Alex Wilcox Cheek’s alarm went off a few minutes before 10 a.m. on a recent Sunday to reserve a parking space at a trailhead on the farthest tip of Martha’s Vineyard. The pressure, he said, was not unlike buying coveted concerted tickets.

He would later spend a morning among the trees — oaks, beetlebungs, maples — gnarled with time and salt spray from the Atlantic Ocean. He wondered, Had anyone ever seen these trees up close, in person?

It was a fair question. After generations of private ownership, more than 330 acres in Aquinnah, once owned by Jacqueline Kennedy Onassis and her daughter, Caroline Kennedy, opened to the public last year as the Squibnocket Pond Reservation, with a new trail added in July.

The property includes windswept moors, burbling creeks and an exclusive swimming beach. It not only offers a prime example of how one of history’s most famous families, back in the cultural discourse with shows like “Love Story” and a run at Congress, has enjoyed the privacy of natural beauty. But it also cracks open a corner of Martha’s Vineyard, so untouched, that other multimillion-dollar properties — and the affordable housing crisis created in their wake — don’t even seem to exist.

In 1978, Onassis purchased the property, known as Red Gate Farm, for $1.1 million. Kennedy and her husband, Edwin Schlossberg, sold the land in 2020 for $27 million to two of the largest land conservation groups on the island, the Martha’s Vineyard Land Bank and the Sheriff’s Meadow Foundation. (The property was once listed at $65 million.)

The reserve includes two separate holdings. The north entrance is a woodland walk, and the south entrance has multiple trails, including some that lead to a half-mile-long beach, and, new this summer, a trail that skirts along Squibnocket Pond. There, visitors can peer into an old hunting cabin where the former first lady once hosted lunches.

Next year, the land groups hope to make kayaks available to take onto the pond.

But getting there isn’t for the faint of heart. Parking spaces to access the south entrance are limited to 10 spots a day in the summer and require an online reservation. Cellphone service is sparse. Ticks are ever present. And it’s about a 25-minute walk down to the ocean.

“Our goal from the very outset was to sight the trailhead far away so that you had to walk to get there,” said James Lengyel, the executive director of the Land Bank. “And when you got there you would be rewarded by the remoteness and your ability to enjoy nature pretty much by yourself.”

Jackie’s sanctuary

In the late 1970s, Onassis told her children that “she had fallen in love with the rolling hills, wild dunes and silent ponds of Aquinnah,” Kennedy wrote in a letter to The Vineyard Gazette in 2019. “My mother believed that a North Atlantic summer was one of the most magical gifts in life.”

Red Gate Farm, named for the original gate that stood at the front of the property, “provided her with the sanctuary she needed and the freedom to be close to nature, her family, her friends and her books,” her daughter wrote. “It was a perfect expression of her romantic and adventurous spirit.”

Onassis was largely welcomed in town, both for her efforts in preserving the land and for keeping within the Vineyard way: biking to the Gay Head Lighthouse, paddling on her kayak, checking her lobster pots, grabbing ice cream with her grandchildren and keeping a low profile.

The bulk of the property’s sale took place in December 2020 for 304 acres for $27 million. A year later, the Land Bank bought an additional 32-acre lot from the family for $10 million. (Caroline Kennedy declined an interview for this story.)

The Kennedy-Schlossberg family kept the traditional Cape Cod-style house, guesthouse and surrounding 95 acres in the transaction. But if you’re hoping to get a glimpse of the Kennedy compound or run into Jack Schlossberg on the beach, you will be out of luck. The was preserve purposefully sited to maintain the family’s privacy.

Still, this land is steeped in Kennedy memories: John F. Kennedy Jr. could be seen windsurfing down on Squibnocket Pond in the 1990s, before he died in a plane crash not far from the family’s home. Tatiana Schlossberg, Caroline Kennedy’s daughter who died in January, was married at the family’s home in 2017. Many islanders can recall taking walks along the Atlantic beach, only to be turned around by an armed guard when the family was in residence.

The land and the lore

Living year-round in a community where the economy relies largely on summer visitors has always been a difficult dance, none more so than in the last decade as soaring housing prices have trickled down to every facet of island life. But long before the concept of vacationland or a summer White House ever emerged, this land was — and remains — inhabited by the Wampanoag Tribe of Gay Head (Aquinnah).

The Wampanoag have lived on the island, known as Noepe, for thousands of years, with a tribal community anchored in Aquinnah. The new reserve includes many sites like Black Brook and Witch Pond, which are rooted in Wampanoag mythology.

Tribal leaders said they were not contacted by the Kennedy-Schlossberg family ahead of the sale, and would have tried to find a way to bring the ancestral land back into their ownership or stewardship.

“Whether we purchase it or not, we should be considered,” Kevin Devine, the chairman of the tribe, said in an interview.

Tribal members do have special access rights to the land for sustenance purposes, including hunting and foraging.

In 2006, the Kennedy-Schlossberg family made a $100,000 donation to the town’s affordable housing committee as part of a new subdivision plan. For the Land Bank and Sheriff’s Meadow Foundation, that donation satisfied consideration of any further affordable housing needs on the property.

“When you look at the coast from Boston down to Washington, there’s very little that is natural,” Lengyel said. “So when you have an opportunity to protect something natural within those poles, you don’t trifle it away. You’ve gotta pay attention.”

But Juli Vanderhoop, the chairman of Aquinnah Board of Selectmen and a tribal member, said the affordable housing crisis facing the island, one that has forced many local families to move off-island, was too critical to ignore. Vanderhoop said she would have liked to see some of the property include housing, and for the tribe to have stewarded the land, as a way to support people who call Aquinnah home.

“What’s the responsibility of the conservation society to give back to the communities that hold these special places?” she said. “Really, I mean, because we’re losing them.”

Vanderhoop, who also owns Orange Peel Bakery in town, knows the magic of this corner of the island well.

There are more than 30 rare species on the property, including spotted turtles, orchids and shorebirds. Adam Moore, the president of the Sheriff’s Meadow Foundation, admired one of the oak trees on a recent morning, and noted the different trunks sprouting from the stump.

“That’s one tree that was probably cut at one time,” he said. “That’s why it has one, two, three — no four — major trunks.”

Moore continued beyond the sea lavender and patches of poison ivy, crossing over raised boardwalks that zigzagged across windswept dunes. The ocean was at first a sliver on the horizon, and then unfurled without another person in sight.

Be careful of getting lost in the beauty on the boardwalks, he cautioned. “I’ve almost fallen off this because I start looking out,” he said.

A seal bobbed its head up to say hello, as terns skated across the water’s edge. The state of the beach is in the hands of the tides — sometimes it’s sandy, sometimes it’s rocky. But one thing is for sure, Moore said, “It’s a knockout beautiful beach.”