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Bib and Jaime Mills on board Jamie’s boat in Greenport. (Credit: David Benthal)

Hanging on the wall in Jamie Mills’ Greenport office is a piece of paper with two options for a slogan billing Wm. J. Mills & Co. as America’s oldest family owned and operated sailmaker.

Mills peers over the two choices, which feature very subtle differences, and can’t quite seem to decide.

“I think I like option A,” he says.

His brother Bob, seated across from him, cracks a wry smile.

“Funny, I think I like option B,” he says with a chuckle. 

These are the types of interactions you might expect from colleagues who have spent nearly 50 years of working alongside each other. In the case of the Mills brothers, they have the added distinction of running a business that bears the family name and has been in existence since the latter part of the 19th century. The company counts its arrival in Greenport in 1880 as its start, but Jamie believes the sailmaking business may have started more than a decade earlier elsewhere on Long Island. “I think 1880 just rolled off the tongue a little better,” he said.

William J. Mills

For about two decades the company has been considered America’s oldest sailmaker, but the recent sale of the Claudio’s restaurants has also made it Greenport’s oldest family-owned business — a distinction  it shares with Preston’s Chandlery, which also counts 1880 as its first year.

To accomplish this feat, generations of the Mills family have adapted many times over, from sailmakers  to oystermen to manufacturers of awnings and all things canvas.

Its many endeavors are mostly tied together by one single thread (if you’ll pardon the pun): the sewing machine.

To this day, it remains a fairly labor-intensive operation, as staffers enter the workshop and, seated behind industrial grade sewing machines, carefully stitch together pieces of canvas that become boat covers, tote and duffel bags, seat cushions and more.

The awnings at Shinnecock Hills Golf Club, where the U.S. Open was played this summer, are Mills made. So are some of the cushions on shoe benches at places like Foot Locker.

Although canvas sails are just a small part of the business today,  they are perhaps what the company is best identified with — and certainly where it got its start. Wm. J. Mills’ original Greenport sail loft serviced the village’s booming commercial fleet. The family has since established deep roots there. The Mills brothers are Greenporters through and through, snickering at the mere thought of someone from their family living in such a place as Southold and proudly proclaiming they were both born at Eastern Long Island Hospital in the 1950s.

But operating a sailmaking business in Greenport hasn’t always been smooth sailing.

By the 1920s, the introduction of steam- and gasoline-powered engines forced the company to adapt along with the changing dynamics in the village it served, and while they continued to produce sails for recreational purposes, Mills established the Cedar Island Oyster Company, which was run by his son, Capt. Robert L. Mills.

After William’s death in 1940, the canvas business continued to diversify as awnings were added to its repertoire.

The Wm. J. Mills display at the East End Seaport Museum in Greenport. (Credit: Grant Parpan)

Robert’s son Bill Mills, Jamie and Bob’s father, is credited with establishing the company’s decades-long relationship with Boston Whaler. For more than 40 years, Wm. J. Mills & Co. had been the sole supplier of canvas for the top boat manufacturer.

Asked if it’s foresight or just necessity that has helped the company find new avenues to drive business and survive more than 135 winters with a mostly seasonal operation, Jamie points instead to something else.

“We have been smart, but also pretty lucky, if we’re being honest,” said the company president, whose given name is William J. Mills III.

An architect who once walked in cold to the Mills showroom ended up leading the company to install awnings at the Marine Terminal at LaGuardia Airport, a job that Jamie estimates brought in $40,000 at a time the business really needed it. In another fluke encounter, a Southold resident with connections at NBC once led the company to do canvas work for the sets of televised bodybuilding competitions.

The Mills enterprise once occupied the building at the southwest corner of Front and Main streets, but for  30-plus years has sat on Route 25  at the western edge of Greenport. A walk through the facility reveals decades of family history. There’s a portrait of Robert Mills I in his World War I uniform and an enlarged magazine cover in the showroom featuring Jamie, Bob and Bill.

Bill Mills, who dedicated nearly 70 years to the family business and oversaw some its biggest successes, passed away two years ago, but his office remains largely untouched. A stack of crossword puzzles he completed over the years sits a couple of feet high on his desk.

“I still can’t bring myself to get rid of any of this stuff,” Bob said.

How could he? Every fabric in this canvas business connects the Mills family to a legacy they’ve built in Greenport and through boats that travel the world over.

Last year, Bob’s son, Robert III, joined the company’s leadership, marking a fifth generation of Mills men and women making sails and more on the North Fork. Each day he enters a building where a sign still hangs bearing his great-great-grandfather’s name: Wm. J. Mills Sails & Awnings, Est. 1880.