"Happy Jack” Hollingsworth’s Legacy—His name

The Happy Jack Road (WY 210) at exit 323 on I-80 is a popular back road to Cheyenne.

The views “run Estes Park mighty close for first place” said one Cheyenne traveller in 1921.

An early resident, Jack Hollingsworth, inspired the route’s name. He had a “ranch” estimated to be 25 miles west of Cheyenne, putting it close to the boundary with Albany County. One source says he was called “Happy Jack” because he sang while he worked.  But there are many conflicting stories about him.   

However, by1878 the name “Happy Jack Road” had begun to be used in Cheyenne newspapers to describe the trails Hollingsworth followed to Cheyenne, though the man himself was probably gone. The excerpt below from the May 15, 1884 edition of the Cheyenne Democratic Leader verifies that:

“In 1868 a man named ‘Jack’ Hollingsworth took up a ranch in the edge of the foothills near the present site of the Bowen ranch, and built a ‘dobie’ where he pitched his tent. In a short time after he had located there a saloon was also built and opened….Jack was constantly engaged in hauling wood from the hills. Many stories are told of ‘Happy Jack’ and nearly all of the old-timers remember him. Finally ‘Jack’ sold out and drifted down into the San Juan country and married there. In a quarrel with a party of Mexicans he was shot and killed.”

Possibly by using the Cheyenne Pass route to the eastern plains, Happy Jack Hollingsworth would have had a fairly easy descent into Cheyenne with his loaded wagon. (I erred in the story 2 weeks ago when I suggested that “Cheyenne Pass” was an early name for Telephone Canyon)

It is quite likely that Hollingsworth didn’t actually own the land where he lived and cut wood, which is why he could disappear without much trace.

Ranchers began blockading the Happy Jack Road on the Cheyenne side in 1880 with fences, apparently with no gates. In August 1880, the Cheyenne Daily Sun reported, “considerable ill-feeling is being engendered by the closing of this highway.”

The controversy was finally settled in 1884 when “Mrs. Schalk” and her son George blockaded the Happy Jack Road. It went to court and after their case was settled the Laramie County Commissioners declared it an official county road.

In 1886, Fort D.A. Russell gave permission for the Happy Jack Road (there were no state highway numbers then) to go through the military reservation. Later, 42 miles from Cheyenne, the soldiers from Fort Russell utilized some north-facing slopes along the road for high altitude training—the beginnings of the Happy Jack Ski Area.

By 1933, there was a Civilian Conservation Corp camp at Pole Mountain near the Happy Jack Road. CCC workers further developed the ski trails, built the lodge and probably installed the original rope tow at the ski area. It is unknown who held the first Forest Service Special Use Permit for skiing, but by 1954 it was in the possession of husband and wife Dick and Pat Tobias of Laramie.  In the 1950s and 1960s, UW used it for Physical Education ski classes.

When Dick Tobias was manager in 1954, family season tickets were $25. Night skiing was offered for one dollar in 1962. In 1964 family season tickets had doubled to $50 and Mrs. Tobias was the owner.  The Ski School Director, Dick Hedderman, reported about 500 children had taken classes in 1964.  

The Happy Jack Ski Area was within easy reach of both Cheyenne and Laramie. Its CCC-designed lodge was a delightful place on a winter’s day. One wall of the large main room was a welcoming rock fireplace. It had a big kitchen, indoor restrooms, and it could be rented for parties in summer and winter.

There was a problem with vandalism to the property in summers, an on-site caretaker’s residence was either not occupied continuously, or not at all, and the lodge was lost to fire by 1969.

Then, “People’s Sporting Goods Ski Shalet” in Cheyenne took over, with Joe Jankovsky as the new permit holder.  He negotiated a $45,000 loan from a bank in Laramie, with a Small Business Administration guarantee.  Many improvements were made, including a second T-Bar, 3 new runs, and a warming hut.  The November 15, 1970 issue of the Cheyenne Tribune-Eagle reported that the new owners were all ready, “just awaiting the snow.”

In its heyday the nine downhill ski runs were named “Wood Run,” “Sun Dance,” Lovers’ Leap,” “Bunny Walk,” “International,” “Slalom Run,” “Dutch’s Slope,” “Fall Line,” and the alarmingly named (to skiers) “Rock Island Line.” There were two T-bar lifts and at least one rope tow.  Laramie resident Ann Mullens Boelter recalls that the rope tow wore out mittens “and the right side of our ski jackets as we kids hung onto the rope for dear life.”

The improved ski area was short-lived as apparently Happy Jack did not open for the 1977-78 season and Jankovsky did not pay back the loan he had taken out. Sometime earlier he had sold the ski area to Terry Johnson and Lynn Payne.  The Forest Service revoked the permit in August of 1978 and began wrangling over who would be held responsible for removing improvements and restoring the area. The bank tried negotiations but finally filed suit against Jankovsky in 1980 to recover the loan.

The Forest Service succeeded in getting Payne to pay the approximately $8,000 cost of removing and restoring whatever was left after the caretaker’s residence burned and vandals had made off with much of the equipment. All traces of development were removed and by 1982 the land was restored. Only the still-visible ski runs remain now.

Downhill skiing is a faded memory there, but the Happy Jack and Tie City hiking, biking and cross-country ski trails have been developed instead. All are in the Pole Mountain division of the Medicine Bow/Routt National Forest--on land where Hollingsworth might have cut timber long ago.

Though not much is known for sure about “Happy Jack” Hollingsworth, the 1884 Cheyenne newspaper put it nicely: “the old road which he traveled up and down for so many years still bears his name and will so long as names shall be spoken.

By Judy Knight

Caption: Rope tow at Happy Jack Ski Area’s “Bunny Walk” around 1958. One skier on the right edge is hanging on to the moving rope; two youngsters at center bottom are struggling to get in position. The diagonal line above those skiers is the rope coming back downhill. Photo by Herb Pownall when working for UW Photo Service. Photo courtesy of the Laramie Plains Museum