At the bottom of a hill sits land bank attendant Jody Sherman in a blue foldout chair, reading a book with a cooler by her side. Three young girls come by in their bathing suits, getting ready for a swim in Ice House Pond.

“I know these girls, they’re awfully cute,” Ms. Sherman said as they approach. “So ladies, just remember, we have lots of neighbors who are taking their afternoon naps, or drinking their bloody Marys on the porch. So be thoughtful as you swim,” she ends in a whisper with a finger over her lips.

A retired middle school teacher, Ms. Sherman is well trained in pleasantly telling people what they can and cannot do. Hailing from Richmond, Va., her southern drawl makes her instruction all the more gentle as she handles visitors coming to Manaquayak Preserve, better known as Ice House Pond, one of the land bank’s handful of properties with attendants at watch.

“I’m busy here. I have a lot of things to say to people coming by,” Ms. Sherman said. “I tell them to use the ladder off the dock and don’t go in the shallow parts because there is marine life with fragile habitats. We want to make sure the pond remains healthy, and that nothing is taken into the pond that would disturb its purity.”

Ice House pond is a kettle pond surrounded by tall woodlands, offering a quiet, serene visit. Ms. Sherman said plastic items such as snorkels and floats are toxic to the freshwater, and she has to ensure that guests understand the guidelines.

“It’s easier some days than it is other days,” she said. “But I meet a lot of awfully nice people. Some come often, and some are just tourists searching for an adventure.”

Five years ago Ms. Sherman came to the Island searching for an adventure herself, and has been coming back every summer since to work for the Martha’s Vineyard Land Bank, a public conservation organization created in 1986.

“My children grew up, graduated and moved away. When everybody left home, I wanted to reinvent myself. So that’s what I did. And I just loved it. I think a lot of people are that way. They come here searching for an adventure,” she said.

Back at the trailhead sits Bobby Howard, a 20-year-old attendant who has been coming to the Vineyard for vacation since he was born, from his hometown of Chelmsford.

“Here, you’re still in Massachusetts but it’s an escape,” he said. “This doesn’t feel like the real world. You almost forget that you have to follow the same rules as when you are on the mainland.”

This is Mr. Howard’s second year as a land bank attendant; he heard about the job from his older brother. Now he and three other childhood friends from Chelmsford are on the Island for the summer, all working for the land bank.

“They spread the word that this was an awesome job, and I like to think that we are good kids who work hard,” he said. “Pretty much everyone is respectful of the rules which makes my job better. I don’t like to be mean, but I don’t hesitate to enforce the rules. Most people understand that it’s a privilege that these properties are open to the public.”

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Aaron Jones at Great Rock Bight: “I sit around, read, draw on my shoes.” — Katie Ruppel

Having been to almost every land bank property, he said Chilmark Pond is his favorite spot, where he spends his time surfing on days off.

Mr. Howard attends the engineering campus at Penn State.

“I don’t get to see the ocean that much in Pennsylvania,” he said. “Growing up right by the ocean, it makes it hard not to see it. That’s why this job is awesome, I see the ocean everywhere I go.”

Up North Road and down a bumpy dirt road is Mr. Howard’s friend, coworker and roommate, Aaron Jones, who is drawing on his shoes, perking up when a car comes along to direct it where to park at Great Rock Bight.

“I sit around, read, draw on my shoes. I don’t know if you saw my truck over there, but it’s completely covered in designs similar to this,” he said pointing at his Rastafarian-colored shoes.

Waves and swirls of lines on his red truck create a funky maze.

“More so than anywhere else, people on the Island have given me compliments on my truck,” he said. Last week working at Moshup Beach, another land bank property, he built a rock sculpture that had everyone taking pictures.

“Some lady even made me a sign saying, Do not touch, artist at work.”

Artist at work, and attendant at work, too. In addition to keeping track of the number of cars and people coming into Great Rock Bight, he makes sure they stick to the rules of no dogs on the beach and no alcohol.

“Imagine a beach that you go to that’s supposed to be private — a back-of-the-woods kind of thing — and then there’s a bunch of dogs and people partying,” he said.

Working his way toward a degree in science, Mr. Jones has enjoyed learning about the different plants and uses of each property, and takes advantage of them, whether it’s through surfing, biking or hiking.

Although this is his first year as an attendant, he has been vacationing on the Island since he was a kid.

“I would stay in Oak Bluffs or Edgartown, but now I’m in the middle of the woods,” Mr. Jones said. “Now that I work for the land bank I like it here even better.”

Farther up-Island and down the Aquinnah Headlands Preserve trail, Moshup Beach is sprinkled with colorful umbrella tops housing bright bathing suits and beach toys.

Land bank attendant Leif Hopkins sits in a low-lying beach chair, his long hair in a ponytail, sunglasses on.

He goes to the shore and collects a few tiny crustaceans, bringing them back over on his fingertips.

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Leif Hopkins at Moshup Beach: “I see properties change throughout the years.” — Katie Ruppel

“This is the talk of the day,” he said of the shrimp-like amphipods. “A lot of kids were complaining, it looked like they had mosquito bites. But I don’t think they bite, they just have sharp microscopic hairs.”

Mr. Hopkins has been working with the land bank for 12 years, living everywhere from Malasia to Ecuador in the off-season. He is now a high school teacher at the International School of Aruba, instructing a number of classes including marine biology and forensic science.

In addition to being a land bank attendant, Mr. Hopkins takes water samples and checks on sea birds during the summer. Just last week he paddled out to a piping plover nest at the Tisbury Great Pond, where chicks were freshly hatched.

At Moshup Beach, he said he keeps an eye out for people carrying away clay from the Gay Head cliffs and also starting beach fires, and in general he tries to be a point of contact for people to ask questions about the property.

“I get to chill on the beach, and I see the properties change throughout the years,” he said.

“I like the idea of getting to be a steward for my environment — I have a lot of respect for it. It’s always been a place I’ve come home to.”