Windham Mountain

  • Image - Windham Mountain
  • Image - Windham Mountain

Windham Resort

Windham 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

NYC’s Mac & Cheese Truck

NYC’s Mac and Cheese truck is on the back patio! Get delicious mac and cheese after a morning on the slopes.

East Coast Street Tacos

Visit the back patio to get yourself a taco from the East Coast Street Tacos food truck!

Umbrella Bar

It’s always après at our European-inspired patio bar featuring craft beers on tap and quick bites in enclosed, heated comfort.

Cave Mountain Cafe Bar

A much anticipated addition to Windham’s food service in the lower lodge. Just follow the aroma of the freshly roasted beans, and you’ll be in coffee and cappuccino heaven and on the go pastries, wraps, soups, and more.


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.

Seasons 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 cafe lattes and cappuccinos.

Cave Mountain Cafe Bar

A much anticipated addition to Windham’s food service in the lower lodge. Just follow the aroma of the freshly roasted beans, and you’ll be in coffee and cappuccino heaven and on the go pastries, wraps, soups, and more.



COVID-19 Safety

Urban Sherpa Travel is committed to the health and safety of our guests and our team. Please be aware that exposure to COVID-19 is an inherent risk in any public location where people are present. We have taken numerous steps to reduce this inherent risk and ask that you familiarize yourself with our COVID-19 health and safety requirements and precautions prior to your visit. You should evaluate your own level of risk when determining whether to visit. By traveling with Urban Sherpa Travel you acknowledge and agree that you assume these inherent risks associated with your attendance as we have explained them to you. Please see our complete COVID-19 Safety Statement.


Due to restrictions at Windham Mountain we will be offering limited lift passes and more often transportation, please book early to take advantage of our lift pass sales.  If you are planning to join our bus trips and are not able to purchase a lift pass from Urban Sherpa Travel, you can purchase a lift pass from the Windham Mountain website.  You must also purchase rentals and lessons from Windham’s website.

Basic Package for advanced beginners and up includes a round-trip bus pass and lift ticket, Not Available.
Round-Trip Coach Transport Only includes a round-trip bus pass.  $69.
One-Way Coach Transport Only includes a one-way bus pass.  $59.

Custom Options

Lesson Add a 90-minute group lesson to improve your ride (beginner, advanced beginner, or intermediate levels available) Please be aware that the 9:30am time slot will be reserved for beginners and first timers (green trails) only and the 1:30pm time slot will be for intermediate and advanced (blue and black trails) only. Must be purchased from the Windham Mountain website.
Gear Rental Ski rental includes helmet, shaped skis, poles, and boots; snowboard rental includes helmet, board, boots, and bindings must be purchased through the Windham Mountain website.
Outerwear leasing can be arranged through Windham Mountain Outfitters

Logistics | Pickups & Departures

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

Pickup/Dropoff Locations

  Union Square 6:00am Times Square 6:20am
Depart 6:15 AM 6:30 AM
Depart Windham Mountain 4:15 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

This trip is currently not available