s no better place to experience the city from the water than aboard one of the famous vessels of Pittsburgh’s Gateway Clipper Fleet. Tour guides are full of fun facts and information about Pittsburgh from the ground — or, rivers — up. 

Complete the Loop

West End Bridge to 31st Street Bridge
Ride, walk, or jog the Loop. As Riverlife continues to move forward with the Complete the Loop vision, there are a number of signature moments along the 15-mile, 1,055-acre network of riverfront trails, open spaces, and parks between the West End Bridge, the Hot Metal Bridge, and the 31st Street Bridge. Make sure to check out our riverfront gems: the Water Steps on the North Shore, the majestic fountain at Point State Park, and the South Shore Riverfront Park. 

Story by Matthew Galluzzo

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The bookstore experience is made even better with live performances. Stephanie Flom, executive director at Pittsburgh Arts & Lectures, and Heather McAdams Caldwell, content strategist at Littsburgh and publisher at Bridge & Tunnel Books, share three local bookstores to catch a show.

White Whale Bookstore

4754 Liberty Ave
Locally owned, neighborhood bookstore. Great selection of literary and local titles. Beautiful renovation/expansion provides quiet, professional space for readings, plus cappuccinos and Millie’s ice cream! 

City of Asylum

40 W. North Avenue
Knowledgeable staff, great selection of books, especially translations and children’s collections. It’s wonderful to support the important work of City of Asylum and the exiled writers they house in their residency program. Great performance space to hear from writers and listen to music. 

Penguin Bookshop 

417 Beaver Street, Sewickley
Penguin Bookshop hosts a can’t-miss writers’ series about twice a month with award-winning writers. The conversations are always fun and engaging. 

Story by Stephanie Flom and Heather McAdams Caldwell

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Photographer Matt Dayak found it a challenge to narrow his favorite hikes down to a list of six. After reminding us that Frick and Schenley Parks are great options right in our backyards, he chose some destinations to consider next time you are looking to get outside. 

Bruceton Mills

WV, 80 minutes
Coopers Rock in West Virginia is more than just a spectacular scenic overlook with views of the Cheat River and Appalachian Mountains in every direction. With around 50 miles of trails there is plenty to explore. A good trail to start with would be Raven Rock trail. If you are into history, check out the Clay Furnace Trail to visit the Henry Clay Furnace built in 1834. 

McConnells Mill State Park

Portersville, 40 minutes
Flowing water always makes for better hiking in my opinion and McConnells Mill has a great deal of it. Probably my favorite route here, hiking along the Slippery Rock Creek Gorge, created by the draining of glacial lakes thousands of years ago, is absolutely enchanting on a beautiful day. It gets busy on the weekend here so go early. 

Forbes State Forest

Laurel Highlands, 75 minutes
There are so many options for hiking and things to see in Forbes State Forest. One of the coolest things there is Mt. Davis, the highest point in Pennsylvania at 3,213 feet. Be sure to climb the observation tower for the best views. The Laurel Highlands Trail runs right through Forbes, too, and with over 70 miles total you can make your own out and back with as much distance as you like. 

Monongahela National Forest 

Huttonsville, WV, 2 hours
This one takes a little bit of road trip but it is totally worth it because this forest makes up one of the most ecologically diverse areas in the United States. One hike can feel like three different areas of the country. If you like hiking with some elevation gain you will find it here, ranging from around 1,000 feet to almost 5,000 feet. With nearly one million acres of breathtaking scenery, you will not run out of new adventures in this vast forest. 

Wingfield Pines Conservation and Nature Preserve

Upper St. Clair, 25 minutes
This is a small 87-acre conservation area in the Pittsburgh suburbs. The best thing about Winfield Pines is the environmental work Allegheny Land Trust is doing to mitigate the damage done from mining the area. It has a cool wetland boardwalk that is great for bird watching and you might even spot a beaver or two. 

Cuyahoga Valley National Park

Ohio, 1 hour, 45 minutes
A lot of people don’t realize there is a national park less than two hours from Pittsburgh, and with nearly 100 waterfalls, it is a great spot for hiking. There are easy hikes that are very accessible for anyone not looking for anything too serious. A great place to start there would be The Ledges Trail as it weaves through massive moss-covered rock walls formed over 300 million years ago. 

Story and Photography by Matt Dayak

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I’ve been all over the world, but some western Pennsylvania attractions rival what I’ve seen in foreign countries. When I first visited Pittsburgh, I had no clue that I’d become a travel writer. I was there for a pre-college academic program at Carnegie Mellon—nerd camp, as we called it—in architecture. But a few college-major changes and lucky career breaks later, I’ve spent decades traveling the world and writing about it for the likes of Forbes and Condé Nast Traveler. 

I’ve seen a lot, but I still think fondly of that summer in Pittsburgh. It was my first time outside the 20th-century cities of the West. Pittsburgh is a place with a history almost as long as that of the United States. It has solid foundations in culture and architecture, and a classic melting-pot heritage. And some of Western Pennsylvania’s best attractions stand up to the ones that I’ve traveled much farther to see. 

Western Pennsylvania’s Best Attractions

Fallingwater

1491 Mill Run Road, Laurel Highlands

Fallingwater is the most famous work by America’s most famous architect. Frank Lloyd Wright’s signature project was designed in 1935 for the Kaufmann family. It’s located in Pennsylvania’s Laurel Highlands, 70 miles from Pittsburgh. It’s hailed as an excellent example of organic architecture, a style meant to symbolize the harmony between people and nature—the boundary between indoors and out is a blurry one. Since it opened to the public in 1964, it has welcomed more than six million visitors, and in 2019 it was designated a UNESCO World Heritage List. 

Allegheny County Courthouse and Jail

436 Grant Street

Henry Hobson Richardson’s Allegheny County Courthouse and Jail has been called the best building of the 19th century. Richardson, who designed the building in 1883 but didn’t live to see its completion in 1888, is one of the greatest American architects in history. His final work is his masterpiece. Along with its impressive Renaissance and Romanesque architecture, the building is distinguished by its 229-foot-high tower, soaring arches and dignified columns, and picturesque, turreted rooflines. 

The Andy Warhol Museum

117 Sandusky Street

Spanning seven floors (plus an underground level), The Andy Warhol Museum showcases the Pittsburgh-born artist’s life story and explores his legacy through the largest collection of his work and archives in the world. Along with the permanent collection and rotating exhibitions, the museum has a robust events calendar. The museum hosts talks children’s workshops, music performances, and LGBTQ+ programming. Its latest project is the Pop District, a youth-led transformation of the city’s eastern North Shore through arts, creativity, and economic development. 

Phipps Conservatory and Botanical Gardens

1 Schenley Drive

Phipps Conservatory has been delighting visitors for more than a century with its 14-room glasshouse and 15 acres of gardens. Even before sustainability became a buzzword, the conservatory has lived up to its name, promoting practices that tread lightly on the environment. The Welcome Center is LEED-certified, and the Center for Sustainable Landscapes is considered one of the greenest buildings on Earth. It’s refreshing to visit a botanical garden that isn’t just a Victorian throwback but shows a way to a better future. 

Laurel Caverns

1065 Skyline Drive, Farmington

It’s not only the American West that has stunning caves and rock formations. Laurel Caverns in Farmington is Pennsylvania’s largest cave, with more than four miles of passages to explore. The limestone caves were likely formed before the building of the Pyramids, and arrowheads found near the entrance reveal that Native Americans used them. Spelunkers can sign up for caving excursions on weekends. 

Flight 93 National Memorial

6424 Lincoln Highway, Stoystown
While it’s not a fun attraction, the monument bears witness to a day that changed history forever and pays tribute to the 40 heroic passengers and crew who prevented an attack on the US Capitol. 

Story by Ann Abel

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Ready for a bit of exercise? Eric Boerer, Bike PGH’s advocacy director, suggests we explore the North Side and Mon Valley on two wheels with the Pittsburgh bike trails. 

North Side Tour 

One of my favorite bike rides, which can be done any time of day, is a sub-20-mile loop of the North Side that incorporates river trails, bike lanes, and park roads. It’s easily accessible from Downtown Pittsburgh, too. Cross the Sixth Street Bridge, head to the bike lanes around Allegheny Circle, then make your way to the East Street bike lanes, where the climb takes you close to Riverview Park. Once in the park, there’s a great road loop (with very few vehicles) around Riverview Park where I often take a few laps, being sure to check out the view from the Allegheny Observatory at some point. Once done, drop down to Woods Run and catch the Chateau Trail along the north bank of the Ohio River straight back to the Point. Not only is it a great, low-traffic bike ride, but it’s a stellar tour of Pittsburgh’s North Side neighborhoods. 

Mon Valley Tour

One of my favorite river trail rides involves exploring both banks of the Monongahela River, especially when I want to zone out, pedal for as long or short as I want, and not worry about cars. You can ride the Eliza Furnace Trail from Downtown to the Hot Metal Bridge. At the Hot Metal Bridge, on top of seeing one of the best views of Downtown, you can decide to ride into Hazelwood or cross the river to the South Side and connect to the Great Allegheny Passage, also known as the GAP Trail. While the GAP trail heads all the way to Cumberland, MD (and onward to DC via the C&O Canal Trail), you don’t need to ride that far to explore the historic business districts of the South Side and Homestead. It’s an easy ride back along the Mon through the South Side. The Smithfield Street Bridge will take you back to Downtown, where you can connect along a series of streets with bike lanes to relax next to the fountain at Point State Park. 

Story by Eric Boerer

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Are you ready to laugh? We sure are, thanks to these comedic Pittsburgh locations.

Arcade Theater 

943 Liberty Avenue
For the past 10 years, Arcade has been a learning center and hub for Pittsburgh comedy, bringing together improv, standup, sketch, music, and more. It’s a comedy staple in the city of Pittsburgh. 

Kingfly Spirits

2613 Smallman Street
Not a traditional comedy theater, Kingfly offers its venue to a multitude of different local comedy producers helping to expose the local comedy scene to a whole new audience. Plus, they consistently bring in national headliner, Nick Colletti. 

brillobox 

4104 Penn Avenue
I’m completely biased on this pick because I curate the comedy night at brillobox. It’s my guarantee of seeing my favorite local and out-of-town comedians. This year, all shows are free but we are partnering with local nonprofits to collect much-needed items. Join us every second Tuesday of the month for a comedy show for a different cause! 

Story by Gab Bonesso, award-winning standup comedian and mental health public speaker.

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