The Mt. Peg: A Gateway to 30+ Miles of hiking trails
ACTIVITY ON THE RIDGE
At Skyland, you don’t just have trail access; you have the best seat in the house for the Mount Peg trail network. With 16 miles of beautifully managed trails right at your doorstep, the property serves as a natural anchor for a vast, 30-mile interconnected web of forest paths stretching toward the Vail Forest and Mount Tom.
This is a landscape designed for exploration at any speed—whether you’re looking for a peaceful 45-minute stroll to clear your head or a long afternoon adventure through the woods, all without ever seeing a paved road.
Managed through a dedicated partnership with local trail organizations, these paths represent the heart of Vermont’s outdoor culture: expertly maintained for summer hikes and professionally groomed for quiet winter snowshoeing and cross-country skiing. It is a world-class playground, kept in pristine condition for you to enjoy in every season.
THE SUMMIT START: GRAVITY-FED FLOW
For the mountain biker, Skyland eliminates the need for a "climb to the trailhead." From your own backyard, you are already at the high point of the network, allowing you to drop directly into the flow of the mountain. Whether you’re looking for the natural granite tech of the North Ridge or the smooth, manicured berms of the lower loops, the terrain is your personal playground.
This is the heart of Vermont’s celebrated trail culture. Through a dedicated partnership with WMTB, the trails are constantly evolving to offer the best of modern riding—from scenic, winding climbs to long, rewarding descents. At Skyland, there’s no need to load a rack or check a GPS; you simply open the gate, clip in, and enjoy the ride.
Recovery
Beyond the pace of the chase, the ridge offers the ultimate environment for active recovery. Whether it’s a high-altitude hike to clear the mind or a sunrise walk with the dogs, the immediate trail access ensures that even your 'off' days are spent at the summit.
The Gateway to a groomed nordic empire
Winter: Your Private Nordic Sanctuary
At Skyland, winter is a season to be embraced, not just observed. The same ridgelines that define your summer walks transform into a beautifully groomed Nordic circuit the moment the snow falls. Step out of the mudroom and directly into your stride—whether you enjoy a peaceful morning cross-country ski or a rhythmic snowshoe through the deep woods, the transition is seamless.
This is the ultimate backyard winter retreat. Maintained to the high standards of the Woodstock Nordic Center, the trails are kept in pristine condition for a smooth, consistent glide. Here, there’s no need to wait for the plows or drive to a crowded lodge. You simply clip in, find your pace, and enjoy the quiet beauty of a Vermont winter.
WINTER RECOVERY: THE SILENT RIDGE
For the moments between high-output sessions, the ridge offers a sanctuary for active recovery. Beyond the groomed track, the terrain invites the deliberate pace of snowshoeing and backcountry exploration. It’s a landscape designed for mental recalibration—whether breaking trail through fresh powder or navigating the hushed pine corridors on touring skis.
At Skyland, you don’t just observe the winter from a window; you inhabit it. It is the ultimate luxury of space: the ability to choose between the intensity of the track and the solitude of the forest, all within the boundaries of your own backyard.
Ice, snow, and legacy
The Softer Side of Winter
Winter at Skyland is a private event. The estate pond is engineered for more than just aesthetics; it is an arena for hockey and skating, offering a pristine, home-based sheet of ice. Beyond the pond, the rolling grade of the farm provides dedicated runs for sledding and tubing that rival a private club. These aren’t just seasonal features; they are the infrastructure for a life lived outdoors. Here, winter isn’t a season to endure—it’s a season to explore.
SASKADENA SIX: THE 6-MINUTE MORNING SESSION
KILLINGTON & PICO: THE BEAST AT YOUR BACK DOOR
KILLINGTON & PICO: THE BEAST AT YOUR BACK DOOR
At Skyland, the transition from breakfast to the chairlift happens in minutes. Saskadena Six isn't just a mountain; it’s a storied extension of your backyard. Known for its intimate, soul-of-skiing atmosphere, it is the premier environment for the next generation to find their edges. While the technical terrain of 'The Face' provides plenty of challenge for seasoned skiers, the gentle, sun-soaked glades offer a safe, low-stress sanctuary for family afternoons. This is Vermont skiing as it was meant to be: no crowds, no chaos—just a historic, community-focused hill where the lift operators know your name and the memories are built on every lap. It’s the ultimate luxury of convenience for the active family.
KILLINGTON & PICO: THE BEAST AT YOUR BACK DOOR
KILLINGTON & PICO: THE BEAST AT YOUR BACK DOOR
KILLINGTON & PICO: THE BEAST AT YOUR BACK DOOR
For the days that require 3,000 feet of vertical and 1,500 acres of terrain, the 'Beast of the East' is a straight shot down the valley. Killington and Pico provide the ultimate big-mountain training ground, featuring world-class steeps, legendary moguls, and the longest season in the region. At Skyland Farm, you are close enough to catch the first chair on a powder day, yet far enough to retreat to the silence of your own ridge before the après crowds arrive.