Windham Mountain

  • Image - Windham Mountain
  • Image - Windham Mountain

Windham Resort Earns New Yorkers’ Mountain of Choice Award

Windham has become our most popular mountain and is just two hours-and-a-half from our Urban Sherpa pick-up locations in the city. If you haven’t been to Windham, sign up and experience Windham’s expansive runs. The consensus with all our leaders: Windham has more to offer for every skier and boarder.

Just starting out? Wooly Bear is the perfect slope for practicing your stops and turns. Getting better? Take Wide Connection to Upper Wipeout then turn down Lower Wipeout for a mile’s worth of practice. Intermediates looking for an adrenaline rush can check out Lower Wolverine or Upper Wiseacres. Experts out for a sick run should definitely hit Upper Wheelchair or head out to the east peak. Skiers and boarders who like to catch air will want to check out the Big Bag, a huge inflatable for invert practice.

Terrain Parks


The Jib Park

A good way to keep things interesting is to visit the Jib Park. It’s full of rails, hits, and features that change on a regular basis. It’s also lit for you night owls.

The Warm Up Park

Located on the Warm Up trail, this park has the biggest hits on the mountain. It’s sure to challenge even the best skiers and riders.

Lower Wraparound Park

This is a beginner park with small rails, jumps and rollers. Perfect for working on your skills before tackling the bigger stuff.

Lower Warpath Park

Currently set up with medium-sized jumps and skiercross/boardercross banked turns.


The restaurants of Windham Mountain offer a variety of fine and casual food and a range of dining atmospheres.

Windham Mountain - bar scene

Wunderbar Cafe

Windham’s newest dining spot, located on the first floor of the lodge, is perfect for grabbing something on the go—coffee, pastries, wraps, soups, and more.

The Waffle Hut

Need something hot and delicious right before ya jump on the first chair? Located outside by the D-Lift, the Waffle Hut lets you grab a sweet treat and not lose a step. It’s awesome and having your gear on makes it that much better.

Mountain Express Cafeteria

If you’re near the base area, stop into the newly expanded Mountain Express Cafeteria for a quick bite to eat. It’s a casual atmosphere with tasty cafeteria-style selections. Be sure to try the new deli sandwich and soup bar.

Legends Bar & Grill

This après-snow hot spot serves a variety of beverages, bar food, and a great lunchtime menu. Try the mountain salsa and warm chips while you’re there. They also serve Starbucks™ cafe lattes and cappuccinos.


A much anticipated addition to Windham’s food service, at two locations in the lodge. Just follow the aroma of the freshly roasted beans, and you’ll be in coffee and cappuccino heaven.

Mr. Lee’s Sushi Bar

Grab yourself a seafood roll, sashimi, or any of Mr. Lee’s other specialties. Located in the second-floor cafeteria.


Basic Package includes a round-trip bus pass and lift ticket Sat,Sun $95 / Mid Week $85.
Full Beginner Package includes a round-trip bus pass, a lower mountain lift ticket, 90-minute group lesson, a helmet and a board or ski rental $140.
Round-Trip Coach Transport Only includes a round-trip bus pass. You may also add lift ticket, lesson, or gear rental options Sat,Sun $55 / Mid Week $49.
One-Way Coach Transport Only includes a one-way bus pass. You may also add lift ticket, lesson, or gear rental options Sat, Sun $45 / Mid Week $39.

Custom Options

Lift Ticket Just need a lift ticket? Buy it here and pick it up on hill from your Urban Sherpa Leader Sat, Sun $60 / Mid Week $45.
Lesson Add a 90-minute group lesson to improve your ride (beginner, advanced beginner, or intermediate levels available) $34.
Gear Rental Ski rental includes: helmet, shaped skis, poles, and boots; snowboard rental includes: helmet board, boots, and bindings $40.
Outerwear leasing can be arranged through Mountain Threads

Logistics | Pickups & Departures

  • Please arrive 15 minutes early.
  • Bring water, a morning snack, and warm, waterproof, weather-appropriate clothing.
  • Outerwear leasing can be arranged through Mountain Threads.

Pickup/Dropoff Locations

  Union Square Times Square
Depart 6:15 AM 6:30 AM
Depart Windham Mountain 4:30 PM
Return 7:30 PM 7:15 PM

Permissions Slip for Minors

A parent or legal guardian must complete and bring along a Minor Permissions Slip for each child age sixteen (16) and under.

How do I select the correct snowboard stance?

Your bindings settings usually follow your batting stance. If you are right-handed and bat right-handed, then you will probably feel most comfortable with your left foot forward (regular). If you are left-handed or bat “lefty,” then you will likely feel right foot forward is more natural (goofy).

These are just guidelines to start. We can help you find the right fit for your ride.

What type of skier are you?

Image - Ski Ability

Determining your ski ability is your responsibility!

Your ski ability, height, weight, age, and boot-sole length are used by the shop to determine the visual indicator settings of your ski bindings. Be sure to provide accurate information, as any error may increase your risk of injury. Consult the skier type descriptions to select your classification. These descriptions are compatible with ASTM and ISO documents.

Type I Skier (Beginner)

Cautious skiing at lower visual indicator settings

  • Prefer slow to moderate speeds
  • Prefer gentle to moderate terrain
  • Receive lower-than-average visual indicator settings (this may increase the risk of inadvertent binding release in order to increase the likelihood of release in a fall)
  • Type I settings apply to entry-level skiers uncertain of their classification
  • Type I- setting apply for skiers who desire visual indicator settings lower than settings for a Type I skier

Type II Skier (Intermediate)

Moderate skiing at average visual indicator settings

  • Prefer a variety of speeds
  • Prefer varied terrain
  • Type II settings apply to skiers who do not meet all the descriptions of Type I or Type III classifications

Type III Skier (Advanced)

Aggressive skiing at higher visual indicator settings

  • Prefer fast speeds
  • Prefer steep terrain
  • Receive higher-than-average visual indicator settings (this may reduce the likelihood of release in a fall in order to reduce the risk of inadvertent binding release)
  • Type III+ settings apply for skiers who desire visual indicator settings higher than settings for a Type III skier