From Cheshire Cat Grins to Cannonball Bumps: My Favorite Names on the Winter Park Trail Map
What’s in a name? If you’ve skied Winter Park Resort, you’ve likely noticed that the names of the ski runs are (quite literally) all over the map. From Jabberwocky to Derailer to Balch, there’s a method to the madness - and they make for great lift conversations!
From runs in the Eagle Wind Territory paying homage to the Indigenous land the resort sits on, to silly, tongue-in-cheek names like Drunken Frenchman, to a host of runs inspired by Alice in Wonderland, there’s no shortage of names to talk about and speculate on their roots. At Winter Park, a run name might have come from a founder’s whim, have grown organically from ski patrol or die-hard skiers, or be the result of a marketing committee think tank. However names were born, each one means something to the people who know the ins and outs of Winter Park Resort, and there are so many that make me smile.
As we get a little more snow and more runs open up, I thought it would be fun to put together a few of my favorite run names as well as the history behind them!
Cheshire Cat
Every time I ski Cheshire Cat, the mischievous grin of Alice in Wonderland's infamous cat comes to mind. Not only do I love the quick blue/black ski down to the Olympia lift, I love the playfulness of it and all the run names surrounding it. March Hare, Mock Turtle, Mad Tea Party, White Rabbit, Dormouse, Jabberwocky, Tweedle Dee + Tweedle Dum, and even the 55-year-old, two-seater Looking Glass lift all give a nod to Lewis Carroll's famous children's novel. It turns out that Steve Bradley, one of Winter Park Resort's founders was a big Alice in Wonderland fan and helped name those primarily green/blue runs on the Winter Park side. Skiers might not even notice the whimsical names and their theme, but I hope you can make the connection next time you're skiing the Park side!
CANNONBALL
Most of the classic Mary Jane bump runs date back to the 1970s, when Mary Jane first opened and the culture was playful and not-just-a-little irreverent. Trail names were often coined by ski patrol, mountain crews, and locals - usually inspired by how a run actually felt skiing it. Enter: Cannonball. The name says it all. With its steep pitch and relentless bumps, you drop in and feel like you’ve been shot straight out of one.
As Mary Jane celebrates its 50th birthday, it’s fun to look back at those early days when so many of the names were born. Outhouse, Sober Englishman, and Drunken Frenchman reflect the mountain’s tongue-in-cheek personality, while Railbender, Runaway, Derailer, Boiler, Brakeman, Needle’s Eye, and Trestle nod to both the way the run makes you feel as well as the railroad culture that helped shape the Fraser Valley. The trail names on the Mary Jane side don't just mark the map: they tell a story.
DILLY DALLY ALLEY
It really rolls off the tongue - and it’s a favorite with the younger ski crowd. Kids finish with ear-to-ear grins, while parents run the numbers on how many years skiing it just took off their knees. With small jumps and rollers weaving through the trees, Dilly Dally Alley is a short spur trail that feels like a natural roller coaster.
To “dilly dally” means to wander or play around instead of heading straight for your destination, which couldn’t be a better description. It’s not steep; it’s not serious - it’s more of a frolic through the woods. The kind of run where you stop, laugh, take a beat, and just enjoy the ride. One of those trails named purely for how it makes you feel.
You might've even seen the sticker that says, “Don’t Groom Dilly Dally Alley,” a playful nod to the classic “Don’t Groom Mary Jane. – God” sticker found on more than a few lift towers and helmets. Kid or not, it’s worth taking a lap on Dilly Dally Alley just for the fun of it.
ACES AND EIGHTS
A quick glance at the trail map shows a host of names that reference those “Wild West” roots from the early days of homesteading and settling in the Winter Park area. Miners, rail yard workers, and loggers began settling here in the late 1800s, and that history still shows up all over the mountain. Trails off the Wild Spur Express lift (formerly the Pioneer, or simply “Pio” to many) give a nod to the Wild West with names like Shootout, Quickdraw, Sundance, Stagecoach, Buckaroo, Gunbarrel, Chuckwagon, and Gambler. On the Jane side, Gandy Dancer, Golden Spike, Narrow Gauge, Sidetrack, and Sluice Box pay homage to the area’s railroad roots. And over on the Park side, Switchyard and the famous terrain park, the Railyard, do the same.
But my favorite name in the bunch of “Wild West” trails is Aces and Eights. It just has a fun ring to it, doesn't it?! A clever nod to the gambling and poker culture of Wild West saloons, Aces and Eights references what’s known as the “Dead Man’s Hand”: two black aces and two black eights. The hand became legendary in the Old West, named after Wild Bill Hickok, who was reportedly shot while holding that very combination. If you want to check it out, you can hop on just off the Wild Spur Express lift and ski the playful little bump run that connects you back to Lonesome Whistle.
OVER 'N UNDERWOOD
One of the things I love most about skiing at Winter Park Resort is how many of the trail names are tributes to the people who helped shape the mountain. Cranmer honors George Cranmer, often called the father of the ski area for his vision in bringing Winter Park to life. Allan Phipps and Bradley’s Bash celebrate early leaders and trail builders, while Jack Kendrick and Over ’N Underwood recognize key contributors to the resort’s growth and lift development. Mulligan’s Mile (a surprisingly fun bump run) was named for the caretaking spirit of Dick Mulligan. Retta’s Run honors a volunteer who helped make skiing more accessible as an early pioneer for the NSCD (National Sports Center for the Disabled), and Engeldive pays tribute to a founder of the ski school. Balch remembers one of the resort’s first managers, and Bill Wilson’s Way reflects the passion and teaching legacy of an instructor who helped grow beginner terrain. And the Mary Jane Trail, a shoutout to Mary Jane who owned the land Mary Jane Territory sits on, rounds out a lineup of runs that aren’t just fun to ski - they’re stories woven into the mountain itself.
Over ’N Underwood might be one of the most cleverly named, legend-inspired runs on the mountain, and it easily makes my list of favorites. George Underwood started at Winter Park in 1951 as head of lift maintenance. A gifted welder and overall machine-master, he oversaw the nearly every mechanical element at the ski area and helped create the first snow grooming device, the “Bradley Packer.” By the time he retired in 1972, he had built every lift and tow on the mountain. The trail named in his honor gives credit where it's due - a fitting tribute to his more than 20 years of service that quite literally helped build the place from the ground up.
FORGET-ME-NOT
Several runs off the Sunnyside and Panoramic Express lifts fall in with a mountain wildflower theme. They were named in honor of Charles Parry, a well-known area botanist, and his wife Eva, with Forever Eva likely referencing Mount Eva, that hard-to-miss peak on the Continental Divide you can see from the bowl. Names like Edelweiss, Bluebell, Columbine, Paintbrush, Kinnikinnick, Juniper, Primrose, Lupine, Larkspur, and Sky Pilot are all perennial wildflowers native to high-altitude Rocky Mountain slopes, appropriate for runs that sit among the highest points at Winter Park Resort.
With a clever double entendre, Forget-Me-Not is named after the bright blue wildflower whose alpine variety grows above 10,000 feet. Fittingly, Forget-Me-Not the run sits in Parsenn Bowl, accessed off the Panoramic Express lift, with a summit at 12,000 feet. Not only does the name stick with the wildflower theme and nod to the beauty of the high alpine, but the panoramic views of the Continental Divide are pretty unforgettable: truly “forget-me-not” worthy.
THUNDERBIRD
The Eagle Wind Territory first opened during the 2006–2007 winter season and was inaugurated with a traditional Arapaho blessing ceremony to honor the land. The trail names were chosen in collaboration with Northern Arapaho Tribe Elders as a tribute to the tribe and the Indigenous roots of the area as the Cheyenne, Ute, and Arapaho peoples all have ancestral ties to the land on which modern-day Winter Park Resort sits. “Eagle Wind” is the Arapaho name for that land, and you can learn all about the history behind the run names (all translated into Arapaho on their signs) in Eagle Wind here. Situated on the back side of Parsenn Bowl, the runs in Eagle Wind (accessed from the Panoramic Express and Eagle Wind lifts) are known for their expert-level (read: all black diamond) steeps and tree skiing.
Of all the names off the Eagle Wind, my favorite has to be Thunderbird. It just sounds strong, intimidating, and a little wild, doesn’t it? The Thunderbird is a common myth among the Arapaho. Said to create lightning, thunder, and bring storms, the Thunderbird is a symbol of power and strength. And the run named after it is no different! Thunderbird is a black run off the Eagle Wind lift and the longest marked trail in that territory. It winds through gladed, natural terrain and feels closer to in-bounds backcountry skiing than a typical resort run. Most of the skiing here winds through trees on natural snow rather than groomed runs. Natural, wild, and a little bit like a storm! It’s a beautiful stretch of terrain, and both the territory and its trail names honor the Indigenous peoples who have deep ancestral ties to this land.
IS WINTER PARK CALLING YOU HOME?
If you’re ready to ski Winter Park Resort as often as possible, sneak out for a few runs on your lunch break, and know the trail names inside and out, owning property in Grand County might already be on your radar. I’d love to share not only my favorite run names with you, but also the ins and outs of investing in mountain property here in the Winter Park area. Reach out to schedule a buyer’s consultation and learn more about the real estate opportunities waiting for you in Grand County!
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