The wind is your friend when you’re sailing on Stockton Lake, Missouri’s premier sailing lake. With more than 25,000 acres of pristine water and 300 miles of shoreline, it’s the perfect place to make a run and take in the sights.

Each spring, Joe Pyles anticipates the feeling of warm wind against his face. As he awaits the arrival of sailing season, Joe writes poetry. One of his poems begins, “Waiting out another land bound season, older each year my patience has some unsteady fear …”

Joe and his wife, Carol, both retired, live in rural Greene County where they are just 50 minutes away from their favorite place to sail: Stockton Lake. Missouri’s premier sailing lake offers 25,000 acres of pristine water surrounded by 300 miles of unspoiled shoreline.

According to Joe, “Stockton is one of the top 10 sailing lakes in the United States. Since no one is allowed to build a home along the shore, the water stays exceptionally clear. There is plenty of room for turning a sailboat, and the wind blows nearly every day.”

From April through November, Joe and Carol spend two or three days at a time sailing on Stockton Lake. Their immediate social group—10 or 12 couples who also have boats­—gather on the dock after a day on the water. “There are some really good storytellers in the bunch,” Joe says.

Joe’s sailing experience began in the 1980s when he was on temporary duty with the Army National Guard at Corpus Christi, Texas. Boat races (regattas) between soldiers and sailors took place daily. But it wasn’t until 1996 while vacationing in Door County, Wisconsin, that Joe became serious about the sport.

“I decided to take a walk near Lake Michigan to look at the boats,” he recalls. “A guy asked if I wanted to take a ride, but his price was too high. He wondered whether I knew how to sail and offered three days of lessons for both me and Carol. When he threw sack lunches in on the deal, I said ‘yes.’ Carol could not believe that without her knowledge I signed both of us up for sailing lessons. She did, however, turn out to be the better sailor, and those sack lunches were really big.”

Dissatisfied with two smaller sail boats over a 10-year period, Joe and Carol bought the Arabesque in 2015. Their pride and joy, the 40-foot Catalina is named after a ballet position. When all conditions warrant this incredible one-legged stance, Joe does his rendition of it at the boat’s forward end. It is similar to a fancy radiator ornament on an antique automobile, and not quite as picturesque as the Titanic movie scene.

A good sailing day at Stockton Lake begins with a casual breakfast at the dock until around 9 o’clock. One tipoff of correct wind velocity is a particular tingling sound as it blows through the mast lines. Under diesel power, the Arabesque chugs slowly out of the harbor before the engine shuts off and sails are raised. Silently, except for splashes against the forward hull, the craft begins to move across the water.

As fog lifts, there is the distant call of a loon. Turkeys exchange gobbles in the opposite direction. Bald eagles soar overhead while flights of migrating geese fly even higher. It’s still early enough to see deer drinking at the water’s edge.

Throughout the day, the boat makes 10-mile sailing runs (reaches) with the wind, then tacking back-and-forth runs against the wind. After hours of fun, the sailboat has made minimal ecological impact on the earth. The only carbon footprint comes from the diesel engine while backing up the boat and moving it out of the harbor. The Arabesque burns about 3 gallons of fuel in a year.

Joe and Carol enjoy sitting in their boat at East Sunset Cove as the sun drops over the horizon. After a few mystical moments together in the twilight, they sail back to the dock and gather with friends for storytelling.

As prizes for charities, Joe and Carol offer outings on the Arabesque. Most winners have never been aboard a
sailboat, but Joe says one woman from Kansas City had enough experience to actually be helpful on her day trip around Stockton Lake.

The Lake Stockton Yacht Club hosts regattas every month throughout the sailing season. Visit the group online at

If You Go

Stockton Lake is about 10 miles northwest of Greenfield, off of Route Y and state Route 215. The area has several marinas, resorts, and campgrounds. Find out more at and

Show-Me More

Several Missouri lakes offer sailing potential. Check out the opportunities at Smithville Lake, just 20 miles from downtown Kansas City. Paradise Point Yacht Club has the lowdown on Smithville sailing lessons, regattas, and social events. Get acquainted at

Odyssey Sailing School is a St. Louis-based American Sailing Association-certified mariner training program led by Captain Bob Weber, who offers a range of courses for novice and experienced sailors alike. Learn more at

Article originally published in the May 2019 issue of Missouri Life. It was updated in May 2024.