By Jane Larkworthy
Illustration by Molly De St Andre / Moho Design Creative
I first visited the Berkshires when I was in my thirties. A friend invited us to her parents’ weekend home just over the border in Canaan, New York, and we’d spend the annual weekend going to Tanglewood, gathering dinner groceries at Guido’s, and maybe throwing in a visit to the Lee outlets. Often, our host would also plan a hike. Equally as often, I would roll my eyes. Hiking? Boring. Not that I preferred heading out and running miles on a bucolic country road or Googling the nearest gym. No, I’ve always been preternaturally lazy, but I also happened to view hiking as an activity that grandparents and bird watchers did. No offense to octogenarians or ornithologists, but I was neither, so driving to a trailhead and following a path determined by swipes of paint or tiny yellow buttons on trees seemed as interesting to me as wearing Birkenstocks. Ah, stupid, naive, close-minded younger me.
I currently own more pairs of Birkenstocks than I can count on one hand, and I sometimes even wear them when I hike if I know the one I’ll be embarking on is easy, flat, and dry (my preferred kind of hike. Did I mention my sloth leanings?). It took a visit to Mexico’s Rancho La Puerta for the hiking gods to bestow their magic upon me. Nestled against a mountain range that isn’t too unlike the Berkshires (except their hills are tree-less), I spent the first day or two begrudgingly keeping up with my pack as we climbed and climbed, reminding myself that a massage or facial (my preferred spa activities) were the subsequent reward.
I didn’t expect to sweat so much. I loved how clear my mind felt afterwards. Hikes might make you one with nature but they also make you one with your thoughts. You can sort things out on a hike, assess issues more clearly, work out solutions, and devise plans. When my husband and I hike, the conversation is usually the dinner plan and what TV show to watch next. Hiking solo, however, I’ll find myself playing out a conversation with someone I might be in conflict with. More fun, I’ll belt out a tune or two. My friend Holly takes a more chill approach. “I’ll stop to look at the view—the trees, a rock, the path, the clouds,” she said. “I drink it in, while connecting with how being outside has felt since childhood.” Being outside. Shouldn’t we be outside more?
Every time I mention to anyone that we’re avid hikers, a chest-pounding timbre weaves through my voice, as if to say, Aren’t I the healthy athlete? Truth be told, my hikes are more like walks—they just happen to be on dirt or grass, with the occasional sections of rocky obstacles. But they get us out there, get our hearts racing, and might even get a bit of sweat running down the back. And we pat ourselves on those sweaty backs because we gave our bodies what they needed. Even some singing.
Favorite Hikes
(but please don’t share)
Excellent Views
Monument Mountain, Great Barrington. Tip: Park around the back (on Route 183) where it’s significantly less populated.
Higher Degree of Difficulty
Alford Springs, Alford. The Father Loop is 4.3 miles, offers a variety of topography, and has more uphill challenges than your first entry-level job.
Most Narnia Looking
New Marlboro Preserve, New Marlborough. With verdant pines and sweeping drops that flow down to various bodies of water, you’ll think you’re in New Zealand.
The Hidden Gem
Roaring Brook Trail, Williamstown. The only frustrating element of this trail is that, due to being off the beaten path, it can come with downed trees. Consider it nature’s obstacle course.
Gear to Go
Jane’s curated a list of her must-haves for your next day outdoors.
The Water Bottle You’ll Want
Forget the Stanley. Owala FreeSip Water Bottle is leakproof, comes in a variety of sizes for both backpack and car accommodations, and is available in an assortment of colors. owalalife.com
Dual Duty
On mercurial-weather days, REI Co-op Sahara Guide Convertible Pants turn into shorts with a quick unzipping. rei.com
Application Required
Sunscreen preferences are subjective, so find your favorite and be sure to use it liberally (but MD Solar Sciences Mineral Creme SPF 50 is a super luxurious formula). mdsolarsciences.com
Post-Hike Relief
Finally made it to the summit but your legs and back are resenting your zeal? Pour a packet of Nature of Things Fortifying Magnesium Soak into a hot bath and let the magnesium chloride and tangerine and lavender oil work their magic on your overworked limbs. Scout House, Great Barrington
Jane Larkworthy was a renowned beauty editor in New York City for decades—and, more recently, a renowned resident of the Berkshires, a friend, wife, stepmother, giver, and writer. She passed away from breast cancer on June 4, 2025. The B was fortunate to have Jane’s witty and engaging voice in her column, “On a Lark,” in most of our issues—she wrote about her love of hiking, gardening, Birkenstocks, and her dog, Remy, among other topics. She is missed.
