Winter Park Way

Winter Park WayThe WINTER PARK WAY has been in the making over the last four years but with the 2019 season now finished, I think we have a plan. AND, it’s good.  Winter Park is a world renowned ski area in the central mountains of Colorado and just over the Continental Divide.  Once past the ski area the Fraser Valley sweeps north. Cattle graze on the high plain with foothills then higher mountains to the east and west.  What makes it different from the WTW?   First and foremost- lodging is more modern- no rustic lodging with bathrooms down the hall.  Lodging areas includes: Winter Park Resort, Winter Park Town and Devils Thumb Ranch. 

Second- the hiking is different. The first two days are door to door beginning on the 6,000 acre Devils Thumb Ranch.  These days are undulating and will ease you into the rarified air.  The route ends with a spectacular day on the tundra and a chance to hike all the way back to the ski area where you catch the gondola down.  Very fun!!

We hope to have prices and dates updated by December 1st.  Trips offered for next year are 4nights/3days and 3nights/2days


All trips include:

  • Lodging 
  • Breakfast
  • Good packed lunches
  • Route guide and maps
  • Shuttling within route
  • Trekking poles for trip

Not included:

  • Evening meals
  • Personal Items
  • Transportation to and from Winter Park

How to get there:

From DIA – Denver International Airport:

  • Arrive Winter Park by shuttle–Home James Shuttle can be booked at
  • Arrive by car- Park at Devils Thumb Ranch or Vintage depending on where your trip ends


Booking information

  • Email preferred length of trip (there are three offerings), dates, number of people, number of rooms and number of beds per room.  
  • A $300 deposit per room is due once the trip is booked and confirmed
  • Balance is due 60 days prior to your trip date.
  • Once paid, you’ll receive a full packet with your route guide, maps, gear guide, park information etc.
  • Upon arrival you’ll receive another packet with your luggage tags and car voucher


  • Arrival day: We will contact you about a week prior to your trip to confirm your arrival plans.  You’ll meet your trip manager in the early evening to answer any questions and make sure you’re ready for the following hiking day.
  • Hiking days: As with the Walter Tishma Way, we have found the use of a morning shuttle to be a good thing.  Gives you a chance to see your trip manager to keep your trip running smoothly.  There are two days on the WPW that are door to door.  You’ll still see your manager in the morning.
  • Last day of hiking: Your last hiking day will take you to your last lodge.  After breakfast the following morning you’re done!
  • Be sure to make your flight reservation to allow for enough time for your transfer back to DIA if booking the shuttle. 
  • There is a luggage limitation of one piece of carry-on luggage per person for transfer.  If you have more it can be stored with us and we’ll return it to you at the last lodge.  We will realize most airlines limit luggage so a good idea is a packable duffle that can be used during the week.  If you have any concerns or needs please contact us.

Inn-to-inn hiking is not just about the hiking, the lodging should be fun, diverse and representative of the area. It’s like a smorgasbord with each place offering something different.

Devil’s Thumb Ranch What a beautiful place to start.  You may not want to leave.  This exclusive ranch-resort is located on 6,000 acres nestled at the bottom of Devil’s Thumb Pass.  While quite luxurious, the feeling is laid-back and welcoming.  If you’re booking a 5night/4day trip, you will begin and end at the ranch and may want to book a massage after that last day of hiking.  This is also the perfect place to add days at the front or end of your trip.  

Trailhead Inn -Winter Park Town- This recently renovated lodge is also owned by Devil’s Thumb Ranch.  It is centrally located in the town of Winter Park, close to restaurants, bars and shopping.  The lodge is initimate, but not too intimate.  Pool.

The Vintage Hotel in Winter Park Resort- Winter Park Resort is just up the road from the town and is the base area for the world-renowned Winter Park Ski Resort.  The Vintage Hotel is about a 10 minute walk from the village or if running, you can take the Cabriolet lift right to the front door.  This is an older hotel, but has spacious rooms and is extremely comfortable.  Pool and huge hot-tub.  Five night and four night trips will spend two nights here.


Elk Meadows Day
Elk Meadows to Winter Park Resort
Distance- 9 miles
This is an excellent first day for a 5night/4day trip.  The terrain is undulating with no sustained up and stays around 9,000 ft.  This will give you a chance to acclimatize and get your legs going.  Route uses several mid-level bike/hike trails.  There are intermittant views and a good finish right into Winter Park Resort where you can stop off for an ice-cream or go have a beer.  Finish out at the Vintage Hotel with a relaxing time in the pool or hot-tub.
Broome Hut Day
Second Creek to Winter Park
Distance- 7.5 miles. 5.5 if you catch the lift down
Difficulty- High Moderate
High Point- 11,500 ft.
Beginning- 10,585 ft.
This is a pretty cool day with top of the world views  Broome Hut is part of the 10th Mountaineering Hut System and is a fun place to visit.  Day begins high with a short shuttle to Second Creek Trailhead at 10, 585 ft.  Once past hut the trail climbs up near the Continental Divide and makes its way down to the new Gondola at Winter Park Ski Area for a quick trip back down to the resort.
Divide Day
10+ miles
More Difficult
10,000 ft. start
12,000 ft. high
1,500 vertical gain
The Divide is offered on the 5night/4day trip and is the queen stage of the WPW.  The route is circular with several options for length but does require some experience in “reading the terrain” for some off-trail climbing.  Hikers should be able to hike 10+ miles.  The van will get you pretty high to start out and your trip manager will be in the vicintity all day as all hikers will return to the van for return trip.  We’ve worked a lot on this day to give as much bang for buck as possible.  It’s a winner!
Red Gate Day
Winter Park Town to Devil’s Thumb Ranch
Devils Thumb Ranch to Winter Park
8.5 miles
9,000 ft.
This is a lovely day mostly on Devils Thumb Ranch property.  Lots of meadows, aspen trees and cows- a good way to start or finish.  This is the first day for 3night/2day trips and 4night/3day trips.  It’s the last day for the 5night/4day trip.  The day is door to door.

To book the Winter Park Way contact us with your preferred dates and let us see if we can accommodate you. Let us know the number of people and whether they are double or single occupancy.

If booking a double occupancy room let us know whether you prefer a room with one or two beds. 

If you have any other questions concerning the trip, just use the “Submit a Question” button at the top of the page.