In 1978, Sue Miller was looking to get rid of some old furniture. Longtime Chilmarker and antique dealer Jane Slater suggested she try the Chilmark Flea Market.

Vendor manager Annette Anthony. — Maria Thibodeau

The market, now in its 50th season and affectionately known as the Flea, turned out to be the perfect place.

“I remember making $81,” she said.

“It was a fortune!” added Jane Neumann, who has been a fixture at the Flea for nearly as long as the market has existed, besting Ms. Miller’s 39-year stretch by one year. The two women have stalls next to each other and chat during lulls in their business.

On a muggy Saturday in July, Mrs. Neumann and Ms. Miller reminisced about earlier days of the market, which began in 1967 with five card tables in front of the Chilmark Community Church. The market, organized by Jean Hancock, Gladys Flanders, Julia Poole, Rose Welch, Louise Harris, Hazel Flanders and Dot Smith, started as a fundraiser for the church. Vendor fees still benefit the church today.

“In the beginning, it was mostly things like vintage jewelry, and antiques and things, except for Louise Harris, who sold produce out of her garden,” Mrs. Neumann said.

Helene Rich, right, shares her jewelry. — Maria Thibodeau

The market gradually expanded to incorporate arts and crafts. Over time, it outgrew its Menemsha Crossroad location.

The Flea moved to Middle Road in 2001, where it stayed for seven years. After a one-year stint at the West Tisbury School, it found its current home on North Road, where it has remained since 2009.

Ms. Miller and Mrs. Neumann both agreed that the market’s most significant change over the years is its increased variety of merchandise.

This is in part a concerted effort by vendor manager Annette Anthony, who has run the Flea for the past six summers. Ms. Anthony said she thought the market was lacking a few key elements — food, shade and places to sit were her top priorities.

Now the market is home to a variety of food stands, including Morsel and the Scottish Bakehouse.

Trendy treats like popsicles and kombucha are also for sale. Yommi and Kulture Kombucha are newcomers this year.

Tom Lowe gives a customer a tour. — Maria Thibodeau

And though many stands still operate by the old cash-or-check standby, others have modernized. Of the 89 vendors who rotate in and out of the market’s 66 spaces, Ms. Anthony estimated that 20 to 25 vendors are using mobile credit card readers.

As the market comes up to speed with the age of the iPhone, tradition still holds strong in the rural field off North Road where vendors gather on summer Wednesdays and Saturdays.

Longtime Flea hunter Sarah Lesser-Shavit was looking for a ring — not necessarily new, maybe antique, she said. She and her sister had purchased a few lampshades just a few moments earlier. They have been coming to the market for as long as they can remember — more than 30 years. The sisters even sold lemonade and baked goods at the market from time to time as children. Ms. Lesser-Shavit said, “It hasn’t changed that much, that’s what’s so great. You still have a mixture of old and new.”

“Antiques and artisans, tchotchkes, on and off-Island,” her sister Hannah Lesser added.

“It’s just like a nice Vineyard tradition, like, no time here is complete without one trip to see who’s returned, and what’s new,” she continued.

Debbie Kelly is a Shady Lady. — Maria Thibodeau

For their part, vendors look forward to seeing market regulars too. “The people are great,” Dana Nunes said. “I’ve had some of these customers for almost 26 years, they come back year after year. It’s such a pleasure to see them.”

She continued: “My partner and I, we love to do dinner parties. And it’s amazing how many of the people who just dropped in here unknown have ended up at our dinner table.”

Ms. Nunes is also close with her fellow vendors. “There’s a camaraderie here, if I need to leave my booth for a few minutes I know that I’ve got Gwen over there who’s going to keep an eye out for me, and she knows the same,” she said.

Up the hill from Ms. Nunes, Ms. Miller and Mrs. Neumann presided over their stalls.

In a departure from her start with furniture, Ms. Miller sells glitzy baubles now. Mrs. Neumann has always sold true flea — in other words, antiques.

Joan Davis kept cool under her tent on a hot summer day. — Maria Thibodeau

She had unloaded from her camper a variety of eclectic items. On her table sat a milk glass toothpick holder that resembled a boot-clad foot, a Bakelite napkin ring in the shape of a duck, and a plastic camel with cylindrical salt and pepper shakers for humps.

A curious customer asked Mrs. Neumann about some of the pink glass she had on display. She animatedly began explaining the variations in Depression glass by way of location and manufacturer.

“Would this be the best price for those?” a woman asked about a set of six staghorn handle German steak knives. They conferred about the price and the prospective buyer said she’d take a lap and think about it. She was back within minutes, writing a check for the cutlery and a plate with a bird on it that she’d been admiring.

The sum totaled more than Mrs. Neumann’s own inaugural Flea haul. “I think I made $26. I thought I was rich,” she said.

Ms. Miller’s $81 windfall, by the way, funded an evening out. “I was able to take my family to the Home Port for dinner,” she said. As she recalled it, this was, at the time, the height of luxury.

The Chilmark Flea Market is held every Saturday and Wednesday from 9 a.m. to 2 p.m. off North Road.

More photos from the Chilmark Flea Market.