A Wenakeening Woods Trek

Story and Photos from Tommy Zazulak

I’m lost. I admit it. Been stumbling around the Wenakeening Woods inside the Upper Charles Conservancy for the past two hours and I still have no clue where I am.

When I started this adventure into the forest, I had been standing on the sandy gravel stone path better known as the Holliston Rail Trail. Brave hearted and full of bravado, I decided more was needed. More mud, more trees and  more daring. So I veered left off the Holliston Rail Trail and into the spiny, tree root littered path that ushered me into the Wenakeening Woods.

Studies in biology and anthropology will tell you Mother Nature likes to drop subtle hints when your cozy and domesticated life is about to be grossly interrupted by her majesty. A clap of thunder? Oh, it’s gonna rain. Thank you Mother Nature, allow me to return inside where I won’t get wet. An animal growls and bears its teeth. Oh, I’m about to be attacked by a rabid predator. Thank you Mother Nature, allow me to turn around and run the other way so as not to become an appetizer to a hungry coyote.

When I stepped off the Holliston Rail Trail and into the Wenakeening Woods, Mother Nature gave no hints that my stable Facebook-Snap Chat-Instagram-world was about to be held in temporary suspension. It was probably the same anxiety the Donner Party felt when the leader said “fear not brave souls, we can make it over these hills!”Anybody hungry for BBQ?

It was the silence in the Wenakeening Woods that should have told me everything was about to go wrong.

There are four marked paths in the Wenakeening Woods: red, yellow, blue and a hybrid path marked both yellow and blue.

And so I’m now on my third lap and second hour of the hybrid trail and I have no idea how to get home. I’ll confess a small bit of panic has set-in. Most wilderness trails have maps within the trails posted for all to see that outline the routes. Always on these maps is a big star that indicates “YOU ARE HERE.” 

In the Wenakeening Woods there are no such maps. And it’s been a great while since I’ve seen another hiker. I’m hoping a mountain biker with a bike-mounted GPS installed smart phone will approach and I can ask for directions.

I decided I’d play it cool if such a biker approaches. I’ll just be like “Hey nice bike! You ride well! By the way, where the holy Hell are we? Better still, how do I get home!” But no such bikers have approached.

I do know this–when I entered Wenakeening Woods, I entered from the yellow trail. So that’s what I need to find. I see markings ahead for the red trail. No, that won’t help. Still walking. I see markings for just the blue trail. No, that won’t help either. Then a split marking! Two little upside-down “L’s”, one colored blue (not that way) and one colored yellow.

I followed the yellow “L” which ultimately led me to the solid yellow trail and then, finally, to a small rest stop and wooden bench. I wanted to sit but feared breaking the bench under my weight. The bench looked as if it had been resting there since the time of Moses and the great flood. And so I pressed on, finally exiting the woods.

The feeling of relief was overwhelming–like the Hobbits as they exited the Mines of Moria. Only this was real, and I’m too tall to be a Hobbit.

The Publishers


  1. Dave Bastille on May 14, 2020 at 2:27 pm

    I’d like to recommend an app with an odd name, onX Offroad. I’m not an app guy but I dislike getting lost in the woods; it takes the fun out of it. The basic app is free. It shows most of the trails, and where you are on them.

  2. Marc Connelly on May 14, 2020 at 9:53 pm

    Ok , rather than have you eating worms or loved ones while lost in the badlands of Holliston, try this.
    Go to the town of Holliston website. Search for Conservation Commission. When that site comes up you will also see Conservation Associates. Click on that. You will see a few possibilities but click on maps. We have many of the trails for Conservation land available and you can print them out. A real map works long after a cell phone has died! Good luck.

    • Tommy Zazulak (the author) on May 15, 2020 at 8:33 am

      Thanks Marc! Saves me the ghastly task of eating my left foot next time I’m in Wenakeening Woods

  3. Richard Shansky on May 15, 2020 at 7:43 am

    Your mistake was not taking a picture of the trail map when you entered at the Rail Trail. I know, the map is not very good (hard to distinguish yellow from red) but it’s better than nothing. did you bring a cell phone with a camera function?

    Also, most wilderness trail do NOT have regularly posted maps with “You are here” indications. Only a few (e.g. some Trustees properties) have the resources for such a luxury. Whenever you go into the woods, you must be prepared with a map and the essentials such as water, a snack, a cell phone, a rain jacket etc.

    • Tommy Zazulak (the author) on May 15, 2020 at 8:58 pm

      Thanks for your insights Richard. I made a lot of mistakes on this adventure and those missteps are what made the trek, for me, so interesting albeit a bit fear-laden. I’m not an experienced hiker and won’t pretend to be.

      I just didn’t expect the Wenakeening Woods to be as expansive as they were. When I saw the sign for the Wenakeening Woods entrance on the Holliston Rail Trail, I just thought “oh here’s a nice little woodsy trail, this should be fun”. And oh how wrong I was. At one point during the walk, as I was floundering around trying to regain my bearings and find my way home, I discovered a beaver dam and beaver lodge in an enormous reservoir in the middle of the Woods. It was stunning. When I got home, I Googled “beavers in Holliston” only to learn that, as recently as 2015, Holliston has been home to a considerable beaver colony. Again, amazing!

      On my next visit into the Woods, I will definitely do as you advise and bring a map and some of the items you suggested as I very much enjoyed the journey.

      Cheers mates, see you on the other side….

  4. Chris Keys on May 15, 2020 at 7:45 am

    Wenakeening Woods is beautiful, a real get-away right here in Holliston.

    You can use AllTrails as a free app and track your position against an overlay of the trails. Here’s an image from that app : https://1drv.ms/u/s!AruNxo9xlgD2gYNoJgehm6gG1gfoTg

    If you‘re somewhere without a trail map but have a signal, drop a pin, walk 10 mins, drop another pin, and then see which direction you are headed. In this case you could navigate according to both the rail trail and Mission Springs – both show clearly on Google Maps for example.

    Hope you don’t give up on Wenakeening Woods!

    • Tommy Zazulak (the author) on May 15, 2020 at 9:12 pm

      Hey Chris, thanks for your help.

      I have an iPhone but don’t really know how to use it beyond talking, texting and taking pics. How do you ‘drop a pin’? And in fact what is “dropping a pin”? Is that possibly establishing a point of reference with the phone?

      Please forgive me and bear with me. I’m an old guy who remembers the days of MS DOS, floppy disks, Atari and the Commodore 64 computer. The first video game I played was “Pong” and I remember when cell-phones were enormous bulky devices in backpacks with black cords. I also remember when disco was cool but that’s perhaps a story for another forum.

      Thanks for your insights, mate!

  5. John Passier on May 17, 2020 at 8:04 am

    Funny article. There’re trails that lead to Idlybrook in Medway. I run in these trails a lot. Below is a good trail map.


    • Tommy Zazulak on May 18, 2020 at 9:44 am

      Thanks John!

      I love that section of the trail too. The Idylbrook & Medway portions are beautiful, postcard perfect.

      Keep well & see you in the jungles – well maybe not the jungles, let’s stay to the Woods.

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