Independent Day School Trails

Fearless Hiking
Independent Day School Trails, Middlefield
December 2025

Note: Don’t walk trails at schools while school is in session. I walked these trails on a Saturday between Christmas and New Year’s Day.

This trail network was mentioned to me by a Middlefield resident in one of those, “oh yeah, bet you didn’t know about this trail, Mr. KnowItAll” messages. In this case, he was wrong. I was aware of this trail network, but like a few other similar trails I’m aware of, I decided I’d leave it off my itinerary because the Independent Day School is a private school for young kids.

“It’s actually open to the public during non-school hours,” I was told.

I poked around and that did seem to be the case, but I wanted to be sure I’d be on the right side of things so I visited when I knew the school would be on holiday break. Before going any further, I can tell you that while these trails serve a great purpose and I love that they exist, there’s no reason for any of you to go here.

The Independent Day School (IDS) seems like a pretty cool little place. Their whole thing, at least in the 2020’s, is “fearless learning.” This teaches students – from their 3-year old Beginners to the 8th graders – how to “confidently take risks, stretch beyond their comfort zone, and think independently in pursuit of joyful learning.” They focus on inquiry, creativity, and innovation. I support all of that.

And I support an on campus nature trail. And yurts. I support yurts too.

The yurt is an outdoor classroom of sorts and stands near the trailhead and is named in memory for a former student. I entered the trail through a gateway of sorts and began encircling the pond. This trail is called the Discovery Trail and I began on what a student-made sign told me is “Maple Alley.” There’s also a non-student made sign here explaining that this was Wangunk native land and that the IDS will honor the memory of the long gone Wangunks and treat the land as they would.

So instead of just building a (very necessary) boardwalk here, the school worked with the town of Middlefield and the state DEEP to do it right, since Sisson Pond here is part of the watershed for the Laurel Brook Reservoir. This was all done around 2012-2013 or so, after the trail fell into disuse and became an overgrown mess. I’m sure the students are happy that an effort was made to clean it up and it was reopened in 2014.

They did a great job with the boardwalk. I always feel bad at these places with massive boardwalk structures. Sure, they look great for about 10 years but then they became a huge hassle to maintain. You just don’t see too many boardwalks hiking the Appalachian Trail from Georgia to Maine for obvious reasons.

But this one is pretty nice.

I walked around the little pond and was mildly surprised to see there were more trails once I’d completed the loop. Several more trails, actually. Which is great; it means the students here have access to wetlands, a pond environment, and a New England hardwood forest. Different ecosystems to study all in their backyard.

Furthermore, it appears the school has a mountain biking club or something, as at least one trail here is obviously for them. And perhaps there’s a woodshop program that works with the biology department and the bikers to make the signs and ramps and berms and such. IDS seems like a right lovely place for kids to attend.

I poked around the trails away from the pond and was quite impressed with the maintenance efforts through “Grapevine Grove.” Tons of invasives and problematic plants hugged the trail including, yes, wild grapevines. The air, even in December, smelled of grape… and I kind of loved it. After finding myself on a mountain biking trail, I decided to find my way back to the playground and ultimately my car.

Google will suggest these trails are open to the public and even the school’s trail guide infers as much. I still don’t necessarily recommend popping down here to walk them, however, unless you go on a day like I did – when I was 100% certain there would be no one there. You just can’t be too paranoid these days.

Well done Independent Day School. From this Fearless Hiker to you Fealess Learners (and teachers), keep it up.

Independent Day School
CTMQ’s Middlefield Town Trails