Riding the Berkshires
“Uphill fast, downhill slow, on the level let ‘em go”
Photographs by Donna DeMari
Many of my favorite riding trails were once remote logging routes, two-track dirt roads that led horse-drawn carts from one verdant valley—up and over a ridge—down to another open spread of farmland. I imagine that these woods are still similar to the way they were over a hundred years ago, awesome and quiet, like nature’s chapel, flickering with bird song and filtered light. My trusty Missouri Foxtrotter, Barranca, always seems to know where he’s going as if it were a primal instinct. A horse’s memory is profound.
Riding with Johnny Snyder is truly an adventure. He is usually dressed to the nines in some rock-star outfit and ready to go. One day we were invited to explore a property in West Stockbridge, and as we climbed the steep trails, we suddenly found ourselves in a fairyland of blooming mountain laurel. I had never seen such a display.
Johnny is new to the sport, but already he has taken to galloping his horse, Cowboy, barefoot, bareback and bitless. Far surpassing the average novice, he never turns down an invitation to push his limits, whether it is a local fox hunt or a polo match. Sometimes I wonder why a world-class expedition leader is content to ride with me.
But we do share a sense of adventure, and are always on exploration alert. We both love riding up mountain trails at a fast-paced gallop, maneuvering through an obstacle course of low-hanging branches, fording streams, the sky bright blue, the height of summer—it doesn’t get much better than this.
Having a two-horse trailer, I am able to drive all over the county to various trailheads. Berkshire Natural Resources Council has preserved a wonderful loop called “Alford Springs,” far from any distraction. I wonder why there aren’t more people out exploring these places. For the most part, we are alone. Imagine cantering through old growth forests with mountain runoff trickling down, following paths along ridge-tops, stopping to take in a distant view of unspoiled rolling hills.
I have learned a bit more about the forest flora from riding friends—where ripe elderberries can be harvested and made into a delicious, subtle jelly. Along some of these paths, an abundance of sweet fern grows. Crushed in your hands, it releases a subtle peppermint smell, and when the blackberries are ripe at the end of summer, we often swipe a handful as we ride on by, quenching our thirst.
There are also other natural wonders I’ve come upon while riding—a nest with 12 wild turkey eggs, a newborn fawn curled up in the tall grass, a glistening bear cub on the run, the swivel head of a barn owl peering down, and one time, I believe I saw a large grey wolf close to where I had parked my trailer. Still loaded, my horses went crazy—its smell must have been alarming.
Following well-worn tractor tracks, we stay clear of the cultivated field of corn up on Baldwin Hill, an elevated stretch of unconfined space, where field yields to open field, and hedgerows are filled with the scent of wild rose, a full view of our majestic mountains beyond. Up here on the hill, I sink into the rhythm of my horse and become more in touch with my instinctive self, more alert to my surroundings. At the right time of year, you can witness birds in migration—wheeling flocks burst in the sky above like opening chrysanthemums, swooping into ever-changing forms.
Once you know a trail well, you can ride with ease—you know where that rusted out culvert is, where a deep hole has been marked with a stick. You know which paths are blocked by massive fallen trees, or where the ground becomes too muddy to traverse. Any sign of a mood is swept away and you are lifted into another realm. After an hour in the saddle, you feel rejuvenated, cleared, ready for anything.
In Great Barrington, it takes just minutes to leave the backed-up traffic on Main Street. Hayley Road leads to a path that rambles down to the falling waters of the Green River. On a hot summer day, the horses enjoy crossing the stream here, taking a drink, wading downriver and soothing their hooves.
The conservation property off of Hickory Hill is a wholly different destination. With its tall pine trees and needle-laden paths, it is refreshingly cool in summer. From these trails, wandering past the old lumber mill, we are soon out on the fields behind the Rudolf Steiner School. But as we attempt to find another access to the river, a local farmer comes zooming out across the land on his four-wheeler, startling the horses as he warns us off.
Johnny wants to ride to Wheatleigh someday for a champagne brunch, and I’m game, but for now we settle on a more down-home snack trip to the top of Mount Tom Ball, where the horses can also take a break, girths loosened. While Johnny takes a swig of Scotch from his silver flask, I gulp water from a plastic bottle. From up here in the pines, we can look down onto the Alford Valley with its distant barns and meandering brook, and feel like we are a million miles away. I gaze out as far as New York State and scan the various areas where I have ridden, feeling an intimate connection to this landscape, not because I’ve driven past it, but because I have ridden over it.
Having explored the Berkshires on horseback for over 30 years, I have to admit that some things have changed. At one point I wanted to start a “Save the Dirt Roads Society,” for most of the old dirt roads were being paved, and many new homes were going up on agricultural land. Some newcomers are horse-friendly, but others are wary. Still, there are many country-minded folks who give us permission to ride over their properties, and for their generosity of spirit I am continually grateful.
Taking in our wide-ranging Berkshire land on horseback is akin to a moving meditation. Witnessing life as it passes always makes me want to enter the moment, and what better way to do that than riding out into nature, out into the elements, breathing in the forest air. Even if there are risks, they are well worth taking, for mishaps are few, and the benefits and joys of riding are always abundant.
An Equine’s Perspective
Plenty of locations are available to learn how to ride or to spend time exploring the Berkshire landscape. Here are some:
- Aspinwall Equestrian Center offers Berkshire Horseback Adventures from one hour to half a day to overnight; 293 Main St., Lenox; 413-637-4894
- Bellwether Stables has lessons, boarding, a summer riding program, and student horse shows; 136 Old Richmond Rd., Pittsfield; 413-717-2433
- Blue Rider Stables has lessons and workshops for children and adults, and a therapeutic riding program for people with disabilities; 15 Farm Ln., South Egremont; 413-528-5299
- Blythewood Stables offers lessons and training, horses for sale or lease, and horse shows and clinics; 382 Churchill St., Pittsfield; 413-499-7964
- Harmony Hill is a quality horse show barn with horses for sale, and a sister barn in Florida; 138A Seekonk Cross Rd., Great Barrington; 413-528-4034
- Undermountain Farm gives lessons, pony rides, and offers horse boarding; 400 Under Mountain Rd., Lenox; 413-637-3365;