In April 2014, Craig’s phone rang with an offer he hadn’t expected — at least not for another eight years. Back when he was 50, he’d joked with Tom Corcoran and Bill Cantlin that if they ever thought about selling the Waterville Valley Golf Course, they should give him a call. He didn’t think much of it. Then, on April 3rd, 2014, the call came.
Craig was 58, at the peak of a sprawling real estate career with rentals, development, and operating businesses spread across Cape Cod. He’d imagined doing something like this from 60 to 80 — a final venture he could sink himself into. Two years early wasn’t the plan. But the older mentors he consulted pushed him forward. “We waited too long to sell our businesses,” they told him. “If you can do something like this and you’re comfortable with it, go for it.” He went home, spent the better part of a year and a half liquidating his entire real estate operation, and went all in.
Craig’s connection to Waterville actually stretches back to 1978, when he arrived fresh out of college to work group sales at the ski area — wrangling buses full of college kids. He made lasting friendships that season, including with Jeff Brown, and stayed loosely tied to the valley for decades, buying and selling condos and houses along the way. He left the full-time scene in 1980 because, as he puts it plainly, there wasn’t enough business to build a career on. The heydays people romanticize, he says, were really just a lot of young people drinking and eating out. “Tom Corcoran was 32 when he came here. Bob Fries was 28. They partied well.” Now they’re all 70, and the dynamic has simply changed — not for the worse, just differently.
A Builder’s Touch on the Fairways
Craig runs the golf course the way a builder would: he mows it to his own game, moves trees that get in the way, and reshapes things gradually and deliberately. Host Charlie has noticed — he tells Craig that residents constantly comment on how good the course looks. Craig shrugs it off a little. “It feeds on itself,” he says. “When people thank you, you just want to do more.”
The improvements are tangible. He’s softened the course, adjusted cart paths, and enlarged irrigation ponds to capture more natural water runoff from the surrounding hills. The ninth green has a percolation problem he plans to eventually address properly — glacial till underneath that needs to come out and be replaced with stone, sand, and loam. The eighth green, an old crowned design, he’s been quietly “scrunching” to the right by a foot a year for the past decade, moving it nearly eight feet without ever ripping it up.
The most distinctive feature on the course, Craig explains, is the seventh green — the oldest on the property, over 70 years old, and still planted with a variety of velvet grass that’s no longer commercially available. It looks different, rolls differently, and catches the light differently than the bentgrass on every other green. Craig waters it ten minutes longer per day to keep it healthy. He thinks there’s a similar old-grass green up at a course in the Gorham–Lancaster area, but he couldn’t place the name. The only other notable characteristic: hole-in-ones happen with surprising regularity — three or four per summer, often by women, who get the dated flag from the hole as a keepsake.
Ice Cream, Tubing, and the Art of Staying Busy
Craig freely admits the one thing that changed after buying the golf course was his plan to have winters off. Instead, he now runs the tubing hill for 46 days each winter — a lean, adrenaline-driven operation that works specifically because of the golf course’s long, flat run-out. Ski areas tried tubing and ran into trouble when tubes hit parking lots or base lodges; Craig’s setup gives tubes room to stop safely. He calls it the weirdest business he’s ever run, but a pretty cool one.
This summer, he’s also expanding the ice cream shop in earnest. He sources what he calls “Island Ice Cream,” a small-batch product from a Vermont creamery, and plans to open for full summer hours — Thursday through Sunday in July and August, with lighter weekend schedules in June and September. “I like doing it,” Craig says, “plus I like ice cream.” It’s a natural fit, he adds, for a town that’s increasingly a destination for grandparents bringing grandchildren up for the summer.
The Thursday night member scramble has become a genuine social institution, non-competitive and well-attended. Craig jokes that he has to practically beg people for their scorecards. He’s also adding pickleball to the general membership this season, with a limited guest pass policy — his definition of a guest being a college friend visiting from out of town, not a neighbor who’d rather not join.
Bullish on the Valley
Craig’s most compelling observations come when the conversation turns to Waterville’s future. He’s watched Cape Cod transform in his lifetime from a cheap summer escape into a year-round community with the hospital as its largest employer. He thinks Waterville is on the same arc. “I call it a town with resort amenities,” he says. “The resort part never really worked” — and he points to Tom Corcoran himself as evidence, a man who was always dreaming bigger than the business could support.
He’s skeptical of the gondola proposal, viewing it primarily as a real estate play. He notes that three holes were removed from the golf course in 2005 to make way for the Moose Run subdivision and Green Peak condos — and 20 years later, the land still hasn’t been developed. That reduction in the course nearly killed the club entirely; falling membership and declining revenue pushed Corcoran toward closure, which is ultimately why Craig got the call.
The broader trend he finds encouraging: new buyers are using their condos and homes in both summer and winter, something that simply didn’t happen before. The year-round registered population has grown from around 200 to approximately 740, with Craig estimating the true functional number is closer to 1,000. “If we get another 500 people in here,” he says, “you’re dividing the wastewater treatment plant cost by 2,000 instead of 1,000. It’s just math.”
For younger people wondering how to make a life in the valley, Craig has a direct answer drawn from his own model: combine things. Golf alone, food and beverage alone, tubing alone — none of it works. Together, they do. “You might have to have three jobs up here,” he says, “but you can make 60, 70, 80 grand.”
His philosophy on failure is just as direct, passed down from his grandfather: “There’s nothing wrong with sinking the ship. Just get on another boat — maybe a bigger one.”