A Portland Pilgrimage
- Jill McMahon
- 5 hours ago
- 4 min read

Last Wednesday, our kids left for a trip to Quebec City with their uncle and cousins, and they wouldn’t be back until Sunday. In 18 years of parenting, Tim and I had never had the house to ourselves for five days. I’m pretty sure the longest kid-free stretch we’d ever had was two. As much as we enjoy our boys, this felt like a huge gift...and we were giddy about it.
We spent the first few days together, enjoying things like reading books at the beach, not cooking, and leaning in to our responsibility-free lifestyle. Then for our final day, we decided to each do the thing that lights us up: pottery for Tim and hiking for me.
But as Sunday morning approached, I couldn't motivate to plan a hike. I didn't feel like a long drive, or a full day away. I'd fully settled in to enjoying our home, especially since it was clean and organized - the first thing I did on Wednesday when our two tornadoes left the premises.
As I considered my options, I remembered something my friend Dory had told me about a few months back. For her birthday, she'd hiked Portland's Forest City Trail - a 10-mile route across woods and neighborhoods, featuring 9 trails, school campuses, several parks, an historic cemetery, and two waterfalls. She'd split it into five sections: hiking one with each of her three kids, one with her husband, and one alone. I loved her creativity, her knack for finding adventure right at home, and I'd promptly added the trail to my own adventure bucket list. Sunday felt like the perfect day to check it off.
I wasn't up for the full 10 miles, so I decided to do half of it. I could reach the halfway point at Evergreen Cemetery with a short walk through Baxter Woods, which sat right behind our house - meaning this adventure would literally start from our backyard. From there, I'd head north on the Forest City Trail, ending at one of my favorite places: the Presumpscot River Preserve.
Since I'd only be gone a couple of hours, all I needed was a small pack with water and a light snack. I left the house at 7:00 a.m. and stepped onto the trail behind Tim's studio. The morning light was gorgeous, and I felt a surprising rush of adventure - this was a trail I'd walked a thousand times, but I'd never thru-hiked it all the way to Presumpscot Falls. I'd always driven there before. For years, I'd listened to mountain bikers talk about riding across town to the Presumpscot River on trails I couldn't picture, without really understanding how they got there or where these secret paths were. Now I was about to find out.
I had a paper map and All Trails GPS on my phone, but mostly I chose to follow the breadcrumbs of Portland Trails signs that kept appearing - on streetlights at intersections, school entrances, and quiet trails in residential neighborhoods - because that was more fun. Thanks to the great team at Portland Trails, there were signs everywhere.
The best part of my journey was running into all kinds of people I knew: UPS Pete, Gwen the golden retriever's owner Julie, my friend Kerry, and other friendly faces along the way. My friend Anna and her dog Flora (Romy's sister) met me at the final destination, and we walked another two miles together to Presumpscot Falls. Anna drove me back home and I returned nourished from time on the trail, and more in love with Portland than ever before.

Here's my challenge to you: wherever you live, find an adventure you can start from your front door. Explore the trails near your home - you may be surprised by the neighborhood routes you never knew existed, the way I was on Sunday. There's beauty everywhere, whether you live in a city with window-box flowers and pocket parks, or in the countryside with fields of wildflowers. The key is to embrace your surroundings and find nature wherever you are.
I called this hike my Portland Pilgrimage for two reasons:
1. I love alliterations, so "pilgrimage" worked better than "walkabout."
2. The definition of pilgrimage - a spiritual journey on foot to a sacred, holy place - felt true to my experience. For me, Portland is that sacred place, with it's diverse landscape and people: forests, waterfalls, art and music, coffee shops, bike paths, and the friends, family, and community I cherish. I love this city with all my heart, and they'll have to drag my dead body out of here, because I'm never leaving. In fact, I'd like my ashes spread over Presumpscot Falls. To whoever ends up responsible for my ashes: you now have that in writing.
Many people journey to faraway places for inspiration and growth, and there's much to be gained from travel and exposure to other cultures and ways of being. But I'd argue there's equal value in exploring and truly discovering the place you call home - adventures that don't require a plane ticket, a dog sitter, or a drain on your bank account. Explorations that help you really know and understand your place of residence, with all its hidden treasures. Trips that leave you feeling more rooted to your community. These are the gifts of local adventures.
In the end, the pilgrimage from my house to Presumpscot River Preserve was 5.5 miles and 233 feet in elevation gain. Here a link to my route on All Trails if you live in Portland and want to try it. You could also hike the full 10-mile trek across town, that's next on my list. See you out there!
