Beyond the Pines: Cherry Grove’s Renaissance as a Year-Round Queer Haven

Few destinations in North America carry the legacy and vibrancy of Cherry Grove, a hamlet on Fire Island off the southern coast of Long Island, New York. For decades, Cherry Grove and its neighbor, Fire Island Pines, have been synonymous with queer freedom, creativity, and community. While summer still brings throngs of LGBTQ+ revelers to its beaches and boardwalks, 2025 has marked a noticeable shift: Cherry Grove is becoming a year-round destination, drawing a diverse spectrum of queer travelers well beyond the high season. Recent developments in community events, expanded off-season offerings, and renewed investment by LGBTQ+ entrepreneurs are reshaping the Grove’s appeal to those seeking an authentic, affirming experience—without the summer crowds .

Cherry Grove’s historical significance in queer culture is profound. Since the early 20th century, it has provided a rare refuge where LGBTQ+ people could express themselves openly—decades before such freedom was possible in most American cities . The Grove’s legacy includes welcoming transgender people, lesbians, gay men, bisexual, and non-binary visitors, fostering a culture of acceptance that endures today. The area’s architectural quirks—mid-century cottages, wild gardens, and wooden boardwalks—speak to a community built by and for LGBTQ+ people.

In 2025, local organizations have undertaken new efforts to honor this history. The Cherry Grove Archives Collection, for example, recently digitized decades of photographs and oral histories, making them accessible to visitors and researchers alike . Guided walking tours, offered on select weekends, showcase sites pivotal to LGBTQ+ rights and artistic expression—an initiative praised by The Advocate for its intergenerational bridge-building .

While Cherry Grove’s summer traditions—like the Invasion of the Pines and high-energy drag shows at the Ice Palace—remain legendary, the community has recently expanded its calendar to attract off-season travelers. In fall and winter 2025, Cherry Grove has introduced a series of queer-led wellness retreats, artist residencies, and community potlucks. The revitalization of the Cherry Grove Community House, a National Register landmark, has enabled year-round performances, including queer theater, music, and storytelling nights .

Local restaurants and bars, like Island Breeze and the Blue Whale, now remain open on weekends through much of the shoulder season, offering cozy spaces for connection. LGBTQ+-owned guesthouses have adapted with off-season rates and extended stays, appealing to remote workers and creatives desiring a communal, affirming environment .

Cherry Grove’s transformation is guided by a renewed commitment to intersectionality. In 2025, local organizers have launched events centering trans, non-binary, and BIPOC voices, including film screenings and panel discussions addressing the intersections of race, gender, and sexuality within queer spaces . The Grove’s longstanding tradition of drag performance now embraces a broader spectrum of gender expression and artistry, reflecting the evolving landscape of LGBTQ+ culture.

Community leaders have also prioritized accessibility, with boardwalk improvements and partnerships with disability advocacy groups ensuring that Cherry Grove remains welcoming to all. Mental health workshops and support groups, organized in partnership with New York City-based LGBTQ+ organizations, provide vital resources for both residents and travelers, addressing the unique challenges faced by queer people in retreat-like spaces .

Reaching Cherry Grove requires a sense of adventure: visitors board a train or drive to Sayville, then take a ferry across the bay. The absence of cars on the island evokes an immediate sense of escape. In recent years, local environmental groups, many led by LGBTQ+ activists, have promoted sustainable travel practices—encouraging visitors to minimize waste, respect fragile dune ecosystems, and support local conservation initiatives .

Seasoned travelers recommend visiting in late September or October, when the Atlantic is still swimmable and the island’s natural beauty is at its peak. Off-season, the pace slows, and the sense of queer community deepens, with intimate gatherings replacing the spectacle of peak summer parties.

In a travel landscape where many LGBTQ+-friendly destinations have become heavily commercialized, Cherry Grove offers something rare: authenticity rooted in lived experience, intergenerational community, and ongoing activism. As queer travelers seek destinations that are both fun and meaningful, Cherry Grove’s renaissance stands out. Whether participating in a storytelling night at the Community House, hiking through the Sunken Forest, or sharing a meal in an LGBTQ+-owned cafe, visitors to Cherry Grove find a space where joy, resistance, and belonging intertwine.

In 2025, Cherry Grove is not just a summer escape, but an evolving queer haven—one that honors its past while welcoming the full spectrum of LGBTQ+ identities into its future .