After a tumultuous summer, the Lower East Side’s most popular outdoor market, Hester Street Fair, is extending its season into November. Weekends full of vintage shopping, performances, and even a Halloween celebration lie ahead.

“Because we had to reduce our capacity by 75 percent, I didn’t want to keep having to turn new businesses away,” says Janine Ciccone, a producer of Hester Street Fair. “That entirely goes against the point of Hester Street Fair. She and her fellow organizers are working on new tent organization and heating lamps in preparation for colder months.

Because of the pandemic, the weekend fair opened virtually, at first, and didn’t transition to outdoor events until mid-August. Normally, Sundays at the Seward Park lot are reserved for special events — but the Hester Street Fair is using the weekend day to make up for lost time.

To get a sense of this season’s vibe, we visited during the fifth annual Girl Power event, dedicated to the entrepreneurial pursuits of women creators. Olive, a songstress who performs as YungDaddy, guarded the front gate in a neon orange bomber jacket. She checked  temperatures and doled out hand sanitizer while also selling her hand-painted masks, which display various toothy smiles in every color of the rainbow. 

Out of the 30-ish white-topped tents, only three were dedicated to food and two to music —  vendors dominate the rest of the market. Kat Zarra, a Lower East Side local, buzzed with excitement: it was her first time vending at a fair.

“I hope someone asks me to watch over their booth while they go to the bathroom,” Zarra said with a laugh. She fiddled with the seashell-lined lingerie on her table. “I want that. I want us to look out for each other.”

Trixie Encomienda, who runs the apparel shop Don’t Get Caught, sold her original graphic tees a few tents over from Zarra. While they may look like 80s sex ads, the shirts actually reframe the male gaze into Encomienda’s own gaze, as a female artist. The ads aren’t real — but the phone numbers are from old sex ads. (She’s tested all the numbers; they’re no longer in service.)

“Being able to own a brand and make your own living — it means a lot,” said Encomienda. “It’s everything. It’s independence. That’s a really empowering feeling that I get to have.”

The small lot blossomed with barbecue smoke thanks to chef Naomi Lawrence’s Family Affair, a trio of cooks who crisped fresh jerk chicken on the grill. Lawrence had revamped the tented vendor station into a makeshift kitchen. She cooked for the Girl Power event with her mom and dad — Dad on the grill, Mom prepping plates, and Lawrence running the cash register.

“That’s why I called it Family Affair,” she said, handing a customer a plate of food as she garnished it with a hot pink edible flower.

While folks chomped on Lawrence’s jerk chicken and empanadas from Empanada Papa, they were entertained by Olive’s animated Amy Winehouse covers.

“Everyone always gets every shred of the energy I have,” Olive said, preparing for her set. “It dictates my temperament, as far as how much I lose my mind. That tends to be what happens when I pick up a microphone.”

The Girl Power event also featured a one-time-only journaling class. Emily Chertow, who is working to make journaling her full-time job, set up the grassy space behind the fair with crayons, blankets, and stickers. Fairgoers rolled in, relaxed on her pillows, and wrote against the backdrop of the fair.

Plenty of other themed celebrations lie ahead at Hester. This Sunday, Oct. 25, the fair will try to amplify sustainability with a a Progressive Plant Power day featuring local vendor Pat’s Pants and a special curation of progressive brands and artists.

The following weekend, the classic Saturday market will be revamped to celebrate Halloween. Fairgoers are invited to dress in full costume; so they can have their photo taken and sent to a panel of judges. Winners will be spotlighted on the fair’s Instagram page, and rewarded with some crafty donations from a handful of the fair’s vendors.