New England

Guided Winter Adventures in New England

From snowshoeing rolling trails to riding horseback through the woods, let a professional guide show you the best of a New England winter.

By Yankee Magazine

Dec 20 2018


Summiting New England’s highest mountain might be the ultimate winter adventure, but it’s not to be undertaken lightly.

Photo Credit : Cait Bourgault
Whether you’re chasing a once-in-a-lifetime thrill or simply looking to get out of your recreational rut, let New England’s outdoor pros lead the way on these great guided winter adventures, plus more ways to enjoy the outdoors during the snowy months.

New England Guided Winter Adventures

A Maine Snowshoe EscapeSnowshoeing with Maine Huts & Trails in Kingfield, ME

Kimberly Truskowski
Snowshoeing Guide
Winter adventure she’d most like to try: “I’ve often hiked and camped in Baxter State Park, but I’ve never done backcountry skiing and winter camping there. That’s something I’ve been dreaming about for a long time.”
Maine Huts & Trails, Kingfield, ME
Photo Credit : John S. Dykes

Bundled in warm layers, snowshoes strapped to my feet, I am standing at the Stratton Brook Trailhead in Carrabassett Valley, Maine, on a Saturday morning with eight other people. I’ve just dropped off my backpack to be shuttled to a hut up in the mountains of western Maine, and Kimberly Truskowski—our genial, cool, colorful-headband-wearing guide—is painting a picture of what awaits us this weekend, on our Maine Huts & Trails snowshoeing trip.

“Maybe you’re here to escape from the chaos of life,” she says. “Or maybe you’re here to connect with the natural environment. Either way, it’s winter’s art out there, like walking through black-and-white photography provided by Mother Nature.”

We are all strangers—the only thing we know about one another is that we all signed up for the same two-day, one-night trip—but we share nods and murmurs of agreement, looking around the rest of the group and acknowledging that, for one reason or another, everyone here wants the outdoor escape that Kimberly described.

We start down a snowy runway with an open view of the Bigelow Range ahead—a beautifully looming backdrop as we weave in and out of the forest—and Sugarloaf Mountain just across the way. The snow is fluffy, thanks to a recent snowstorm; the air is brisk yet comfortable beneath the sun. It’s just warm enough to work up a light sweat.

Snowshoeing can be one of the easiest, most peaceful ways to explore winter. At times, we are so far into the forest that only a sliver of sun shines through the trees. Then we emerge into long open stretches hugged on both sides by trees lined up like dominos so far that it’s impossible to tell if the trail ever ends.

Maine Huts & Trails’s four eco-lodges offer cozy and welcoming way points for skiers and snowshoers trekking through its 80-mile-plus network of backcountry trails.
Photo Credit : Jamie Walter/courtesy Maine Huts & Trails

We each snowshoe at our own pace. I trek along to the rhythm of my breathing, the snow beneath me crunching in sync with the thin veil of icy air I exhale, my only distraction an errant wild creature occasionally dodging across the trail. Distant voices serve as a reminder that a comrade is never far away. 

We travel just over four miles each day (about half a day, with stops along the way), up and down trails that are both steep and gentle, along a route designed to be doable by a varied group such as ours: young and old, novice and veteran.

A new friend is Kay Nash from Orono, Maine, whose adventures have ranged from hiking and rafting the Grand Canyon to biking in Cuba. Soon she will move to the West Coast, so she signed up for this trip as a good-bye to New England. “I looked at doing this for years, and it just never materialized,” she says. “I think sometimes you just have to make the reservation to go—otherwise, things will always get in the way.”

In our group we have an avid hiker looking for fresh territory, a couple from New York in search of “good snow” (something central Maine rarely fails to deliver), and a Maine Huts & Trails enthusiast on her third guided trip. Having climbed many mountains across New York and New England, Ben and Mary Pratt of Biddeford Pool, Maine, were there for a new experience, and something else, too. “Having someone else cook dinner,” Mary says, laughing. Her sentiment is likely felt by everyone at dinner, as heaping plates of roasted chicken, broccoli, wild rice, multigrain bread, cabbage slaw, and carrot cake are set before us. 

Our leader, Kimberly, who keeps a close eye on her snowshoe-clad ducklings on the trail, is a Registered Maine Guide who has worked with Maine Huts & Trails for four years while living in rural Maine (“It’s closer to get my groceries in Canada”). She tells us a story about why the backcountry tours she leads are so important:

“This summer I took a father and his two sons on a trip to the Flagstaff Hut. We went out to an island and camped for the evening; we cooked everything over a fire. He was from the North Shore of Massachusetts, and he said, ‘You know, I’m from a place with 60,000 people, and nobody knows about this.’ It was just so good for him to take his sons out without having to buy all kinds of gear, because it wasn’t something they could do regularly. The boys loved it.”

Among the payoffs for those snowshoeing into this western Maine landscape: views of the Bigelow Range, whose peaks seem even grander in contrast to the frozen expanse of Flagstaff Lake.
Photo Credit : Jamie Walter/courtesy Maine Huts & Trails

Our destination is the Stratton Brook Hut, one of four huts scattered along 80 miles of trails that will eventually encompass 12 huts and span almost 200 miles, from the Mahoosuc Range to Moosehead Lake, similar to European hut-to-hut systems (or, closer to home, the Appalachian Mountain Club huts in New Hampshire’s White Mountains). The network intricately combines wide-open, flat trails with Nordic ski tracks and steep side trails up into the mountains.

Inside our home for the weekend—with its wood paneling throughout, vaulted ceilings, radiant floor heating, and floor-to-ceiling windows—I feel I am in a backcountry hut but one with all the comfort and conveniences of home. We have a drying room for wet clothes, large shared bathrooms with showers, and plenty of warm beverages.

I came on this guided trip alone. But between conversations by the fieldstone fireplace, laughter from card games at the long wooden tables, and freshly prepared meals eaten family-style, I feel connected to all the people who have trekked through the snow to this secluded hut for the night.

Hours earlier, I admit, I had reservations about spending two days snowshoeing with a group of strangers (and, let’s be honest, sleeping in a bunk next to them), but we grew closer, and told our stories, all the while discovering winter in the Maine woods. It was just as Kimberly said: an escape from the chaos of daily life. —Cathryn McCann

‘It’s All About the Dogs’ Peace Pups Dogsledding in Lake Elmore, VT

Ken Haggett
Dogsledding Guide
Winter adventure he’d most like to try: “The [Maine Huts & Trails] hut-to-hut trail network looks like a beautiful place to explore. And the snow conditions would help me decide whether to go by fat bike or by skis!”
Peace Pups Dogsledding, Lake Elmore, VT
Photo Credit : John S. Dykes

Arutted dirt road ends at a parking area in Lake Elmore, Vermont, where a small “Peace Pups” banner confirms that I’m in the right place—prompting a sigh of relief from both me and my rental car, which clearly would have preferred a more suburban landscape. I’d been duly warned that this tour location was a bit off the beaten path, and it is indeed as advertised.

There is no cellphone service. Instead, a sign directs me to a two-way radio that can summon my host if I’m not up for the five-minute walk to the tent site where tours begin and end with hot cocoa and a chill-erasing fire. But the sun is shining and the day is unseasonably pleasant, so I set off down the path.

I hear occasional barks and yips, which get louder as I walk, and before long my host and his team come into view. The eight sled dogs I’ll be riding with, all Siberian huskies, are already in harness and clearly eager for the run. A second team rests in Ken Haggett’s handmade double-decker, truck-borne kennel, having made their dogsled run before my arrival. On the side of the truck, names are hand-painted: Tundra, Zena, Pacem, Ramble, Jazz, Peggy, about 20 altogether.

Ken is the reason I’m here, though he’s quick to point out that “nobody comes all the way out here to see me. It’s all about the dogs.”

As he finalizes the harnessing of the dogs to the gang line at the front of his toboggan sled (also handmade), I favor the team with some head scratches, stoking my Jack London–inspired sled dog fantasies of years gone by.

Before we depart, Ken gives me a quick rundown of the controls. He’ll be at the helm, and my role on this guided adventure will mostly be as human cargo, but it’s still good to know what’s going on. I learn about the snow hook (the dogsled version of a parking brake) and the difference between gang lines, tug lines, neck lines, and snub lines.

Before long, we are off and running: me sitting in comfort, Ken standing at the controls, and the dogs pulling and running from the moment they feel the snub line release.

Our course takes us along a groomed trail from the field where we started, with its beautiful views of the Worcester Range, and into the woods. We pass an old farm site, an abandoned road. There are streams to cross and hills to climb. The dogs set the pace throughout, running when so inclined, slowing to a walk at times.

A Peace Pups team in action. They also run in autumn, when owner Ken Haggett offers rides on the wheeled sleds he uses to get the dogs in shape for winter.
Photo Credit : Mark Fleming

Ken is standing behind me, which makes for easy conversation as we ride. He points out landmarks and shares dog stories. Ken grew up on a dairy farm not far from here. He was a woodworker, but after 30 years he needed a change. Around that time, he and his wife attended a dogsledding event that featured skijoring, in which one or more dogs pull a person on skis. Ken thought it looked like great fun, but his dog at the time, a German shepherd mix named Maura, did not share his excitement. Eventually they agreed to disagree about skijoring, and Maura retired to a life of chasing Frisbees.

But for Ken and his wife, a seed had been planted. They adopted their first Siberian husky, Jake, from a shelter in 2001. More dogs soon followed. By 2005, Ken was flirting with the idea of a dogsled tour business. In 2006, he stepped out of the woodshop for good.

Ken’s current lineup includes 23 dogs, 19 of whom still run. Ralphy and Solar, both age 7, are lead dogs. Fleche, who was adopted from Quebec (his name means “arrow” in French), is the oldest active dog, at 13. 

As we talk, Ken interjects voice commands, directing the team “gee” (right) or “haw” (left). Our course takes us over three loops between woods and fields, a 4½-mile run.

Although competitive dogsledders prefer the more businesslike Alaskan huskies, Ken is dedicated to his Siberians. “I love their personalities, their enthusiasm, their stubbornness,” he says. “I like sharing these dogs with our guests. They aren’t working dogs in the conventional sense. They live like pets.”

I ask Ken how long it takes to train a dog to run with the team, and he laughs. “About five minutes. They have a natural instinct for it. They love to run.” —Joe Bills

A Ticket to the Top Climbing Mount Washington in Winter

Steve Nichipor
Climbing Guide
Winter adventure he’d most like to try: “Snow kiting. It sounds like a great way to get the thrill of speed you get with downhill, but on mellower terrain—like on lakes, which we have a lot of in the Northeast.”
Omni Mount Washington Resort, Bretton Woods, NH
Photo Credit : John S. Dykes

When I lose my ice ax, the realization hits me: This will probably hurt.

It’s early afternoon, and I’ve just started my descent of Mount Washington—moving in a slow, deliberate diagonal pattern across a sheet of thickly crusted snow—when one of my crampons catches, and I fall. There, atop that shimmering, slick surface, I begin to slide on my stomach. Faster and faster. When the ax slips out of my hands, so too does the only surefire way I know to stop. For the next 100 yards, I slide down the peak like some surprised participant in an obscure Guinness World Records event. And still I keep thinking, Surely I’ll slow down. Something will stop me.

I am right, sort of.

Ahead waits a set of boulders. The one I hit is shaped like a ramp, sending me flying. Then I land on my back with a thud. After a few long moments—Are all my limbs still attached?—I blink the world back into existence. In the distance, I hear, “Are you all right?”

I slowly sit up to see my guide, Steve Nichipor, moving quickly toward me. “I think so!” I yell, groggy but embarrassed that I’d forgotten his instructions on how to dig in with my ice ax. My overstuffed backpack had managed to absorb most of the blow. Aside from a sore right elbow, I seemed to be intact. Steve does a run of diagnostics, then offers water. He keeps his eyes on me as I eat an energy bar.

While I had scaled Mount Washington in a variety of ways during summer—train, car, and on foot—a winter climb was something I’d anxiously sidestepped. I wanted to do it, and I didn’t want to do it. This is not a mountain for the novice, or the careless, at any time of year, but in snow and ice it’s especially treacherous.

In Steve Nichipor I found my ticket to the top of Northeast’s tallest peak. Over the past quarter-century, the Connecticut native has worked and climbed the Whites in every season and in all kinds of weather conditions. His résumé reads like that of a Ph.D. in Washingtonology. He’s guided independently for the Appalachian Mountain Club and Eastern Mountain Sports, and for the past decade he’s worked as an outdoor guide for the Omni Mount Washington Resort. The easygoing 47-year-old has led visitors from across the world and from many different walks of life. There was the pair of 12-year-old ice climbers he introduced to the region, the crew of college guys from Singapore he guided through heavy January rains, and the retired Connecticut man who made an annual pilgrimage out of hiking with Steve each winter. “He’s our go-to guy,” says Craig Clemmer, the hotel’s director of marketing. When Good Morning America wanted to film a segment on a winter climb up Mount Washington, the hotel turned to Steve. 

The most popular winter trek up the mountain begins at the Pinkham Notch Visitor Center in Gorham. Inside the building is a sign detailing how hikers should dress “like an onion” for a winter climb. Layers, in other words. And, as I get started on my own guided winter adventure here, layers I have. Multiples of long underwear, a few different jackets, thick gloves and mittens, socks upon socks. I’ve rented plastic boots and crampons from International Mountain Equipment in North Conway, and I borrow an ice ax, ice spikes, and trekking poles from Steve.

The four-mile climb covers a robust 4,200 feet of elevation along mixed terrain: a relatively easy stretch along the wide Tuckerman’s Ravine Trail; a steep, icy ascent up Lion Head. During the early sections I hear myself saying, “Look at that view of Wildcat!” and then, a few minutes later, “What a view of Wildcat!” And so on. Steve takes it in stride. “It gets better and better,” he says.

Summiting New England’s highest mountain might be the ultimate winter adventure, but it’s not to be undertaken lightly.
Photo Credit : Cait Bourgault

Closer to the top, we peer into Tuckerman’s Ravine, and at the base of the summit cone, we rest. Then it’s time to make a final push to the top. What awaits is as beautiful a winter picture as I’ve ever seen. Under crystal-clear skies, the parking lot and the final stretch of the auto road are blanketed in ice; rime ice and snow covers most of everything else. “I’ve never seen it like this before,” Steve says. Just as astonishing is that Mount Washington’s famous weather isn’t showing its face today. We are in a bicolor world. White below and around us; blue overhead.

Tucked away from the wind, Steve and I scarf down bagels at the top. Then we begin our descent—and yes, for a short stretch at least, I manage to move a little faster than my guide. I was grateful for his guidance up the mountain but even more so going back down, as we gingerly proceed after my fall. At one especially icy stretch, he ropes us together and rappels me over the terrain.

“We’ll just take our time,” he says several times. And so I do, mindful of my sore elbow and ego, and in awe of the fantastical winter landscape we are trekking through. —Ian Aldrich

A Trail Ride Through Snowy Lincoln Woods Sunset Stables in Lincoln, RI

Linda Oliveira
Trail Riding Guide
Winter adventure she’d most like to try: “Dogsledding, because I do love canines. But probably just for a few hours, rather than an overnight trip—I really look forward to my shower and coffee in the morning!”
Sunset Stables, Lincoln, RI
Photo Credit : John S. Dykes

Scoot your butt to the left! Are you doing OK, Kim? We’ll wait for you. Sit up!”

Linda Oliveira barks this back at me from her horse at the head of our trail ride, punctuating the plodding beat of hooves on snow-sugared ground. Her voice is impassioned like a Little League coach’s: correcting, encouraging. But it’s not the loudest one I hear. Even the constant dialogue—OK, monologue—that I’m keeping up with my mount, gentle stable favorite Champ, can’t compete with my late mom’s insistence: You are not riding a horse.

But I am, in flagrant violation of a family policy that originated before I was born, when Mom’s pride and backside were injured in an equine mishap. With less instruction than the Honda salesman provided before I pulled away in my four-wheel-drive, I am steering a 1,200-pound, all-terrain creature with the distractible disposition of a 2-year-old.

Reins left to go left. Reins right to go right. Pull back to stop. Heels to move along. Grip the saddle horn with your other hand. Even as I juggle my Nikon, it seems pretty straightforward. The country music pumping from speakers at Sunset Stables fades, and I can feel every muscle in this bay beauty’s back working as our small group sets out single file. Ahead of me, riding Champ’s best buddy, Shadow, on this cobalt-sky Saturday’s first trail ride, is my theatrical 15-year-old, who is eager to add horseback riding to the skill set that might land her a movie role. I’m envious of the Lara Croft confidence she projects astride her white-stippled red roan (even though Shadow’s attention falters whenever something in the wintry landscape looks remotely like a snack).

On a Sunset Stables winter trail ride, surefooted and laid-back mounts carry their riders down a snow-covered slope in the 627-acre Lincoln Woods State Park, near Pawtucket, Rhode Island.
Photo Credit : Kim Knox Beckius

The temperature drops 10 degrees as we venture at a slow and steady, novice-friendly pace alongside a frozen pond, down weathered banks, and around Lincoln Woods State Park’s massive glacial boulders. It’s an obstacle course planted millennia ago: awe-inspiring and serene. Yet I’m nervously prattling in Champ’s perky ears as we bring up the rear. “Do you see that downed tree, Champ? Do you know how to step over a tree? God, I hope you’ve got this.”

He does. And he lets me know it with an emphatic snort. Linda, our leader, reassures me that he’s just clearing dust particles from his long, strong lungs. She’s been wrangling horses here for more than 40 of the Lincoln, Rhode Island, facility’s nearly 100 years and has co-owned the year-round operation with Jim Borden since the state rescued the property in 2004. They’ve selected saintly, versatile horses that compete, teach, and hit the trail in up to four feet of snow. Bug-free, no-sweat winter treks are best, Jim says. They’re available to walk-ins on winter weekends and by appointment weekdays.

Faced with a steep, snow-slicked hill to ascend, I resist the urge to squeeze my eyes shut. Progress. When I let the braided reins slip from my hand as I’m framing a shot, Champ ramps up his gait, and I’m jolted back to my driving duties. Mom’s admonitions boom. Linda’s, too. Yet I retake control calmly. “Whoa, Champ. Work with me, pal.” I’ve already talked to him more this winter than to most humans I know.

I’m not eager to dismount when the barn and bonfire reappear. I’ve just started to notice bird sounds … to search for signs of fox, deer, and coyote in the leaf-stripped, wide-open woods … to feel soothed by this moving meditation. A peppermint candy and a pat on the neck seem inadequate thanks for my Champ, who earned my trust and changed “you can’t” to “you can” in an hour—and who ensured that my daughter’s sense of adventure won’t be limited by ancestral fears. —Kim Knox Beckius 

More Guided Winter Adventures in New England:

On the Wild Side

Fish Nerds Ice Fishing ToursFamed for his quest to catch (and eat) all 48 fish species in New Hampshire, Clay Groves combines his science-teacher background with piscatorial expertise to lead all-ages ice fishing tours in the White Mountains. Conway, NH

RiverQuest Eagle CruiseBoard the River­Quest for a two-hour cruise on the Connecticut River, and you’ll have the chance to spy all manner of winter wildlife: majestic eagles, yes, but also swans, seals, coyotes, deer, and more. Haddam, CT

Birding with Mass AudubonMassachusetts’s largest nature conservation nonprofit offers birding trips for all ages, from “owl prowls” to coastal watches. One highlight: a two-day jaunt from Newburyport’s Joppa Flats Education Center in January. Locations statewide

Hit the Heights

Bretton Woods Canopy TourZip-lining isn’t just for summer. At the Bretton Woods ski resort, riders can buckle in for a three-hour winter thrill ride that delivers spectacular views of the western White Mountains. Carroll, NH

SnowCoach ToursIf you can’t climb Mount Washington, get a ride: A van mounted on tank tracks, the SnowCoach takes visitors on a round trip to the tree line; avid snowshoers have the option to hoof it back down. Gorham, NH

Ice Climbing at IMCSCheck out this adrenaline-goosing sport at the International Mountain Climbing School, whose home base in the Whites gives easy access to some of the best climbing spots in the East. Group and private guided tours available. North Conway, NH

Go Full Throttle

New England Outdoor CenterThis venerable Maine outfitter offers three-hour weekend guided rides that newbies will love: Before hitting well-groomed trails that deliver prime Katahdin views, they can rent any gear they lack, from bibs to boots. Millinocket, ME

Green Mountain Snowmobile AdventuresAfter a day skiing down Smuggler’s Notch, why not turn around and snowmobile back up? Take an evening tour into the Notch Pass for winter views that few others get to see. Jeffersonville, VT

Northern ExtremesWith tours ranging from an hour to overnight, and covering both the Whites and the Great North Woods, this outfitter makes the most of the longest snowmobile season in the state. Carroll and Bartlett, NH

Blaze a Trail

Dogsled CampingYes, the pros at Mahoosuc Guide Service can take you deep into the Maine woods on dogsledding overnights that go from a few days to nearly a week. For epic wilderness immersion, though, check out their nine-day trek in Nunavik, the arctic region of Quebec. Newry, ME

Backcountry SkiingThe Catamount Trail Association leads one-day tours that are open to all, but a CTA membership will get you in on multiday trips that explore different sections of the trail, which runs from the Massachusetts border clear to Canada. Burlington, VT

For more ways to have some wintertime fun in New England with the whole family, check out our Family Guide to Winter Fun in New England.