Turrets & Trail: Hiking the Squire's Castle Loop in North Chagrin Reservation

Dan Wagner
2 days ago
4 min read

Hiking the Squire’s Castle Loop in North Chagrin Reservation is like stepping into a woodland fairy tale with a touch of history—while staying right in Cleveland’s backyard. The 2.6‑mile loop treats you to tall, shaded hardwoods and hemlocks, and a couple of pleasantly steep inclines at the start and end, with mostly level, well‑maintained paths between. The highlight, of course, is reaching the evocative sandstone shell of Squire’s Castle—an 1890s gatehouse ruin that’s open to wander through and perfect for photos or a laid‑back picnic on the grassy field in front.

Trailhead elevation 712'

Water none

Don't miss exploring the inside of Squire's Castle

Hiking the Squire's Castle Loop

I arrive at the trailhead around 8:00 a.m., and the parking lot is already close to full. The trailhead sits beside a large pavilion and restroom facility, tucked near the end of a sprawling field in front of Squire’s Castle. After downing a bottle of water, I set off for a quick run. The trail begins with a steep climb along the NC2 Bridle Trail, gaining about 125 feet in just the first 0.2 miles.

Thankfully, a dense canopy of hardwoods provides plenty of shade—a relief with the heat index pushing past 100 degrees. At the top of the hill, the yellow-blazed trail levels out and meanders quietly through the forest.

At 0.75 miles, I reach the blue-blazed Squire’s Lane Trail and veer left.

The next stretch rolls gently through a beautiful mix of hardwoods and mature hemlocks.

After a brief incline, the trail flattens again, and just past the 1.5-mile mark, I spot an unofficial trail veering right. I follow it about 100 feet to a small overlook and take a moment to enjoy the view.

Roughly 100 feet later, another user-created path leads about 150 feet to the foundation remains of an old structure—what it once was, I can’t say.

After a short stop, I return to the main trail as it winds deeper through the woods. Around 2.2 miles in, the trail begins to descend, reaching the back of Squire’s Castle at 2.4 miles.

I’ve visited the castle several times before, but today holds something special. As I walk through its arched interior, I witness a young man down on one knee, proposing to his girlfriend in front of an old fireplace. She says yes and breaks into tears. I stop to offer congratulations and take a photo of the newly engaged couple to help them capture the moment.

Built in the 1890s by Feargus B. Squire—vice president and general manager of Standard Oil—the structure was intended as a gatekeeper’s lodge for a much larger estate that was never completed. Though it looks like a quaint stone castle, it was only the first step in Squire’s vision for a 525-acre countryside retreat he planned to share with his wife, Rebecca.

Wealthy and somewhat reclusive, Squire emigrated from Exeter, England to Cleveland in 1860. After living in New York and Baltimore, he and his wife eventually returned to Cleveland, where Squire joined Standard Oil of Ohio in 1885 as co-manager alongside Frank Rockefeller, brother of John D. Rockefeller. A notable innovator, Squire is credited with designing the first tank wagon for transporting oil. The family initially lived on Cleveland's Prospect Avenue before relocating to a mansion on Millionaire’s Row along Euclid Avenue at East 78th Street.

Drawn to the natural beauty of the Chagrin Valley, Squire purchased 525 acres there in 1890 with grand ambitions of building an estate modeled after English and German baronial halls. The structure now known as Squire’s Castle was constructed as a gatehouse and caretaker’s residence—what the Encyclopedia of Cleveland History describes as “a picturesque castellated and turreted ruin.” Built from locally quarried silt stone, or Euclid bluestone, the building was only the first step in what Squire hoped would become his “River Farm Estate.”

He began transforming the land with tree plantings, roads, bridges, and ponds—one of which is now known as Sunset Pond, located nearly two miles from the Castle. But plans for a main residence were abandoned when Squire’s wife, Rebecca, expressed her distaste for rural life. Instead, he built a grand home called Cobblestone Garth in Wickliffe, where he later served as mayor.

In 1922, Squire sold the Chagrin Valley property to a private developer, and in 1925, it was acquired by the Metropolitan Park Board. This acquisition became a cornerstone of what would eventually become the North Chagrin Reservation of the Cleveland Metroparks. Around this time, the structure began to be referred to by locals as “Squire’s Castle.”

Though never a full-time residence, Squire often used the gatehouse as a weekend retreat, frequently accompanied by his daughter Irma rather than his wife. The interior was expansive and well-appointed, featuring multiple bedrooms, living spaces, a large kitchen, and a breakfast porch. His personal library—the western-most room—was filled with books, artwork, mementos, and hunting trophies. The rooms boasted white plaster walls, finely crafted woodwork, and leaded glass windows that looked out over the estate.

Several informational placards inside and around the castle share its history—details I take the time to read, finally learning more about the gatehouse I’ve visited so often but never truly explored. Afterward, I follow a short paved path that leads back to the parking lot, bringing the loop to a close.