Venture Down to Dead Man’s Hollow

Nestled in Pittsburgh’s Laurel Highlands neighborhood, Dead Man’s Hollow is one of Pittsburgh’s spookier natural attractions. This eerie ravine earned its name from the legends of bodies being dumped in the gorge during the Whiskey Rebellion. Visitors to the Hollow today can explore the gorge’s ghostly folklore and striking rock formations on an easy 1-mile loop trail. The haunting beauty of the gorge is most prevalent in the fall when the autumn foliage paints the ravine in brilliant shades of red and orange. Your group can also spy rare plant species, traverse rock ledges, and explore small caves throughout the hike. After your adventure, hop back on your Party Buses Pittsburgh charter bus and get ready for your next hidden gem!

Address: 327 Curtis Ave, Pittsburgh, PA 15237

Tour the Underground Railroad Museum

Located in Allegheny West, the Underground Railroad Museum provides an immersive look at the network that helped enslaved people find freedom in the North. Your group can walk through the museum’s recreated Underground Railroad sites, including hideouts, tunnels, and stations. Exhibits also showcase the stories of brave abolitionists who put their lives on the line to fight injustice. This eye-opening museum brings an important part of Pittsburgh’s role in the anti-slavery movement to light. Groups of all ages will find the museum incredibly impactful. A trip to the Underground Railroad Museum will inspire your crew and provide plenty of opportunities for meaningful discussion afterwards.

Address: 820 East Warrington Ave, Pittsburgh, PA 15210

Marvel at Goddard State Park’s Space Art

What may seem like an average state park transforms into a whimsical art display when the sun goes down. Goddard State Park is home to Cosmos Mystery Area, an art installation by famed artist Ton Yuen. By day, the concrete sculptures scattered throughout the woods look like abstract shapes, but once night falls and the art is illuminated, the sculptures reveal their true forms – depictions of space shuttles, planets, and more. Your group can wander through the park as day fades into night and watch this magical space-themed art display come to life. It’s an experience unlike anywhere else in Pittsburgh! Don’t forget to look up at the sky for some real-life space objects like constellations while you explore Ton Yuen’s cosmic sculptures.

Address: 119 Goddard Park Rd, Sandy Lake, PA 16145

Get Lost in Trundle Manor

Trundle Manor is certainly one of the quirkiest attractions your group will visit in Pittsburgh. This whimsical house museum is home to eccentric creations crafted by artists Leslie and Velda. Wander through rooms filled with strange taxidermic creatures and macabre curiosities for a peculiar and unforgettable experience. Although it may seem a bit bizarre at first glance, Trundle Manor is all in good fun. Your group will get a kick out of the darkly comedic exhibits and over-the-top Halloween-inspired decor. While it’s not for the faint of heart, Trundle Manor is a can’t-miss destination for adventurous groups looking to explore Pittsburgh’s weirder side.

Address: 730 Trundle St, Swissvale, PA 15218

Travel Back in Time at Meadowcroft Rockshelter

Meadowcroft Rockshelter offers a unique look into Native American history and life in ancient Appalachia. Archaeologists have uncovered evidence that 16,000 years of continuous human occupation took place at the site. When your group visits this fascinating National Historic Landmark, you’ll get to walk among the remains of ancient structures, tools, and artifacts. The museum also features exhibits detailing how early settlers in the region lived off the land and interacted with the natural resources around them. Meadowcroft Rockshelter provides amazing insight into what daily life was like for early inhabitants of the region over 16,000 years ago. It’s an incredible opportunity to experience ancient history up-close.

Address: 401 Meadowcroft Road, Avella, PA 15312

Play Vintage Arcade Games at Arcade Comedy Theater

For some nostalgic, retro fun, your group can spend an evening at Arcade Comedy Theater in Downtown Pittsburgh. True to its name, this intimate theater boasts a collection of 40+ vintage arcade and pinball machines that are free for anyone attending a show to play. Your group can challenge each other to games of Pac-Man or race classic arcade driving games before enjoying hilarious improv and sketch comedy shows. Arcade Comedy Theater’s affordable tickets and bring-your-own-beer policy make it a perfect night out for adult groups and anyone who feels nostalgic for old-school arcades. Relive the magic of yesteryear gaming and get some great laughs at this uniquely Pittsburgh theater.

Address: 859 Liberty Ave suite 201, Pittsburgh, PA 15222

Marvel at the Mind-Bending Art of the Mattress Factory

The Mattress Factory is Pittsburgh’s one-of-a-kind contemporary art museum. Unlike any traditional art museum, the Mattress Factory hosts “installation art” exhibits that completely transform rooms into immersive worlds. Your group can walk through mind-bending rooms with dizzying black and white lines, experience eerie pitched-black mazes, see furniture creepily sealed into walls, and so much more. From funhouse-esque rooms to conceptual minimalist exhibits, the rotating installations at the Mattress Factory range from playful to thought-provoking. It’s a fantastic destination for teen groups and art lovers to spark conversations and challenge perceptions through art.

Address: 500 Sampsonia Way, Pittsburgh, PA 15212

Tour Pittsburgh’s Historic City Steps

Strewn across Pittsburgh’s hillsides are hundreds of staircases, or “city steps” as the locals call them. These impressive, mural-adorned steps aren’t just transportation infrastructure – they’re historic landmarks steeped in community heritage. Your group can spend an active day touring some of the most fascinating steps around Pittsburgh. Must-see city steps include the steep Canton Avenue Steps in Beechview and the blooming spring garden steps in South Side Slopes. Or check out the educational Steps of Pittsburgh guided tour to learn about everything from engineering feats to immigrant history behind the steps. Exploring Pittsburgh’s iconic steps gets your group moving while discovering the city’s hidden stories.

Plan Your Trip with Party Buses Pittsburgh

Don’t miss out on anything during your hidden gems tour of Pittsburgh! Party Buses Pittsburgh offers transportation services for groups of all sizes so you can keep your trip flexible and focus on creating unforgettable memories. Our team handles the driving so you can fully experience Pittsburgh’s secret wonders. Reach out to us at 412-894-0966 to start planning your custom group adventure today!