New business owners are looking to keep shops open deeper into the off-season. — Ray Ewing

With many of its iconic shops closed and summer crowds long gone, the Gay Head Cliffs have become an unlikely setting for vibrancy in the off-season as a determined few shopkeepers work to extend their seasons deep into the fall.

“It’s more of a second season, if you want to call it that,” said Del Araujo, owner of Aquila, a coffee and gift shop.

On a recent afternoon, the wind whipped over the Cliffs and across Aquinnah Circle as Mr. Araujo tended to his shop, preparing to open for the weekend. Already this fall, Mr. Araujo has found success in hosting a themed scavenger hunt the day before Halloween where kids and adults went on a search for “Moshup’s treasure.” Mr. Araujo said the event served as an attraction to the Cliffs in the off-season and a way to share tribal history and culture.

Making it festive for the holidays. — Ray Ewing

“What we really want to do is start bringing in more of these events,” Mr. Araujo said. Looking ahead, Mr. Araujo said Aquila will remain open on weekends throughout the holiday season. He and his family recently set up a cornucopia of Christmas decorations, lining railings at the shops with lights and dressing Aquila up with a wreath and festive ornamentation.

“We’re definitely having fun, I’ll tell you that much,” Mr. Araujo said.

While decorating on Sunday, Mr. Araujo made the rounds of the other shops at the Cliffs, catching up with shopkeepers and offering to decorate stores in between stints of carrying boxes of lights into his shop.

Across the path at On the Cliffs, a clothing and gift shop, owner Amera Ignacio braved the weather in a long coat and knit cap. She said her shop usually stays open into November, adding that the change in pace from summer to fall is always welcome after a busy season.

Amera Ignacio at On the Cliffs. — Ray Ewing

“I really enjoy this time of year... it slows down, it gives you more time to carry on conversations with your customers,” she said.

Ms. Ignacio plans to keep her business open one more weekend in order to catch Thanksgiving holiday traffic.

“It’s a destination,” she said. “And people come up here for it.”

Ms. Ignacio said new businesses like Aquila choosing to extend the season at the Cliffs is inspiring, adding that Aquila and the Gay Head Store, a general store that closed for the season earlier this fall, are better winterized than most of the other shops. Still, she said the desire to stay open has made some shop owners think about what the historic site could look like during the off-season.

“The Cliffs are always here, so it’s great for people to just keep coming,” Ms. Ignacio said.

Mya O'Neill working on the decorations at Aquila. — Ray Ewing

Mr. Araujo said some other businesses at the Cliffs, including the Gay Head Store, have plans in the future to extend their seasons. He added that the Outermost Inn, still serving lunch and brunch, is another major draw for the town as the weather grows harsh.

“I wish there was more of that,” he said. Mr. Araujo sees the off-season in Aquinnah as untapped potential, waiting to be realized. In a recent social media post from Aquila, the store lists a handful of reasons to visit the area over the winter, including nearly-empty beaches and a chance to reflect and energize amidst the abundant natural beauty.

“For me, it’s about setting the precedent,” he said.