Metroparks Trail Challenge: Menacing trees, meandering trails, a mysterious castle in North Chagrin

Erin O’Brien has accepted the Cleveland Metroparks 2022 Trail Challenge. She will be chronicling her adventures on the trails throughout the year.

On Oct. 8, my dearly beloved and I stepped out for my ninth installment on the Metroparks 2022 Trail Challenge Presented by Cigna. It was a positively dazzling fall day.

Now then, suppose a person—a person just trying to do her very best—somehow pulled up the 2021 Trail list instead of the 2022 Trail list (which, incidentally, look really similar), and opted for the North Chagrin Reservation challenge route, which includes a 4.2-mile route that “requires you to pay attention to the map and trail junctions.”

Those trails include the Castle Valley, NC2, Hemlock, and Squire's Lane Trails—all of which are reportedly “well marked.” I later discovered this was different from the 2022 route, which is essentially a 4.5-mile loop along the NC2 equestrian trail. Oops.

In the end, the two routes were pretty similar, but even so…. And if that failure wasn't enough personal disclosure for one article, here comes another: I had never been to Squire's Castle before this hike. There, I said it.

We remedied that unfortunate life omission by starting our trek at the storied local landmark, which is every bit as cool as you think it's going to be. I only wish there was more of it. That said, what's left of the structure is fascinating and fun and a little bit spooky in its own way.

If it is not haunted, it should be.

Instead of detailing the Castle's strange history here, I invite the reader to hop over to Cleveland Historical and read Chris Roy's economic yet thorough listing about the Northeast Ohio relic. Yes, Standard Oil bigwig Feargus B. Squire built the joint on his 525-acre “River Farm Estate” circa 1897. No, he never lived in it full time. Yes, it looks like a little castle, but was really designed as a gatehouse.

After poking around the Castle, we made our way along the designated trails, but not without some difficulty.

“I can't tell if we're still on a trail.”

“Wait … were we supposed to turn back there?”

“We haven't passed a marker for a long time.”

<span class="content-image-text">Just a simple tree or sinister sign post? Only the Blair Witch knows for sure</span>Just a simple tree or sinister sign post? Only the Blair Witch knows for sureIf the Blair Witch wasn't dogging us, dear reader, it certainly felt like it. A perfectly round hole in the ground belied an unseen network of tunnels for her minions to scurry around unseen, unless it was (eek!) a peephole.

Weird trees curved at unnatural angles like evil signposts. Tangled roots threatened to disengage from the earth and wrap around our ankles, while others splayed out from their uprooted hosts like freakish woodland creatures poised to spring into attack at any minute. And at least one Google Map image proves people have been known to partially disappear in these woods!

Lastly, fellow adventurists, in the center of small clearing sat an elaborate stone fireplace and tall chimney amputated from any surrounding structure that might give it context. We stopped and blinked before the curious hearth, wondering if a cauldron would fit in it, but not for long. We quietly backed away and moved on.

For those not under a witch's spell, this hike is utterly glorious, with mostly natural surface trails that feature a host of rustic stairs and walkways, some of which are very well worn. There is also one significant hill that had us pumping air when we got to the top. Other than that, it was fairly easy-going, perfect for grade-school aged kids on up.

And it was gorgeous, with sunlight dappling the autumn leaves as the path wound around the rim of the Buttermilk Falls Creek ravine (regrettably, we did not take the short walk over to Buttermilk Falls, but you should).

By the time we got back to Squire's Castle, my iPhone said we'd walked a full two miles more than the trail list had indicated.

<span class="content-image-text">On the trail in the North Chagrin Reservation</span>On the trail in the North Chagrin ReservationToo many wrong turns? The Witch? A wiggy iPhone? Who knows, but the most confounding detail of the day was the sky-high heels worn by the otherwise beautiful brides and their myriad maids as they teetered around the expansive lawn in front of the castle for photo shoots, which were happening all around the stone structure. In addition to the weddings, at least one of them featured some sort of medieval re-enactment complete with swords.

We did not have any swords—or high heels, having opted for big, ugly, and (most importantly) sturdy hiking boots instead. Nonetheless, we felt completely at home amid this magical and mystical park with its endless tricks. As for treats, there were none to be found.

Unless of course, a person decided to dive into the Halloween candy a little early. After all, completing this challenge will surely earn you a fun-size KitKat or two.

Some takeaways:

• Squire's Castle hasn't always been a mecca for blushing brides and their entourages. Back in the1960s, it was reportedly a popular hangout for motorcycle gangs and vandals.

• If you care to navigate the Google machine, details about the Squire family go on and on, and are sometimes contradictory. Was Feargus's wife named Rebecca or Louisa? Did she die of a stroke or pneumonia? Or did she "stumble accidentally into a looped rope and hang herself?" Hmm... looks like the internet is as confused over this as I am.

• Per his obituary in the July 21, 1932 “Plain Dealer,” Mr. Squire “made two trips around the world” after retiring. The article offered no further details.

• Add another dimension to your visit on the Castles and Camps hike. Metroparks Historian Judy MacKeigan will lead the group on a 2.5-mile trek from Squire’s Castle to the site of an old YMCA camp on November 19 at 3:30 p.m. Free and open to the public.

Squires Castle is at 2844 River Rd, Willoughby Hills, in the North Chagrin Reservation.

Erin O'Brien
Erin O'Brien

About the Author: Erin O'Brien

Erin O'Brien's eclectic features and essays have appeared in the New York Times, the Los Angeles Times, the Cleveland Plain Dealer and others. The sixth generation northeast Ohioan is also author of The Irish Hungarian Guide to the Domestic Arts. Visit for complete profile information.