Sept. 7, 1947 — Aug. 21, 2025
Kenneth Challman was born in Lynwood, California, on Sept. 7, 1947, to Kenneth and Mae Challman.
He was an older brother to Dennis, born in 1949, and Debbie, born in 1952. He graduated from Sunny Hills High School in 1965 and enlisted in the US Navy in June of 1966. He served on a nuclear submarine, the U.S.S. Sam Houston, as a Quartermaster 3rd Class until his discharge in January 1970.
After returning home to California, he attended Fullerton College before moving to Ken and Mae’s property in Shady Cove, Oregon, on the Rogue River in 1972. From here, he commuted to classes at Southern Oregon University (then known as Southern Oregon College). He also tended bar at Omar’s restaurant in Ashland, where he was dubbed “Mr. Shady Cove,” which was eventually shortened to Shady.
He graduated from SOU with his bachelor’s degree in 1988. He attended Phagan’s Beauty School from 1978 to 1979. He worked at a few salons in Ashland before landing at Loose Ends Salon in 1980, where he worked for 8 years before opening his own salon, Shady’s on Fourth, in 1988. He worked 5 days a week, never taking a sick day, until he retired in 2016. This salon was the setting for many talks with friends, much laughter, and meticulous haircuts and styles.
His wife, Sarah Reynolds, was a friend and hair-dressing client for 11 years, until they sparked a romance and married in 1994. In May 1995, their daughter, Phoebe Challman, was born. Shady instilled in Phoebe a love for sports and athletics, a hobby of shopping, that every morning starts with a good cup of coffee, and an exceptional taste in music. When his children were young, Shady was likely to be found on the sidelines of a sports field, pacing, or in the hallways of a gymnasium, also pacing. His children often woke to early morning alarms to participate in runs in Lithia Park, to join him on the slopes of Mt. Ashland, or just to go get a cup of coffee with Pop and his buddies.
Shady participated in many Olympic-distance and half-Ironman Triathlons and concluded his triathlete career at Ironman Canada in Penticton, British Columbia, in 1998, with an impressive finishing time of 12 hours and 28 mins. Thus began the years of more casual (though no less competitive) athleticism, in the form of cycling, running, skiing, golfing, and even short stints of rollerblading, skate skiing, and boxing. Many winter days were spent at Mt. Ashland or on trips to central Oregon with his buddies to ski Mt. Bachelor. His remarkable athletic career finished on the links at Oak Knoll Golf Course, where, undeterred by balance issues, he eventually used a specialized golf cart provided by David’s Chair.
While Shady was diagnosed with Parkinson’s Disease in 2004, he did not let that interfere with his love for athletics and adapted as he needed to over the years to be able to continue his hobbies. He never complained, but persevered and fought back every step of the way. Once he was no longer able to run, ski, and cycle, Shady took up golf. While at first he didn’t consider golf a “real sport because it didn’t get [his] heart rate up”, he soon developed a true love for the “activity.”
Shady was a true Ashland legend, an icon around town, a stranger to no one. He loved his town, adored his friends and family, and enjoyed everything that the outdoors of Southern Oregon had to offer.
Shady died peacefully, surrounded by his family, on Aug. 21, 2025. He is survived and remembered lovingly by all who knew him; most especially, his wife Sarah, his children McKay and Phoebe, his brother Dennis and sister Debbie, and his former wife and dear friend, Toby Dixon.
In lieu of flowers, please consider donating to David’s Chair at davidschair.org, Parkinson’s Resources of Oregon at parkinsonsresources.org, Celia’s House at celiashousehospice.org or End of Life Choices Oregon at eolcoregon.org.
A celebration of life will be held on Oct. 11 at Oak Knoll Golf Course, at 3070 Highway 66 in Ashland, from 4 to 6 p.m. Please bring a side, salad, or dessert of your choice to share as we remember Shady together.
Non-alcoholic drinks will be provided; beer and wine will be available for purchase from Oak Knoll as per OLCC. If possible, please consider carpooling as parking is somewhat limited. Feel free to bring a blanket or lawn chair to sit on, but we will also have tables and chairs.
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