History
A Home with a Storied Past
Built in 1893 by Sarah Chipman, the widow of Captain Barnabas Chipman, this Queen Anne Victorian was originally named The Overlook for its panoramic views of the Atlantic Ocean, Cape Cod Bay, and Minister Pond. Though today’s mature trees and the nearby National Seashore Visitor Center have changed the landscape, the inn’s historic beauty and welcoming spirit remain unchanged.
The property’s history is deeply rooted in Cape Cod’s maritime heritage. Captain Chipman, a Wellfleet-born sea captain, spent his life navigating the East Coast as the captain of the J.V. Wellington, while Sarah’s family played a prominent role in Eastham’s early cranberry farming. Their home became a gathering place, where family, friends, and travelers could find warmth and hospitality by the Cape’s shores.
In 1908, Sarah’s daughter, Abbie Freeman Chipman, became the inn’s next caretaker. That same year, a historic barn from their previous home, "The Walton," was moved to the property—a structure that today serves as The Carriage House, continuing its long tradition of hosting guests.
A Legacy of Hospitality
The Overlook evolved into The Overlook Lodge in 1929, officially welcoming visitors to experience the charm of Cape Cod. Among its notable guests was the naturalist Henry Beston, who wrote the beloved book The Outermost House while staying here. Throughout the Great Depression, the inn provided work for young locals, solidifying its place in the Eastham community.
Over the years, The Overlook Lodge changed hands, each new steward carefully preserving and restoring its historic charm. The Aitchison family, who purchased the inn in 1983, led a major renovation and expansion in 1988, seamlessly adding four guest rooms, a dining room, a fireplaced living room, and a billiard room (now the library) while maintaining the home’s Victorian elegance.
With its renovations complete, the inn rebranded as The Inn at the Oaks in 2001, named for the majestic oak trees that had grown since their planting in 1912, when acorns were brought over from England via Africa.
The Next Chapter
- A Dream Fulfilled
In May 2024, the inn welcomed its newest caretakers: Bernie and MaryRose Lynch, college sweethearts from Boston who moved to Cape Cod in 1995 with the dream of one day owning a historic inn. That dream, years in the making, has now come to life at Cape Cod Inn at the Oaks.
Their passion for preserving history, creating unforgettable guest experiences, and honoring the inn’s legacy ensures that every guest who walks through these doors becomes a part of its story.
Relax like Henry Beston
Henry Beston, a renowned naturalist and author, is celebrated for his 1928 work, The Outermost House, which chronicles his solitary year on Cape Cod's outer beach. This influential book is credited with inspiring the establishment of the Cape Cod National Seashore. During his time writing, Beston frequently sought respite at what is now known as the Inn at the Oaks in Eastham, Massachusetts. At that time, the inn was called the Overlook Lodge, named for its scenic views of both the bay and the ocean. The innkeeper would ride out to the beach to bring Beston back to the lodge, providing him with a place to rest and rejuvenate from his dune shack retreats.
The Inn at the Oaks has a rich history dating back to its construction in 1870. In the 1920s, it operated as the Overlook Lodge under the management of the Kelley family, who offered year-round accommodations with "good home cooking" at rates of $5 per day or $25 per week. The lodge provided employment opportunities for local youth during the Great Depression. In 1937, following a foreclosure, the property changed ownership to the Hall family.
Today, the Inn at the Oaks honors its connection to Henry Beston by offering the Henry Beston Suite, a two-bedroom accommodation located on the second floor of the Main Inn. This suite pays homage to Beston's legacy, allowing guests to immerse themselves in the same environment that once inspired his writing.
The current innkeepers continue the tradition of hospitality, preserving the inn's historical charm while providing modern comforts. Their dedication ensures that the Inn at the Oaks remains a welcoming retreat for visitors seeking to experience the natural beauty and literary heritage of Cape Cod.
