Leon Oliver stands by the entrance of Sheepscot Links, the golf course he co-owns with his wife, Alicia. (Mic LeBel photo)
Leon Oliver has deep family roots in Lincoln County, but he became a golf snowbird migrating back and forth from Florida to Maine for decades to accommodate his career as a professional in the golf industry.
“Now he’s in Maine full time at his own golf course living the dream,” joked Alicia Oliver, his wife of almost 30 years and co-owner of Sheepscot Links in Whitefield.
The Olivers purchased Sheepscot Links in 2019, and have put their full energy into sprucing it up and making it a fun, affordable golf experience for the local community.
“Annual memberships have risen from 94 to 225 since we bought the place, so we must be doing something right,” Oliver said.
He may be new to golf club ownership, but Oliver is a true legend of the sport in Maine. He’s won two Maine Chapter Championships in 1998 and 1999 and the Maine Chapter of the Professional Golfers’ Association Player of the Year Award in 2017. In 2022, he was inducted into the Maine Golf Hall of Fame and the Lincoln Academy Sports Hall of Fame. Oliver earned his PGA pro credentials three decades ago, and holds single round records at five courses in Maine and Florida.
Despite his lofty achievements, TimePPPPPOliver has followed a blue collar pathway into a sport that’s sometimes perceived as being for the rich and privileged.
“I still remember how one of my baseball buddies got me into golf when I was 10, and I’ve loved it ever since,” Oliver said. “When I was 11 I got a job at a course moving sprinklers around, which allowed me to play for free. I’d pack my lunch in the morning and work and play golf there all day and wouldn’t get home until dark.”
He also got a job at Wawenock Golf Club in Walpole while he was in high school, and could play for free after work.
“We try to help young kids start golfing at Sheepscot Links by letting those under 15 play for free.”
As a kid, Oliver liked how golf would pose a new challenge every round, and how it was different from the team sports he was playing.
“It was just me against the golf course,” Oliver said.
All of Oliver’s practice as a youngster paid off in high school when he made the Lincoln Academy golf team. Oliver was a standout on the squad and qualified for the state championship three out of four years, earning fifth place his senior year.
His full-time golf lifestyle began after graduating from Lincoln Academy in 1982 and playing golf at the University of Southern Maine where he earned All-Conference honors his freshman year.
“College was a lot of fun, but school just wasn’t for me,” said Oliver. “I had to go out in the world and do something, and golf was that something.”
Oliver left USM in 1983, and got a job at the Gasparilla Inn where he could start his career by completing the PGA’s four-year program to become a pro. The golf resort, in Boca Grande, Fla., also fulfilled his desire to play golf year-round.
For many of the 20 years he worked at the Gasparilla Inn, Oliver also had a bunch of side hustles to make money when the golf course slowed down including as a bartender and a maitre d.
“I had a paper route when I was little and I’ve always liked to work, so I would just do what was available to keep me busy around the club where I could keep playing golf for free,” said Oliver. “The club also provided housing, so it was a good lifestyle for a young fella.”
The Olivers may be living Leon’s golf dream now, but for many years the couple was living a nomadic golf pro lifestyle in two regions of the U.S., which posed some challenges, especially when they were raising their children, Malcolm and Mallory. Years later, Malcolm Oliver developed his dad’s golf passion and earned many accolades of his own in high school, college and as a pro. Malcolm Oliver won the Maine Class B championship in 2011 and is now an accomplished PGA golf pro in Massachusetts.
Of the 30 or so years Leon Oliver worked in Florida, he only lived there full time for five years. Most summers he migrated back to Maine to be a golf pro at Wawenock and the Bath Golf Club. During many of his years at Wawenock, Oliver coached the Lincoln Academy high school golf team.
There was a good reason for the Oliver family’s typical biannual migration.
“Unfortunately, you can’t make a living and support a family just working as a pro during the summer in Maine,” said Oliver. “Now, we’re giving the golf club ownership thing a go, and so far we’re doing pretty good. It’s hard work seven days a week during the season and then we recharge ourselves during the offseason from about December to March.”
Running a golf club in rural Maine is not a slam-dunk to be a lucrative endeavor, so for now it’s all hands on deck to keep the dream alive and prospering. Oliver does a little of everything, and one of his favorite tasks is lawn care and maintenance of the course.
“I love mowing, it’s very therapeutic,” said Oliver. “I also grind the reels, and sharpen the blades. I maintain the equipment and fix whatever needs to be fixed. I like to keep busy.”
So does his wife, who also has local roots and graduated from Lincoln Academy in 1989. Alicia
Oliver staffs the clubhouse, does the books and performs a long list of non-golf tasks behind the scenes.
At almost 60 years old, age and associated injuries may have finally caught up with Oliver’s penchant for elite golf competition, but don’t count him out just yet. Despite having a hip replaced about 15 years ago, and the other one telling him it may be ready for the same, he wouldn’t commit to completely closing the door on competing in future tournaments. For now, being hobbled by injuries has helped him focus even more on the golf course and business.
Oliver admitted he’s still adjusting to not being a golf snowbird and dreads the potential for a golf-less winter in Maine. The couple has plans to go to Texas to warm up and unwind, but other than that, Oliver says his focus is already on the 2024 season for Sheepscot Links and keeping the course ownership dream alive and kicking.
It’s clear that golf is at the very core of Oliver, and that being injured and not able to play his beloved sport is like an itch he can’t seem to scratch. When pressed on his hobbies outside of golf, he pondered the question for a bit. Oliver highlighted family and travel, but pivoted back to something golf-related.
“There’s plenty to do here in the offseason to keep me busy,” said Oliver. “We’re looking at turning a course-side home on the eighth hole into a clubhouse and that requires a lot of planning.”
Oliver enjoys living in Lincoln County full time, but admitted that he misses going south to avoid the cold Maine winters.
“Being a golf snowbird again is a potential dream for the future,” Oliver said.
With a new grandchild expected next month, however, Oliver noted that family comes first.
“We are excited about the birth and want to be part of their life, so warm Florida winters will have to wait a while,” he said.
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