A Winter Workday in Westbrook

“But what do you do in the winter?”

This time of year, our three trail crew members hear this question a lot. Jaime, Daniel, and Gabe take care of the trails in every season — even when they’re covered in snow. The conditions this time of year make traditional trail work with wheelbarrows and rakes impossible. But what does a winter workday look like? As the Communications and Events Manager, I decided to find out and report back.

So last week, I pulled on my snow boots and joined Gabe, our Trail Stewardship Coordinator, for a morning on the trails.

8:15 a.m.

Gabe and I met at a public parking lot in downtown Westbrook so I could leave my car and hop in his truck. When I opened the passenger door to his forest green Toyota Tacoma, he handed me half a pastry. I knew it was going to be a good day.

8:30 a.m.

We arrived at our first stop of the day: Saccarappa Elementary School in Westbrook. In 2025, we built a trail through the woods behind the school to connect Saccarappa with nearby neighborhoods. Our task today was to shovel a path from the trail to the parking lot that would make it more usable for kids. Because of the snow, we could see how well-worn the trail was. Unfortunately for us, the trailhead was obscured behind a ten-foot mountain of snow that had been plowed in front of our trail.

We each grabbed a shovel from the back of the truck and started chipping away at the mountain. Kids had forged a new path over a short wooden fence bordering the parking lot to get to and from the trail, and we wanted to make the trail safer — and easier — for them to use.

After quite a bit of strategizing and sweat (“I’ve never shoveled over my head before,” I said at one point), we carved out a tunnel through the snow. I could imagine how much I would have loved it as a kid; I hoped the kids walking home on the trail that day were excited to find this new trail through the snow waiting for them.

The mountain in question

Success!

9:15 a.m.

Gabe shoveled the other end of the Saccarappa School Trail on Merganser St. Without a mountain to move, this took about two minutes.

9:30 a.m.

We arrived at our workshop in North Deering to sharpen Gabe’s chainsaw. Portland Trails has two workshops — one on Blueberry Dr. next to the Stroudwater River Trail, and one next to the new North Deering Park. Of the two, this one is nicer thanks to its concrete floors and electricity. (That might tell you a thing or two about our other workshop.) We loaded three wheelbarrows into Gabe’s truck to move to Blueberry Dr.

Look at those sparks!

10:15 a.m.

Next, we shoveled parts of the Westbrook Schools Trail to make street crossings easier to navigate. We cleared snow on Landing Rd. and Stroudwater Pl. And with that, we were finished shoveling for the day!

10:45 a.m.

Gabe led me on the site of a potential future trail through Saccarappa Cemetery to Beaver Pond. It was so serene that I almost forgot we were next to two busy main streets. This winter, Gabe is working on writing a proposal to the City of Westbrook to make this trail a reality.

11:00 a.m.

For our final project of the day, we headed to the Conant Trails to cut back some invasive plants. After we trudged through deep snow to get to the site, Gabe used his freshly sharpened chainsaw to cut down trees, and I used clippers to slice through the smaller stems. We cut the plants back until we hit our noon deadline. We each had meetings to attend — mine in person, his virtual from his truck — so we left the rest of the plants for another day.

12:10 p.m.

Gabe dropped me off back at my car where the day started. And that, my friends, is what a winter workday looks like.