Historic Trolley Rides

Take a trip back in time and ride the Delaware Water Gap trolley once again!

Pocono Daytripper’s elegantly restored trolley harkens back to a bygone era with authentic interiors, turn-of-the-century design, and the music of Fred Waring and the Pennsylvanians flowing from the loudspeakers. Your ride down memory lane is delivered in open-air comfort as you visit the quaint town of Delaware Water Gap, the Delaware Water Gap National Recreation Area, and surrounding areas.

John Whipple
John Whipple
To start off were picked up and dropped off at our resort, which was wonderful. The tour was a worth every penny! We saw so many things that we would not have been able to see had we been on our own. Pete is a great tour guide with a great sense of humor. He and Clyde, our bus driver, were very informative, entertaining and they were very personable.
Aaron Overton
Aaron Overton
The trip covered every major tourist destination you can think of, BUT also included many spots that are not so well known but very interesting. The tour guide knows the best food and dessert shops along the way and there was plenty of time to enjoy a snack. The level of historical knowledge and trivia games along the way was a major delight. The tour was worth every penny. My friends and I were more than thrilled with the experience and results of the tour. The tour guide and the bus driver are more than friendly and very accommodating to flexible itineraries. Your input can determine how the trip operates. It was a great time.
Candace Delanoy
Candace Delanoy
Our family of 6 took a day trip to New York City with Peter. It was fabulous!! We got to see so many of the major sites in just one day. We learned about NYC and the history of many of the locations. Things came up and Peter adjusted our schedule flawlessly and without any stress. The driver did an awesome job of getting us where we needed to be safely. Be prepared for walking for miles, but it is well worth it, and there are many times to take a break and rest. Peter takes great care of everyone and is flexible and friendly. Definitely the best part of our vacation!!
Lyndsey C
Lyndsey C
Not only did he take us on a great trip around New York! He also gave us great tips to do on other days! Because of him, we were able to see everything in New York! We also went to Philly and saw some amazing things because of his tips! We were able to see two waterfalls close to our hotel because of what he recommended. Without Peter, our trip would have been so boring! Thanks again for everything!
Rebecca Rees
Rebecca Rees
Wow! Peter and his team went above and beyond to not only get our guests safely to and from our venue but to do so in style! We had a complicated route to pick up guests and they handled it flawlessly, even in subpar weather conditions. We would recommend this service to anyone looking for a fun and unique transportation option. Our guests kept telling us how cool it was to arrive to the venue in a trolley! Thank you, Peter. You were awesome and we can't thank you enough for being a part of our day!
Desiree Frame
Desiree Frame
We had a wonderful time learning about the history of the Poconos and the Delaware Water Gap with our tour guide Peter. He was very informative (not just with history, but also local shops and restaurants to try out) and also enthusiastic enough to keep our young boys interested and engaged! Highly recommend taking this family tour.
Sara Talley
Sara Talley
We had the absolute best day with Pocono Day Tripper! We celebrated our best friend’s bachelorette with 3 great wineries. Peter coordinated the whole day, picking us up at our airbnb and making sure we had plenty of time at each place. This weekend was so special to all of us thank you Peter and the Pocono day tripper team for making it all happen!
Nancy Fowler
Nancy Fowler
My husband and I booked a trolley with Pocono Daytripper, wine tour, but since we were the only two people that booked for the day, we got a personal tour with the owner Peter. We visited two local wineries, a distillery and a venue that specialized in hard cider. Peter was awesome and was so friendly. We interacted so well, he made us feel like we had been friends for years! Thanks for making our weekend getaway extra special!! Love Nancy and Matt
Points of Interest
  • Historic Castle Inn
  • Legendary Deer Head Inn
  • Point of Gap Overlook
  • Cold Air Cave
  • Village of Shawnee
  • And more!

Mid-week and Weekend dates available from April to November

  • $30 per ADULT
  • $27.50 for SENIORS
  • $27.50 for Active Service Military
  • $25 per child, under 12
  • Children 2 and under free
Reserve your spot by 6PM the day prior to your tour for best availability.

The Historic Castle Inn, 20 Delaware Avenue, Delaware Water Gap, PA 18327

Book Online Now
Or purchase tickets at the Historic Castle Inn
20 Delaware Avenue,
Delaware Water Gap, PA 18327