[2] Cherry Grove, along with nearby Fire Island Pines, is considered one of the most popular lesbian, gay, bisexual, and transgender (LGBT)–accepting resort communities in the United States.

[4] In 1921, the Perkinson family sold all the land east of Duryea Walk to Lone Hill, and then divided what was left into 109 building lots.

In their stead, the gay community that already frequented the island settled there moving from Ocean Beach, with figures such as Antoine de Paris and W. H. Auden leading the way.

[5] In the 1950s, Cherry Grove was already known as a "safe haven" one of three that included Provincetown, Massachusetts, and Key West, where they "could only fleetingly enjoy a carefree, 24-hour-a-day queer life by running off to a handful of destinations comfortably removed from a homophobic America.

[6] The gay aura of the town supposedly arose when Christopher Isherwood and W. H. Auden arrived dressed as Dionysus and Ganymede, carried aloft on a gilded litter by a group of singing followers.

[7] Truman Capote stayed at the Carrington House, just east of Cherry Grove, where in 1957, he completed his groundbreaking novella, Breakfast at Tiffany's.

While the Grove has its charms, several residents in 2005 expressed concerns about the lack of any services and population in the winter, the high cost of food and beverages, some "disrespectful visitors who come to party ... 'Day trippers'" (especially on the 4th of July), over-regulation of zoning by the town of Brookhaven, and a large population of voracious deer who eat up both beach grass and private gardens.

[2] A new generation of entertainers and socialites call Cherry Grove their summer home, including Hedda Lettuce, Michael Musto, Panzi, and Wanda Sykes and her wife and children.

The entire community has a single seasonal post office, on Bayview Walk near the main dock, open from about May 1 to October 12, which is a popular place to congregate.

The Community House, located near the intersection of Holly and Bayview Walks, provides a wide variety of public services to the Grove.

In 2013, the Cherry Grove Community House and Theatre was named to the National Register of Historic Places for "the enormous role it played in shaping what gradually evolved into America's First Gay and Lesbian Town.

Civic activities in the Grove include charity events and an Awards Night, during which votes are taken and titles bestowed upon residents and local businesses.

The Arts Project of Cherry Grove hosts a flea market, drag shows, and a gala dinner and dance in late September.

CGFD is a Basic Life Support First Response (BLSFR) agency, and as such has New York state certified emergency medical technicians that operate in conjunction with Cherry Grove EMS[25] and the Suffolk County Police Department's marine bureau officers, to mitigate medical emergencies and patient transport.

[16] Northwell Health operates two urgent care facilities on Fire Island (one in Cherry Grove and the other in nearby Ocean Beach).

If patients require medical treatment outside of those hours, the Immediate Care Center's physician can be reached on call by contacting local police.

In many cases, Long Island based ambulances will meet the boats once they cross the Bay (roughly 4.5 miles) and then drive individuals the short distance to one of the three hospitals.