Boulevard Flea Market

Big Tents

On the western edge of The Hill, along Ella T. Grasso Boulevard, a maze of squat pyramidal awnings presides over a roiling open-air flea market. As plumes of smoke rise from roasting shish kabobs, vendors of fruit, ice cream and slushies sell their rival remedies for summer’s residual heat while other merchants hawk low-priced clothing, accessories, luggage, rugs, toys, CDs and video games (to start). Over it all stands a makeshift observation deck made from two stacked shipping containers, spray-painted with graffiti-style letters that read, among others, “Boulevard Flea Market.”

From here, Chuck Cheslock shows me his market. All 11 acres of it.

Down on the ground, in the walkways between stalls, threads of conversation can be caught, one in Spanish, another Arabic, others Russian or Chinese, and all tied together with various versions of broken English. Vendors hail from Lebanon, Pakistan, Turkey, Jamaica and various African and Latin American countries, among others. “It’s like a League of Nations down there,” Cheslock says.

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And of states. Cheslock once drove into his market and saw license plates from New York, Rhode Island, Massachusetts and New Jersey, all in a row. Speaking about the vendors specifically, he says, “These guys work their asses off. They get here at five or six o’clock in the morning and stay till five or six o’clock at night.”

Cheslock himself is a man who knows how to hustle. Picking through his resume you’ll find as much diversity as there is in his market. He’s worked as an electricity gauge inspector, sold real estate door-to-door and opened his own shops (for tires, flowers and fish, plus a restaurant). “When you start a business, you’re married to it. You eat, sleep and drink it seven days a week,” he says. For the past 25 years, he’s owned the Boulevard Flea Market—which, Cheslock was told upon taking over, has been going for more than 80 years.

Now 71, Cheslock has taken a step back from the market, dedicating more time to his mistress: an all-inclusive deep sea fishing company based in Costa Rica. Now it’s general manager Larry, who prefers to give only his first name, handling the market’s weekend-to-weekend operations. I saw Larry several times flying through the market wearing a wide straw hat and a mustache with the wingspan of a baby albatross, two police officers following in his wake. “The police are necessary,” Cheslock says. “Anything can happen,” though he suggests it rarely does. “During 25 years, I’ve never had a mugging.” According to him, the biggest source of problems is the vendors. Bootleg merchandise is not allowed and Cheslock says vendors are shut down if caught. “We try to be as legitimate as we can,” he says. Designer labels observed at the market, unconfirmed as to their authenticity, include Michael Kors and Chanel.

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Among countless rows of handbags, sunglasses and shoes were some more eccentric items for sale. At one stall, martial arts masters caught swords with their bare teeth and fought over the tops of clouds on a small TV. Laid out on the table beneath were Jet Li action flicks and kung-fu classics like Invincible Armour, Fist of The White Lotus and The 36th Chamber of Shaolin. The deal that day was “1 for $5 or 3 for $10.”

As I walked up to a fruit stand I noticed some strange residents among the usual harvest. The first was rambutan, the southeast-Asian berry, fit for an extraterrestrial fruit basket. It has tentacle-like red hairs that end in curled green tips and is filled with juicy lychee-like meat. Another eye-catcher was the quenepa, a sweet and sour soapberry on the order of a miniature lime. “You suck it,” I was told just as I was about to crack my teeth on the pit.

If you walk around the market enough, déjà vu will hit you often. Like most such markets, vendors tend to repeat themselves. You might find a second fruit stand selling nearly identical bounty to the first, or a second kingdom of colognes rising up on the opposite side of the market, and you can use it to your advantage. Mention that this $30 dollar bottle of Yves Saint Laurent’s L’Homme cologne is $25 on the other end of the market and suddenly the price drops to $20. Hesitate a little more and it becomes $18.

Back on the observation deck, Cheslock looks over the quilt of cultures that blankets his market. He’s considerate of vendors and their amalgamation of cultures, even prohibiting camera use in the market out of consideration for cultural sensitivities to photography. Muslim vendors are plentiful and, after closing, Cheslock allows them to set out rugs and pray towards Mecca. “They’re very religious, and you’ve got to respect it.” His open-mindedness extends to graffiti. “Most people think graffiti artists are just misfits with spray cans, but they’re real artists.” He hired RC Murals, administered by local artist ARCY, to paint the shipping containers overlooking the front parking lot, which sometimes has a long, slow backup of cars looking to enter it from Ella T. Grasso.

Clearly, for many, it’s worth the wait.

Boulevard Flea Market
500 Ella T. Grasso Blvd, New Haven (map)
Sat-Sun 7am-4pm
(203) 772-1447 |

Written by Daniel Shkolnik. Photos 1, 2 and 4 by Daniel Shkolnik. Photo 3 by Dan Mims.

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