Nestled in the sheltered waters of Casco Bay, just a short ferry ride from Portland’s bustling Old Port, Cushing Island offers a rare blend of natural beauty, deep-rooted history, and a tight-knit island community. For over a century, this private enclave has been a beloved retreat for generations of families, each summer ferrying stories and traditions across the waves, keeping the island’s heritage alive.
The Island’s Earliest Days
Cushing Island’s history vastly predates its modern-day summer cottages and meandering dirt lanes. Before European settlers arrived, the island was frequented by the Wabanaki tribes, who hunted, fished, and navigated the surrounding waters for thousands of years. The island’s earliest documented European history begins in the 1600s, a testament to the area’s strategic and scenic significance.
Namesake and Early Settlement
The name “Cushing Island” pays homage to Lemuel Cushing, a prominent Bostonian businessman. In the 1850s, Lemuel and his family purchased much of the island, beginning its transformation into a summer haven. Before that, the island had cycled through a string of names — “Bang’s Island” and “Fort Island,” reflecting its historic fortifications and various private owners.
The Cushing family’s imprint is unmistakable. Throughout the next several decades, the Cushing family oversaw much of the island’s development, constructing roads, establishing rules for land use, and ensuring the island maintained its charm and tranquility.
Fort Levett: Defending Casco Bay
One of the island’s most fascinating historical milestones is the creation of Fort Levett. Built in the 1890s as part of Portland Harbor’s coastal defense network, the fort remains a striking reminder of the days when the U.S. Army guarded these rocky shores against potential threats.
The fort, named after Captain Christopher Levett, an early English explorer and settler of nearby Portland, was equipped with sprawling batteries, gun emplacements, and barracks. While the fort never saw direct conflict, its presence marked Cushing Island as an important cog in the nation’s defenses during both World Wars. Today, Fort Levett’s remnants — crumbling concrete bunkers and hidden artillery positions overlooking Whitehead Passage — serve as evocative landmarks, enticing adventurous islanders and history buffs alike.
Victorian Grandeur: The Ottawa House
At the turn of the 20th century, Cushing Island grew in popularity as a summer destination for Portland’s (and Boston’s) well-to-do. The centerpiece was the grand Ottawa House hotel, built in 1888 atop Ottawan Point. The hotel, in its heyday, boasted sweeping verandas, ballroom dances, and breathtaking views of the Atlantic. It drew artists, writers, and families seeking sea breezes far from city life.
Sadly, the Ottawa House burned down in 1917, but its legacy endures as one of the most fondly remembered landmarks in the island’s history. Today, its site is marked by gentle clearings and spectacular water views — a favorite picnic spot for islanders.
Community, Cottages, and a Unique Way of Life
What truly endears Cushing Island to its families and visitors is its sense of community and constancy. Unlike some seasonal colonies, Cushing Island remains steadfastly private, with no bridge or car access from the mainland. In the warm months, the island comes alive with laughter, cookouts, and games of tennis or croquet at the Cushing Island Club, situated centrally among the cottages lining Cushing Avenue and the Main Road.
- Cushing Avenue and Main Road serve as the island’s main arteries, lined with quaint shingled cottages, many dating back to the early 1900s. Some even bear the original names of their first owners or whimsical titles chosen by descendants.
- Lover’s Lane, a winding path leading past pine forests and open meadows, offers a peaceful stroll for those who want to experience echoes of the past.
- The historic Cushing Island Store, now a gathering spot and the only business on the island, reflects the community’s self-sufficiency and camaraderie.
Island Stewardship and Evolution
Cushing Island’s residents have long been stewards of the environment. Much of the land remains in its natural state, crisscrossed with trails that follow the bluff’s edge or cut through sun-dappled woods. The island’s beaches — Little Beach and Casino Beach among them — are cherished for swimming and searching for sea glass, but also protected by a shared commitment to conservation.
Though the island once thrummed with the energy of bustling hotels, military fortifications, and even a ferry landing at Whitehead, today it moves at a gentler rhythm. Cottages have been carefully preserved, and the Cushing Island Association ensures that the island remains family-friendly, car-free, and in tune with the natural world.
A Sense of Timelessness
Ask any longtime resident what makes Cushing Island special, and you’ll hear about stone-walled paths, moonlit ferry rides, and days that seem to linger — as if time itself slows down among the spruce and sea roses. Islanders recount generations learning to sail in the protected waters off Casino Beach, or gathering for Fourth of July festivities beneath the island’s iconic lighthouse-style beacon.
For all its storied past, Cushing Island endures as a living community. Each summer, families return to their cottages, children explore the beaches and woods, and old friends share porch-side stories as the sun sets over Portland Harbor. The traditions endure, growing richer with each passing season, anchored in a landscape that has weathered centuries of change but remains a beloved haven on the waters of Casco Bay.
Visiting Cushing Island
While the island remains primarily private, its visible history and legacy are very much part of Portland’s broader story. The ferry gliding past Cushing’s rocky headlands offers glimpses of the classic New England summer retreat — a place where yesterday and today gently intertwine.
Cushing Island’s history is not simply found in its remaining structures or scenic trails, but in the enduring spirit of community and stewardship that continues to define life here. In this special corner of Portland, the past is never far from the present, and the island’s legacy is preserved in every wave on the shore.