Chip Roper has held eleven jobs in Waterville Valley. He’ll be the first to tell you that — and the first to admit he’s probably not done yet. In this episode of Waterville Unwrapped, hosts Charlie and Ken sit down with the Roper Real Estate fixture to trace a life that has looped through Hollywood, Colorado, and back to the mountains he calls his “comfortable shoe.”
Chip’s roots in the area run deep. His father, a newly graduated dentist, moved the family to Thornton in 1978 to take over a practice in Plymouth — one of just two general dentists in town at the time. After a year, the family settled in Campton, where Chip grew up until around 1990, when his mother eventually moved into Waterville Valley itself. The valley, in other words, was always nearby.
Eleven Jobs and Counting
When Charlie asks whether Chip jumped straight into real estate, the answer is a definitive no. Chip rattles off a roster of past employers that reads like a tour of Waterville’s recent history: bartending at the Coyote Grill, working the kitchen and serving at the Conference Center, stints at Waterville Tennis and Waterville Golf, time at the Schwendi Hutte back when it operated as a full restaurant, and shifts at Video Valley — the video store that once stood where the post office is now. Eleven jobs total, he says with evident pride.
What Chip does not mention is a straightforward path to any of them. After studying theater at UNH with ambitions to act and write scripts, he moved to Los Angeles following graduation. He spent two years there working at MGM — not on the creative side he had hoped for, but as an administrative assistant in home entertainment marketing, helping assemble promotional packages for VHS releases. “It gave me a real taste of what that business actually is,” he tells Charlie and Ken, “and I knew I didn’t want to have it.”
The Vail Years
His route back to Waterville came through his sister, who was working with WVTV Resort Sports Network here. Chip joined her, helping produce a local ski-resort TV show that covered both Waterville and Loon — back when the two mountains were both owned by Booth Creek. The crew would tape a VHS copy of the show and physically drive it up to Lincoln twice a day to air it at Loon. Creative, scrappy, and apparently a lot of fun.
That experience led Chip to audition for a weatherman and co-host position with Resort Sports Network in Vail, Colorado. He got the job and spent six years there — 1998 to 2005 — getting up at five in the morning on weekends to host the show, bartending and caddying on the side, and leaning into a character he called “the Vail Village idiot.” He is notably grateful, more than once, that this era predates the internet.
The Last Ski House
When Charlie steers the conversation toward Waterville’s past, Chip paints a picture of the early 1980s valley: Austrian ski instructors and a young, transient crowd with a distinctly European energy. He believes he may have been part of the last chapter of that era — living on Boulder Path Road around 1997 or 1998, splitting rent four ways at $200 a month, a classic ski house in the old mold.
That ski house is gone now, and so, largely, is the culture that sustained it. Property values in Waterville Valley have climbed by an astonishing 126 percent, Chip notes, making it nearly impossible for seasonal workers to afford to live anywhere near the mountain. Gateway townhouses that once sold for $70,000 now fetch $300,000 or more. The ski bum, he says, is “a dying breed” — and not just in New Hampshire. In Vail, too, the 25-year-old knucklehead with a goggle tan who used to wait your table has largely disappeared.
Charlie connects the housing squeeze directly to a problem he sees every winter: restaurants closing early, businesses running short-staffed, the mountain itself struggling to find workers. He describes his own realization, as an investment property owner, that new norms may be needed — perhaps requiring investors who operate short-term rentals to also provide employee housing. Chip agrees the lack of affordable living is the linchpin holding back the valley’s recovery of that older community energy, even if neither of them has a clean solution to offer.
Always a Foothold Here
Beyond the business talk, Chip shares that his daughter is in the middle of an extensive gap year — Thailand, Vietnam, Bali, Sri Lanka, and, at the time of recording, Italy — and that he was initially opposed to the idea before coming around. He now considers it one of the best things she could be doing. “Her confidence levels,” he says, trailing off with a laugh. She’s a world traveler.
As for whether Chip himself might ever leave Waterville for good, the answer is a comfortable no. He’s come back four times already. He compares skiing the mountain to slipping on a favorite pair of slippers — familiar, effortless, just right. “I see myself always kind of being a part of the valley,” he says. “I don’t know what that is going to be.”
He closes with the motto he and his family have tried to live by: pick up the trash, support everything you can, and let the chips fall where they may.
Listen to the full episode — including more on the WVTV days, the real estate market, and Chip’s thoughts on what it would take to bring the ski-bum era back.