I remember it like it was yesterday, something that took 50 years to finally occur. It happened on June 23, 2017, two months before my 61st birthday. After five decades of playing one of sports’ most frustrating games, I experienced golf’s Holy Grail.

Finishing an atrocious front 9 at Cape Cod Country Club in East Falmouth that featured four bogeys, two double bogeys and a triple bogey, I arrived at the par-3 150-yard 9th hole. Staring at the very likely prospect of not breaking 50, I lined up an 8-iron, and lofted my ball over a pond fed by the Coonamessett River and toward the green. As the ball cut through the air, one of my playing partners marveled “That’s going in the hole!”

Sure enough, the ball landed on the green, bounced twice, and rolled into the cup. For the first time since first picking up a golf club at the age of 11, I scored a hole-in-one, albeit for a mediocre nine-hole score of 45. Since that day, the 9th hole at Cape Cod Country Club has held a special place in my heart.

Truth be told, Cape Cod Country Club’s course has always been one of my favorites. Not particularly long, its narrow fairways and small greens—best exemplified by the par-4 14th hole—offer challenges to even the heartiest of golfers.

A plaque at the tee box for the 14th hole honors golf’s king, Arnold Palmer. On August 13, 1960, the course, then known as Coonamessett, hosted an exhibition match between Palmer, then the US Open and Masters champion, and future Masters champion Billy Casper.

The 14th is dubbed “the Volcano” for its small, elevated green. The club president at the time, Harvey G. Clauson Jr., bet Palmer $50 that he could not par the hole. Palmer accepted, then upped the stakes, getting Mr. Clauson to agree to $100 if Mr. Palmer birdied the hole. Mr. Palmer, indeed, birdied the Volcano.

Wayne A. Regan of Holliston counts Cape Cod Country Club as his favorite course among the more than a dozen to choose from on the Upper Cape. Mr. Regan cites the 14th and the par-5 6th hole as his favorites.

“It has something for all players which is why I enjoy it,” he said of Cape Cod Country Club. “Players of all levels can have fun and be entertained.”

As for the area’s most challenging course, Mr. Regan mentioned Cape Club of Falmouth, previously Ballymeade Country Club. Sold in 2015 and reopened for play in 2016, the renovation and redesign of the Cape Club “was great,” he said, “and it has multiple challenges depending on the [tee] box you choose to play.”

Neil A. Gleason of Canton also expressed his fondness for Cape Cod Country Club. Mr. Gleason noted that it is “not an overly long course,” and cited its pristine grounds, calling it “very pretty and well kept.”

“Reasonably easy to score if you hit the ball straight,” he said.

As for the Upper Cape’s more difficult and challenging course, Mr. Gleason pointed to Quashnet Valley Country Club in Mashpee. The par-72 layout, he said, “is extremely thick with tree lines and is easy to be out of play.

“Here you better hit straight or go home early,” he said.

Quashnet Valley features one of the Upper Cape’s more challenging par-5 holes, the 18th. A 480-yard risk-reward hole, it features a severe dogleg to the right off the tee. Long hitters can be in position to try and reach the green in two. A wayward shot or one falling just short will land your ball in the Quashnet River, which runs about 50 yards before the green.

At Falmouth Country Club in East Falmouth, visitors have the option of two courses, the 18-hole Osprey Course or the 9-hole Talon Course. PGA general manager Matthew Burgess lauded Falmouth CC as one of the Upper Cape’s “most novice-friendly courses.”

“The Osprey Course is a fun and challenging yet fair course,” Mr. Burgess said. “The Talon is a great course for beginners, ladies and seniors.”

The Osprey Course’s signature hole is the par 5, 516-yard 10th hole, Mr. Burgess said. Similar to the 18th at Quashnet Valley, he described it as “the ultimate risk/reward hole.”

“Eagles are attainable for big hitters off the tee, but not without a challenge,” he said. “Tee shots that stray right will be welcomed by a man-made pond in a setting that two ospreys—the reason for the course’s name—call home, high above the water.”

Of other courses on the Upper Cape, Mr. Burgess called Sacconnesset Golf Club in Falmouth the most difficult. He described it as long and hilly with big undulating greens and many hazards. As for the most scenic hole on the Upper Cape, he pointed to the par-3 125-yard 17th hole at Woods Hole Golf Club.

“The view of Quissett Harbor on the short little downhill par 3 is just breathtaking!” he said.

Former Falmouth selectman and current Falmouth Golf Advisory Committee member Carey M. Murphy cited the par-3 17th at Woods Hole as a favorite of his. Hitting from an elevated tee to a postage-stamp-sized green, he said, calls for the ultimate in focus given “the sweeping vista of Buzzards Bay and the locally famous Knob.”

“I have to concentrate in not finding myself enjoying a one-of-a-kind view,” he said.

Mr. Murphy described the challenge Woods Hole offers golfers as akin to courses he has played in Ireland. The course offers, he said, “a different kind of experience that has the basic elements of risk and reward.”

“Play well and it’s a delight,” he said. “Having a bad day…look forward to the 19th hole. But that’s why we play, right?”

Both Sacconnesset and Woods Hole are private clubs, so to experience their beauty and challenge, a member invite is necessary. The same is true of Mashpee’s Willowbend Country Club and The Club at New Seabury, which boasts two courses, its Ocean and Dunes layouts, as well as The Ridge Club in Sandwich. The Ridge Club is a gated golf community that boasts an enviable roster of residents, including Boston Bruins legends Bobby Orr and Derek Sanderson.

Sandwich also offers Sandwich Hollows Golf Club, a par-71 public course. If time is short, consider Holly Ridge Golf Course on Country Club Road in Sandwich, an 18-hole par-54 course featuring all par 3s.

The time-conscious can also look to Paul Harney Golf Course on Club Valley Drive, off Route 151 in East Falmouth. The 18-holer is a par-61 executive course composed of all par 4s and par 3s. A short drive up Route 28, there is also Falcon Golf Course, a 9-hole gem on Joint Base Cape Cod in Bourne.

Bourne also boasts Pocasset Country Club on Club House Drive, another of the area’s private courses. The 18-hole, par-72 course dates back to 1916, when it was a public track, designed by legendary golf architect Donald Ross. It became a private club in 1989.

Head further north toward the Bourne Bridge to experience Brookside Golf Course, one of the Upper Cape’s most scenic courses. The view from the first tee looks out over the Cape Cod Canal, a view shared by diners at the course’s Sunset Grille patio.

The course is deceptively challenging because it is not long, but it boasts many slopes and sidehill lies. For instance, the second shot on the par 5 10th invariably is played with the ball well above your feet. At the par 4 15th, long hitters off the tee need to be conscious of a pond that guards the front of the green. Even coming up short of the pond, the shallow, 20-foot-deep green challenges even the best golfers’ approach shot.

With more than a dozen courses in the area, the Upper Cape has a golf course to meet the needs of any level of player, from novice to scratch handicapper.