Best Driving Vacations: Adventures in Pittsburgh

Jillian Span Hofbauer

Once known primarily for producing steel and coal mining, Pittsburgh has enjoyed the highs and endured the lows of its strong industrial heritage. What remains constant about the steel town—affectionately dubbed the “City of Bridges”—is that its colorful blue-collar history combines with the locals’ deep sense of pride to exude a down-to-earth spirit that’s apparent in every corner.

In recent years, Pittsburgh has also reinvented itself as a vibrant and eco-friendly city immersed in recreational activities and natural beauty. Surrounded by rolling topography, wilderness and navigable waterways at the confluence of the Allegheny, Monongahela and Ohio rivers, its unique geographical location has made it an outdoor haven filled with parks, revitalized waterfronts and scenic urban views. Whether you explore by foot, bike, riverboat or incline cable car, there are many reasons to enjoy the outdoors and all of the diverse settings the city has to offer.

Sightseeing and Tours

Pittsburgh’s past as an American industrial center dates back to the French and Indian War in the mid-1700s. With a wealth of natural resources such as iron, coal, timber and natural gas, along with its position along key waterways, it became an ideal place for settlement and development.

As the city’s population increased, so did the need for innovative solutions to the region’s fragmented infrastructure. Bridge construction helped alleviate some of those navigational challenges—there are now 446 scattered throughout the city—but the area’s steep terrain presented problems for hilltop residents, who sought an easier way to commute and transport cargo to and from downtown.

Inspired by European engineering in the 1870s, a number of funicular railways, or cable cars, were built to scale the surrounding hillsides. Today, two of these historical methods of transit, the Monongahela (Mon) and Duquesne inclines, continue to operate along what is now known as Mount Washington, offering visitors as well as natives a nostalgic route to explore some of the most vibrant areas for nightlife and culture.

If you’re at the top of Mount Washington, take a ride down the Mon into the South Shore neighborhood to explore Station Square, a 52-acre riverfront shopping, entertainment and restaurant hub built on the former Pittsburgh and Lake Erie Railroad site. When visiting between April and early November, be sure to catch one of the choreographed water and light shows at Station Square’s Fountain at Bessemer Court before your return trip, heading up the rail to Mount Washington, the lively hilltop neighborhood that features businesses, parks and restaurants with dramatic views. Traveling up and down the Duquesne Incline, which isn’t far away, offers unmatched vistas of the city’s skyline, rivers and famed sports stadiums. Peruse its on-site exhibit for a brief history lesson, and stop by the gift shop for a souvenir on your way out.

Though it’s hard to beat the panoramic scenes available from those iconic lookout points, there are plenty of ways to explore Pittsburgh up close and personal. Book a seat aboard the Gateway Clipper Fleet’s Three Rivers Sightseeing Cruise for a one-hour expedition featuring landmarks, bridges and architectural places of interest, or reserve a spot on one of Just Ducky Tours’ amphibious vehicles for an excursion that mixes the best of land and water. To take part in some game-day camaraderie, sail along with Steelers or Pitt Panthers fans to Heinz Field on one of Pittsburgh Water Limo’s “sailgate” parties or shuttle services.

Plenty of other sightseeing opportunities exist back on land. The Pittsburgh Party Pedaler, an all-pedal-powered vehicle, is a fun way to jaunt around the city when traveling with a group of eight to 16. Pedal your way through popular spots such as the Strip District, known for its vendors, produce stands, ethnic grocers and fish markets, or North Shore, home of the city’s sports venues and some of its greenest buildings, including the Children’s Museum of Pittsburgh, which offers an outdoor classroom for kids to explore the natural world.

If using good old-fashioned leg power to move around the city is right up your alley, then consider the many biking options available for both guided tours and creating your own journey. Bike the Burgh’s “Beauty of the Burgh” tour provides a well-rounded look at points of interest, but other options feature food and drink, neighborhoods and more. For a longer cycling trip, the city is the perfect access point to the Great Allegheny Passage, which begins at Point State Park and winds all the way to Cumberland, Maryland. Noble Invention Bike Touring makes planning the experience a breeze, with guided trips that include scenic views, overnight accommodations and small-town stops along the way.

Adventurous Activities

Want to satisfy your inner explorer? You’re in luck. Pittsburgh’s landscape beckons everyone from nature enthusiasts to weekend warriors with seasonal and year-round offerings. Start by heading to the waterways, where decades of cleanup and restoration have produced a thriving recreational scene.

Paddle along the buzzing riverfronts at your own pace in a solo or tandem kayak available for hourly rental through Kayak Pittsburgh. The season runs from May through October and prior experience isn’t necessary, making it an ideal activity for the whole family. A stand-up paddleboard excursion with SurfSUP Adventure is another way to get on the water, and it’s suitable for a variety of skill levels. But if you’re looking for a bolder challenge, try wake-surfing with Surf Pittsburgh. While most people book lessons during the warmer seasons, wet and dry suits are available for those interested in braving inclement conditions.

Cleaner waterways have also led to healthier ecosystems and better fishing opportunities, whether you prefer to cast from a tranquil creek off the beaten path or a more urban setting. To try a new take on the sport, Nocturnal Addiction Bowfishing offers a five-hour guided nighttime expedition that embarks from several locations.

Of course, enjoying Pittsburgh’s lush wilderness and many green-spaces can be an invigorating way to get back to nature any time of year. For a unique, hands-on experience, try the Go Ape North Park course, a treetop experience that includes zip lining, suspended obstacles and swings. With many parks around the area, there are also countless hiking and bike trails that vary in difficulty and length.

Frick Park is the largest regional park, encompassing 644 acres of land, and it’s known for extensive hiking trails and rugged terrain. It is also the site of some of the city’s restorative ecological efforts, including a costly initiative at Nine Mile Run, a beautifully revived waterway once damaged by sewage and steel mill waste. But hiking doesn’t have to be reserved only for secluded hills and forests; check out urban hiking with Venture Outdoors, which enables visitors to wind through neighborhoods, climb staircases and cross bridges all around the city.

Jillian Span Hofbauer is a Columbus-based writer who enjoys covering travel and is looking forward to her next trip to Pittsburgh.

If you are in the mood for a quick side trip, Pittsburgh is a 40-mile drive from the hometown and official archive of everyone’s favorite neighbor. The Fred Rogers Center, located on the St. Vincent College campus in Latrobe, Pennsylvania, is a public exhibit celebrating the life and legacy of its namesake television personality and champion of early childhood learning. Housing more than 18,000 items related to Rogers’ life and career, the free display features narratives, photos, videos, interactive components and many of the most iconic Mister Rogers’ Neighborhood pieces—his sweaters and shoes, Daniel Tiger’s clock, the puppets and, of course, the neighborhood trolley.

Far beyond just a place of tribute, the center actively works to continue promoting Rogers’ nurturing approach and message among new generations, says Karen Struble Myers, director of development and communications. Launched in 2003 under Rogers’ guidance—it opened after his death later that year—the center was created with a mission to help children become confident, competent, caring humans.

“Fred never wanted something that would be a museum to his legacy. It was his vision to have continuing work that supported children, educators and parents,” Struble Myers says. Along with community initiatives related to the social and emotional development of children, the center also focuses on the importance of educational technology and digital media use.

For an intimate look at Rogers’ life, check out the 2018 documentary “Won’t You Be My Neighbor?”—a project made in close collaboration with the Fred Rogers Center.

Mister Rogers' Neighborhood