Mark Freeman aged ten on his previous Steamboat and Winter Park road trip, with little brother Ross and Blue Peter TV presenter Katy Hill

They are all standout memories my son Mark had from his previous visit to Winter Park – 23 years ago, when he was ten. 

Drunken Frenchman is one of the Colorado resort’s signature bump runs, the Baseball Glove is the name given to a striking rock formation on a nearby mountain and the whistle is sounded when freight trains pass through the base area or the passenger service arrives from Denver. And they were all of course still there for Mark to enjoy on his latest visit to Winter Park.

We loaded up our Faction skis, one pair of Candides and one of Chapters, in our Chevrolet Malibu and drove from Steamboat Springs to Winter Park on the next leg of our road trip to some of the 38 destinations in the Ikon Pass multi-resort season pass scheme.

The ‘Baseball Glove’ at Winter Park

Our fabulously scenic drive on US Route 40 took us over Rabbit Ears Pass and through the magnificent sheer rock walls of  Byers Canyon, then through the townships of Tabernash and Fraser before reaching Winter Park.

We were on Route 40 for just 100 miles but we were still following an iconic part of America’s history. It might not have the cachet of Route 66, but US 40 is also known as the Main Street of America.  As with most routes whose numbers end in a zero, US 40 once traversed the entire United States. It’s one of the original U.S. Highways created in the Twenties, and its beginning and end points were Atlantic City on the East Coast and San Francisco on the West, with a total length of 3,228 miles.

The road’s history actually goes back several centuries, and it follows the track of what were once footpaths used by native Americans. The present road lies on top of several older highways, and is a continuation of the National Road, created in 1806 in a law signed by Thomas Jefferson, the third President.

It currently ends near the ski town of Park City, Utah, with Interstate 80 taking its traffic Westwards from there – but US40 serves so many ski resorts as it passes through the Rockies that it can truly be termed a dedicated road for skiers.

Deserted runs through the glades at Winter Park

Winter Park is the most historic of all Colorado’s ski resorts – workers who built the original railroad over the peaks from Denver (it now follows a less giddy route through the Moffat Tunnel) are known to have tried their hand at skiing the slopes in the 19th century. 

The resort opened officially for the 1939-40 season, designed principally as a recreation facility for the people of Denver and owned and operated by the city – an arrangement that lasted until 2002, when Denver entered into a partnership with the Canadian corporation Intrawest, which was itself acquired in 2018 by the Alterra Mountain Company, founders of the Ikon Pass. 

But Winter Park remains Colorado’s longest continually operated ski resort.

It isn’t a glitzy resort with a cute cowboy main street, but has a small town centre, a bus ride from the lifts, with a workaday feel that I rather like.  The pleasant and busy base area of the skiing, known as The Village at Winter Park, has some shops and restaurants and excellent ski-in, ski-out condominium accommodation. 

Winter Park has the best snowfall record of Colorado’s major resorts and, despite its proximity to Denver, is mostly quiet on weekdays. It’s also the leading resort for teaching people with disabilities to ski and ride – about 35 years ago I came here to interview the inspirational pioneer in that field, Hal O’Leary.

The skiing roughly covers the three sectors of Winter Park mountain, Mary Jane mountain and the extreme terrain of Vasquez Cirque. It’s quite a complicated mountain and it takes a while to get to grips with the trail map. But the skiing is magnificent, in extent and variety. There’s a wealth of beginner and intermediate runs, much of it through a park-like landscape, as well as some seriously challenging terrain. 

This includes the Vasquez Cirque steeps of South Headwall and West Headwall and the Alphabet Chutes. And there’s great glade skiing, Black Coal, Medicine Man and Little Raven, from the Eagle Wind lift.

Snowmobile to the top of the world, Winter Park runs in the distance

Winter Park’s communications director Steve Hurlbert guided us over the mountain – and demonstrated that a lengthy stay here is needed to fully explore all it has to offer. Steve also showed us some of the best dining spots, such as Deno’s Mountain Bistro in Winter Park town and the Tabernash Tavern in nearby Tabernash – ‘the best restaurant in the area’.

Mark and Rob on top of the Continental Divide at 12,000-ft

And there was another big thrill to be had. This is high, high country – Mary Jane base is at 9,450-ft. We took a memorable and exciting snowmobile tour up to the top of the Continental Divide, following the old railroad track to Corona Pass at 12,000-ft, with views across the entire Winter Park area and the Fraser Valley. Top of the World indeed!

Useful information

Save money by buying an Ikon Pass. Rob used the Hertz online America Road Trip Planner and he flew Heathrow to Denver with IcelandAir .

Rob skied on Faction‘s latest range of skis whilst reporting for