Windham

Just over two hours from New York City, Windham presents itself as a convenient weekend getaway during the cold winter months. There’s no mistaking this mountain for a true destination, but a couple of factors help it stand out against other local competitors.

With a 285-acre footprint and 1,600-foot vertical drop, nobody is going to be mistaking Windham for a massive mountain. But it’s not exactly a small hill either, and although trails generally feel similar to one another, the resort offers a fair range of terrain for various ability levels, from first-timers to more experienced guests. The resort is family-friendly, and while there are a few distinct mountain pods—and some catwalking is involved to get to some of the farthest out trails—the singular base area makes it difficult to get lost.

While only about a fifth of Windham’s terrain is rated as green, the resort is a solid choice for less experienced skiers and riders. The Whiteway chair, which has newly been upgraded to a high-speed quad, is dedicated to beginner terrain, while the Wonderama and East Peak lifts both service one green run each. While the main resort summit doesn’t offer any green runs, the Upper Wraparound blue trail could easily be mistaken for a green at many larger East Coast mountains; the same is true for most of the blues off the Wonderama chair.

Windham offers a range of groomed, blue cruisers for intermediate guests. Nearly every blue-rated trail is congregated off the Westside Six chair—and they all feel pretty interchangeable—but the resort also features slightly steeper blue-black trails in other mountain areas that are more distinctive. But ultimately, intermediate guests will likely find themselves lapping the Westside pod, and visitors of this proficiency may start to get bored after a day or so at the resort.

Guests will really start to grow out of Windham’s terrain once at advanced proficiency. It would be a stretch to say that single-black runs feature anything more than a typical intermediate pitch—most of them would likely be marked as blues at any major Vermont resort. The resort’s double-blacks do have some respectable steep pitches, but they’re quite short. These pitches tend to be really icy, and at most times, the most challenging aspect of the mountain is digging in your edges here so you don’t wipe out. If you’re looking to get your leg day in, you won’t find it at Windham; black and double-black runs are regularly groomed, and mogul runs are rare.

Windham’s lift network is a standout. Now that the Whiteway triple has been replaced with a detachable quad, every section of the mountain—save the bunny hills—is directly served by a high-speed lift.

Windham’s lift infrastructure also helps mitigate crowds. As one of the closest ski resorts to New York City, Windham is no stranger to long lines on weekends and holidays. But the three high-speed lifts from the base, each of which generally caters to different abilities, help spread out crowds and keep things moving quickly enough. This is in stark contrast to some competitors that have unbearable lines nearly every weekend of the season. However, most of Windham’s lifts are either at or close to the base—and if you’re there on a weekend, it’s really hard to avoid waiting in at least some flavor of line after every run. On the busiest days, the Baker double provides a redundancy from mid-mountain to the summit; this lift is slow, but lapping it is often the best way to get away from the crowds.

Windham receives unexceptional natural snowfall throughout the winter and relies heavily on snowmaking to operate. That being said, Windham’s snowmaking capabilities have improved quite a bit in recent years, and the resort now has some of the best operations in the Catskills. The resort is usually able to get every mountain zone open by the core season—typically with some flavor of every terrain difficulty—and employs extensive grooming to maintain quality slopes. 

However, Windham is not immune to the variable natural weather conditions of its southeastern New York location, and freeze-thaw cycles are regular occurrences. Even rain spells aren’t out of the question during the core season. Windham can take awhile to recover its slopes in the event of these unfortunate weather conditions, so booking an in-advance trip—especially in December, early January, or March—can be a somewhat risky proposition.

If you’re looking to escape from the weather, Windham does have some practical lodges to stop in for a break. These include a main base lodge, which features both a more casual cafeteria and a fancier restaurant, as well as the mid-mountain Wheelhouse Lodge, which allows guests to stop in without going all the way to the base. In addition, several food trucks provide food service at the base.

Getting There

Perhaps the most attractive part about Windham is how close it is to New York. The mountain is approximately two and a half hours from the New York City metropolitan area, and even closer from some New Jersey and Westchester suburbs.

Bus services exist between the town of Windham and New York’s Port Authority bus terminal, typically leaving New York daily around 8:30am and departing Windham around 4pm. Additionally, several private NYC-area ski clubs run day or weekend trips to the resort; these can be a great way to get to the slopes if you don’t have a car.

Lodging

While many Windham visitors will only be driving up for the day, several lodging options exist both on site and close to the resort. The resort offers a variety of ski-in/ski-out accommodations near the base, including some very fancy condos, but these are quite pricey. Cheaper inns and motels can be found within a short drive of the mountain.

Aprés-ski

As a day trip mountain, Windham is fairly sleepy once the sun goes down. That being said, there are a handful of bars and restaurants to explore after a day on the slopes.

Verdict

Windham can’t boast the natural snowfall, acreage, or terrain diversity to beat out the true East Coast destinations. But it also lacks some of the major issues, such as amusement-park-level crowds and over-commercialization, that plague some nearby competitors. That said, lift ticket prices have risen over the years, and if you purchase your tickets close to the date of your vacation, you’ll be paying the same as—or more than—the best destination Vermont resorts. For the 2022-23 season, prices are now as high as $175 for a 1-day adult ticket on peak days; choosing to pay this rate means tossing any reasonable financial judgment in planning a ski trip.

If you’re planning a full-week trip, you’ve ever made it past a beginner slope, or tickets for your vacation date are already over $100, Windham doesn’t make much sense. But if you’re looking for a NYC-area day trip destination to kill a couple of hours—and you either have an Ikon Pass or plan well in advance—Windham isn’t a bad way to go.