Experience Pittsburgh’s Festive Spirit on the Jolly Trolley Holiday Sightseeing Tour
Difficulty
easy
Duration
1 hour
Fitness Level
Suitable for all ages and fitness levels; involves minimal walking
Overview
Hop aboard the Jolly Trolley for a one-hour vintage-style ride through Pittsburgh’s most festive holiday sights, featuring Santa, seasonal songs, and the city’s beloved landmarks.
Jolly Trolley Holiday Sightseeing Tour
All ages • 1 hour • Family-friendly • Saturdays + Sundays during the holidays
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About This Adventure
Experience Pittsburgh's enchanting holiday traditions aboard a vintage-style trolley! This one-hour tour, led by Santa, showcases festive sights like the iconic Mr. Rogers statue and the city's official Christmas tree. Enjoy singing holiday favorites, capturing memories, and even receiving a special gift, making it a delightful outing for all ages.
See Pittsburgh's holiday traditions come to life from the comfort of a vintage-style trolley!
Duration
1 hour
Tours run Saturdays and Sundays from November 23rd to December 21st, 2025.
About
The Jolly Trolley is a 1-hour long holiday sightseeing tour of Pittsburgh, perfect for all ages! Beginning in the North Shore, this tour takes you throughout the city to discover the wonder and magic of the holidays in a unique and festive way.
Learn interesting facts about Pittsburgh holiday displays and traditions from Santa himself! Take photos with our decked out trolley car, and sing along to holiday favorites! You won’t leave this trolley without becoming just a little bit more jolly. Special youth guests might even receive a small gift - sent all the way from the North Pole!
During your trip you will visit and see several holiday favorites of the city, including:
- The Mr. Rogers statue with a view of Point State Park
- Joseph Horne's 6-story tall historic tree
- PPG Plaza to view the ice skating rink
- The City of Pittsburgh's Official Tree outside of the City-County Building. You can get off of the trolley and view the gingerbread houses - AND take your own picture with Santa!
- The Pittsburgh Crèche - the only authorized replica of the 64 foot wide nativity scene in Saint Peter's Basilica in Rome
Join us for a fun, family-friendly holiday outing! All tours begin in the North Shore next to the Fred Rogers Memorial Statue (Tribute to Children) - between the river and Acrisure Stadium.
The Trolleys
Our gorgeous fleet of 1920s-style trolleys offer panoramic windows, authentic woodwork, and detailing reminiscent of the streetcars that once were a staple of transportation in the City of Pittsburgh. While you’ll step back in time when you step inside one of our trolleys, you’ll also enjoy the modern amenities of air-conditioning, heating, and custom audio for a comfortable and exciting experience.
We take great care to keep our trolleys in pristine condition and maintain all of the details that make a Pittsburgh trolley car experience so special!
Helpful policies
- All people in your party must check-in 15 minutes prior to your tour time. We cannot hold a tour for guests running late.
- We love all furry friends, but out of courtesy for all riders, Molly’s Trolleys Pittsburgh only allows service animals on board our trolleys.
- Guests are not permitted to bring food or drink items on board on our public sightseeing tours.
Adventure Tips
Arrive Early for Seating
The Jolly Trolley fills quickly during weekends; arrive at least 15 minutes before departure to secure a good spot.
Dress Warmly
The vintage trolley can be cool inside during winter months, so layer up to stay comfortable throughout the ride.
Bring a Camera
Prepare to snap photos of iconic landmarks draped in festive lights along the Three Rivers Heritage Trail.
Check Weather Forecast
Inclement weather could affect trolley operations; confirm tours are running ahead of your visit.
Local Insights
Wildlife
- Urban squirrels commonly seen near the river trail
- Migratory birds that flock near the city’s rivers in winter
History
The Three Rivers Heritage Trail follows historic riverfront paths used for trade and transport, connecting modern Pittsburgh with its industrial past.
Conservation
Efforts to keep the trail clean and sustainable help preserve Pittsburgh’s river ecosystems and urban green spaces during increased holiday foot traffic.
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Adventure Hotspots in Pittsburgh
Frequently Asked Questions
Recommended Gear
Warm Jacket
Keeps you cozy during the chilly winter trolley ride.
winter specific
Camera or Smartphone
For capturing festive decorations and memorable moments.
Comfortable Footwear
Helpful for boarding and disembarking the trolley safely.
Reusable Water Bottle
Stay hydrated, especially with kids along for the ride.