When January hits, the Simon family starts thinking about going north — north as in Massachusetts — in August.

Many people book their homes the day they turn in their keys at the end of summer. This year, the Simon family lucked out and secured their favorite rental: a two-level, 4,000-square-feet, six-bedroom home in Edgartown, Martha’s Vineyard’s first Colonial settlement. And just in time for the annual African-American film festival.

Martha’s Vineyard, the go-to summer destination for the Black elite, offers an escape from the fast-paced concrete realities of urban living to recharge, network, and even strategize to elect political leaders — possibly the country’s next Black president.

Picture a family-focused version of MACo in Ocean City or Las Vegas for ICSC — but even more exclusive and storied.

Bravo’s “Summer House: Martha’s Vineyard,” a new Black Oak Bluffs-inspired collection by Ralph Lauren, and that gorgeous episode 5 of “Forever” on Netflix have drawn renewed attention to the retreat, an oasis for parents.

“It feels like a Black utopia to me. It’s just a happy place,” said Kuren Morgan, who doesn’t think twice about letting her now-teenage twins go out by themselves to play until dusk — something she would not do in Baltimore. “I can go porch hopping. It feels like a big fun summer camp.”

Chris Simon first visited in 2022, a “Wakanda” moment in which the 42-year-old was struck by the mix of “likeminded individuals” who came for a good time while networking and exchanging opportunities for future “synergy” back in Maryland.

On subsequent visits, Simon, head of BTST Services and BLK Swan, the first Black-owned restaurant and bar in Harbor East, was a guest of the luxury fashion brand Balmain, where he mingled with the likes of Tina Knowles.

Simon’s wife, Janeen Simon, who did not visit that first year, took a little more convincing about Martha’s magic.

“I didn’t pay him much more attention,” recalled the 39-year-old co-owner of BLK Swan and Self.ish Beauty Spa in Pikesville. “Then, I started meeting more people who went. I got excited. It was honestly a really good time. Now we go every year.”

This August, Lillian Sparks Robinson, 49, a Gwyn Oak resident, her husband, Corey, and their 10-year-old son, Connor, plan to return to the Vineyard, where she’s been summering since 2011.

“The people make the island so special,” Robinson said. “If you go to the island, not knowing anybody and looking for some sort of turned up time, it probably won’t have the same appeal, but if you’re going there looking to connect with the people you’ve been connecting with year after year, then you’re gonna have the best time and make the best memories.”

Karen Miller affectionately calls the island “The Mecca” for Black political fundraising.

“Donors are expected to and expect to pay a premium to attend fundraisers at Martha’s Vineyard,” Miller said, likening those fundraisers to “Jim Clyburn’s World Famous Fish Fry” in South Carolina.

A 2022 fundraiser for then-gubernatorial candidate Wes Moore was an early sign of the rainmaking ability he has demonstrated for fellow Democrats, the Democratic Governors Association and his own campaign. The event featured tickets costing up to $6,000, and attracted those hopeful to hitch themselves to Moore’s growing national profile.

Sen. Angela Alsobrooks swooped in last August and held a fundraiser as she picked up steam in her historic win as Maryland’s first Black female U.S. senator.

“There are not many places where you get that many of us on that level to get together, figure life out and share resources,” said Chris Simon, who attended last year’s Moore fundraiser at Oscar-winning filmmaker Spike Lee’s property in Oak Bluffs. “Spike Lee opened up his home — his personal residence in Martha’s Vineyard. He ‘s not doing that in New York, but he feels comfortable in that environment.”

Once a stop on the Underground Railroad, then known as a favorite destination for famous figures of the Harlem Renaissance, it eventually offered a reprieve for Black people from areas that didn’t allow them to use public beaches and other entertainment attractions.

It continued to attract the likes of the late Maya Angelou, who was a regular. So was the Rev. Martin Luther King Jr., who stayed at the Overton House in Oak Bluffs. You might even catch a glimpse of media mogul Oprah, who is often spotted taking walks throughout the small sleepy island peppered with a mix of quaint Victorian cottages in technicolored grandness and HGTV-worthy palatial dwellings.

HBCUs and Divine Nine organizations have a strong presence on the vineyard with a series of receptions and other activities.

Morgan State University has gone so far as to dedicate a week in August to networking and fundraising on the island.

Greg Jones, a 1979 alum of Morgan State, started the week from the backyard of his Vineyard home. That initial gathering has grown to a bigger venue offering a week’s worth of events that include a state of the university speech by President David K. Wilson.

Another lure — especially for parents — is the safety and peace of mind the island brings.

Janeen Simon, a member of Jack & Jill of America Inc., loves that Black youths can “just be kids” there — something other mothers echoed.

The growing popularity of the Vineyard has had an adverse affect on regulars who return each year, however.

Some fear the end of serene moments of capturing the breathtaking sunsets along the cliffs of Menemsha Public Beach, or the ability to snag fresh apple fritters at Back Door Donuts in Oak Bluffs, or even to partake in the daily Polar Bear Club morning swims and yoga sessions along Inkwell Beach.

Data shows that Marylanders flock there seasonally. They own 231 homes on the Vineyard, which means Maryland has the 8th-highest number of residents owning homes on the Vineyard, according to Martha’s Vineyard Commission’s Seasonal Population Estimate for 2024. Those numbers do not reflect the additional throngs who rent houses there for weeks at a time.

Prices and availability for homes in August, which includes Morgan’s events, the film festival and Illumination Night, where Japanese lanterns decorate the rows of “gingerbread cottages” throughout Oak Bluffs, come at a premium.

According to the Associated Press, a recent housing report by the Martha’s Vineyard Commission found that the average nightly rental rate among more than 3,000 short-term properties is $931, and that the average home price more than doubled to $2.3 million over the past 11 years.

Kuren Morgan, for one, still wants people to come to the Vineyard.

“Just come in May, or June,” she laughed.