5:12 min April 08, 2024

Downtown Stroudsburg Walking Tours

Step back in time during seasonal walking tours returning to downtown Stroudsburg through the Monroe County Historical Association!

Meet Dan McSweeney, our tour guide for the day. He brings us to the former Stroudsburg National Bank on Main Street, known today for its clock tower. The bank's original board of directors included railroad tycoon Jay Gould. Look closely toward the second floor windows and you'll spot intricate faces carved into the stone.

PTN’s Brianna Strunk commented, “it’s amazing when you're walking versus driving, you can take a look at all the details, things you wouldn't notice when whizzing by really quick.” Dan responded, “absolutely, I’ve noticed so many different facts and details.”

We also swung by the Stroud Mansion, the former home of John then his brother Daniel Stroud, whose father founded Stroudsburg. “This old house, a beautiful house, has a lot of historical significance and is an icon of Stroudsburg,” McSweeney noted.

In 1920, the building was saved from demolition and is now home to the Monroe County Historical Association. While a Heritage Center is being constructed behind the Stroud Mansion, the Monroe County Historical Association and its historic walking tours are operating from a temporary location further down Main Street.

“We wanted to be sure that we were still fulfilling our mission to bring educational opportunities to the public, and this was something that was on our ‘to do list’ for a while. So, this was a great opportunity to introduce walking tours of downtown Stroudsburg, and they have become very popular,” explained Amy Leiser, MCHA executive director.

Tours are offered every Tuesday, Wednesday, and Thursday, spring through fall, and have attracted people from all over the country. No tour is ever the same, since each guide brings their own personalization. Dan, who now splits his time between New York City and the Poconos, loves sprinkling in his childhood memories from Stroudsburg.

“Right here, there used to be all single car garages, probably about ten in a row. We used to jump from roof to roof on those little garages,” he pointed out during one stop.

Next, we walk through Stroudsburg’s historic district, which includes the former home of A. Mitchell Palmer, a controversial national figure who served as United States Attorney General under President Woodrow Wilson.

“Palmer is the person that first hired J. Edgar Hoover to be the first director of what was called the Federal Bureau of Investigation, now known as the FBI,” McSweeney explained.

Not far from there, this is where Monroe County's first female doctor lived and practiced during the late 1800s and early 1900s. Phoebe Palmer Flagler Hagenbuch lived to be 95.

“She was a groundbreaking woman for obvious reasons, and a lot of people feel she was innovative in her approach to treating her patients,” McSweeney added.

Dan also took us to a building PTN’s Brianna Strunk remembers very well as the former School of Cosmetology, where she had her 10th birthday party. But before the glitz and glamor of a cosmetology school... “this was built in 1866 as the original vinegar works, where they manufactured vinegar. In addition, it was the first place in Stroudsburg where they would hold public meetings,” McSweeney said.

You'll also hear about The Old Jail in Courthouse Square, which housed prisoners for over a century. Today, Courthouse Square is the backdrop for community events and home to charming small businesses, such as Tolino Vineyards.

“The land was donated for public use by the woman who lived in this house here, Sarah. She was one of the daughters of Jacob Stroud,” McSweeney showed.

From iconic buildings to lesser known landmarks, the tour around this small town promises big stories about Stroudsburg’s rich history. Each step forward, taking you further back in time.

“We’re really encouraging people to spend the day in downtown Stroudsburg. Come for lunch, shop at some of the shops, take a walking tour. We have 400 years of styles of architecture right along Main Street, from the Stroud Mansion from the 1700s up to new construction just built a couple years ago. It’s really neat to see all the styles,” Leiser explained.

That's just a sneak peak of all you'll learn on the tour. Reservations are strongly encouraged. You can find more information about tour times and pricing, plus a brochure for a self-guided tour you can take any time, at