You might not get into the Chilmark Flea Market on your first attempt. The parking lot fills up fast.

When you arrive at the old pasture on North Road, a woman in a pink T-shirt and rubber boots will tell you what to do, either enter or circle back in five minutes. It’s well worth it to return.

The Chilmark Flea Market, the primary fundraiser for the Chilmark Community Church, is now in its 55th year of operation and busier than ever.

Danielle Mulch of Archil Designs — Ray Ewing

“It has grown in leaps and bounds,” said Annette Anthony, the lady in the pink shirt, who has been Chilmark Flea’s vendor manager for the last 17 years.

What began as a gathering of congregation members peddling attic antiques has become one of the Island’s largest artisan and antique fairs.

“The field is just magical,” said Ms. Anthony of the market’s setting.

It is the archetypal old Island pasture, where birds and dragonflies dance amongst sparse old cedars providing shade to the luckiest vendors. The setting is complemented, Ms. Anthony said, by a true community feel: “We have an extra emphasis on kindness, camaraderie and working together; people will help jump each other’s cars.”

Angela Sison of Conrado clothing. — Ray Ewing

“It’s been a really nice introduction back into the Island community,” said

Phoebe Kelleher, a new vendor at the market this year.

She and her partner Lizz Flynn returned home to the Island from Vermont to start Junie B’s Bakery (named after their dog, June Bug). While their blueberry coffeecake is always the best seller, Ms. Kelleher said her favorite item is their cheddar jalapeño biscuit.

Ken Roache is another freshman marketeer, selling bags of his homemade jerky at the Ken’s Vineyard Kitchen stand. “I was a chef in a past life,” said Mr. Roache. “I’ve been making jerky for 20 years but I had never written anything down. It’s always been a pinch of this and a poke of that.” He smokes his beef jerky with a combination of hickory, pecan and Island oak, and grows his own garlic for seasoning.

New vendors aren’t unusual at the market.

“It’s a constant rotation,” said Ms. Anthony, who acknowledged the market’s shift toward more artisan goods. “I try to make sure that it never loses that flea market component.”

Each market has space for up to 60 vendors, and spaces are seldom left unfilled. If a vendor can’t make it one day, Ms. Anthony calls one of the vendors on the market’s waitlist to fill in. This, combined with a different roster for the Wednesday and Saturday markets, means that visitors are bound to find something new on each trip.

But some vendors are in it for the long haul. Dana Nunes and Jane Neumann have been at the market for 31 and 45 years, respectively. Celeste Santee, who has been in the antiques business for 30 years and at the market for nearly as long, said she tries to preserve some of the market’s “old country store” feel with her stand.

“Every item tells a story,” she said of antiquing’s enduring appeal. “I love the intrigue of what each object is and who created it and why.”

One of her favorite market activities is getting her customers to guess the purpose of some of her stranger-looking tools. No one has yet guessed the correct use for the large, two-pronged fork she has out on her table.

Vendors at the Chilmark Flea sell everything from kombucha to jewelry, from old books to handmade clothing. The market has doubtless changed since its early days, Ms. Anthony said, but the flea market spirit is still alive.

“I try to keep that variety, a little bit of this, a little bit of that,” she said. “That’s what a flea market is: bric a brac.”

Chilmark Flea occurs every Saturday and Wednesday 9 a.m. to 2 p.m. at 142 North Road, Chilmark. Spaces fill up fast. For more information, visit