{ Trips } Skiing & Boarding

NYC + BOS

Big Sky

Big Sky features the best in-bound terrain in North America. Regardless of your level of ability this mountain has more trails, more lifts, more bowls and more glades than anywhere else. The Tram continues to transport technical skiers and riders to some of the most difficult terrain in the country.

This trip is not currently available.

NYC

Hunter Mountain

Hunter is our home away from home and our Urban Sherpa riders’ most popular hill. The terrain at Hunter includes vertical, parks, moguls, and run-outs for experts and gradual lines for beginners.

This trip is not currently available.

NYC

Jay Peak Weekends

Jay’s extensive glade system and incredible snowfall make this a big mountain experience and is a must for those riders looking to knock off challenging terrain. Prepare for an adventure and settle for nothing less.

This trip is not currently available.

BOS

Killington (Boston)

Killington Resort, the largest ski and snowboard resort in eastern North America, is known for long seasons, abundant natural snowfall, and the most extensive snow-making system in the world.

This trip is not currently available.

NYC

Killington (New York)

Killington Resort, the largest ski and snowboard resort in eastern North America, is known for long seasons, abundant natural snowfall, and the most extensive snow-making system in the world.

This trip is not currently available.

BOS

Loon Mountain

Loon Mountain will be one of our go-to mountains. Why Loon? ’Cause it’s an awesome mountain with terrain for everyone, with more snow than ya know. Loon also has a Burton Learn-to-Ride (LTR) program.

This trip is not currently available.

NYC + BOS

Mount Snow

Mount Snow has four mountain faces. That means whoever you are, Snow has got enough terrain diversity to keep a grin on your face all winter.

This trip is not currently available.

NYC + BOS

Steamboat

Head out west to Steamboat Springs, and hang your ten-gallon hat alongside one of the most preferred properties on the mountain. A complete mountain range, with 2,965 acres (1,200 hectares) of permitted terrain offer a diversity of trails for all levels of ability.

This trip is not currently available.

NYC + BOS

Stratton

Stratton has probably the most impressive uphill capacity in the Northeast; you will wait longer for a cup of coffee at Starbucks than for a chair at Stratton. And with over 600 inbound rideable acreage, you will probably never discover the whole mountain in a single day.

This trip is not currently available.

BOS

Waterville Valley

With consistently good conditions and as much or more terrain than any other New Hampshire ski area, Waterville Valley will be our second, close single-day coach trip from Boston.

This trip is not currently available.

NYC

Windham

Windham became our fastest growing trip last year and is just two hours-and-a-half from our Urban Sherpa pick-up locations in the city. Just starting out? If you haven’t been to Windham, sign up and experience Windham’s expansive runs.

This trip is not currently available.