Shortly after the turn of the century (early 1900s), the Outer Cape became and increasingly popular summer destination for vacationers. The season was short, but a demand for accommodations was reason enough for some residents to build small groups of simple cottages in their back yards to host tourists. Known as "cottage colonies", these groups of small structures were usually constructed in an eclectic manner, making use of old used wood planks, doors, windows and cedar shingles.
One of the first cottage colonies to be built on the outer Cape is known today as Cottage Grove. The land was purchased in 1925 by Henry Clark, a builder and local resident of Eastham. Clark began construction of a 3-bedroom, Craftsman-style house on the 3 acre lot that same year. The house was built to serve as a residence for himself and his new bride, Dorothy. Clark finished constructing the main house in 1928.
After finishing the main house, a law was passed in the Massachusetts state legislature that mandated the removal of all billboards from Route 6 along the length of the Cape. Clark was subsequently awarded the contract to remove the signs on the outer Cape. Like a true Cape Codder, he reused salvaged materials, including the old billboards, to start building cottages on the back of his property as a means for generating some additional income for his growing family. He proceeded to build one cottage per year, completing the ninth in 1940. The cottages were officially named Bide-A-Wee Cabins (Scottish for "stay a while").
During this time, Henry and Dorothy had three children. Although the Clark Family sold the property in the late 1950s, their children, Dick, Norma and John all still reside in the Eastham area. Dick followed his father into the building trade and now captains fishing charters out of Rock Harbor. Norma Clark Mead lives within the bounds of the National Seashore and runs a Bed & Breakfast near Nauset Lighthouse. John is the artist of the family, expressing his talents through woodworking, writing, and storytelling. John visits the property occasionally and recounts the tales of the many wonderful guests of Bide-A-Wee during a time when the life and landscape of Cape Cod were simply different. His memory and imagination have been an inspiration to bring such a feeling back to the property and to the experience of its visitors.
Shortly after the Clark family sold the property (renamed Windward Cottages in 1956), the cottage colony business began to shift. With the popularity of motels on the rise through the 50s and 60s, most colonies began to have difficulty competing for the summer guests. Throughout the 70s and 80s, hotels and motels continued to be the preferred venue for visitors. After several decades of sliding popularity, most cottage colonies were in desperate need of market redefinition and physical updating.
In January 2000, Chris Nagle and Greg Wolfe purchased Windward Cottages from the Kostas family, the third owner. Appreciating their historic value, simple construction, and "crooked" character, Chris and Greg challenged the popular suggestion to demolish the cottages and start anew. Instead, they shored up the structural elements, exposed much of the old wood, and concentrated on updating the infrastructure. With an eye on keeping the old feel of the cottages, they incorporated old doors, windows, fixtures, and hardware wherever possible. The property is currently owned and managed by The Cottage Grove Condominium Trust.
History is what gives Cottage Grove its essence. When sitting in a cottage or walking the grounds, it is easy to sense the 70 years of characters and memories that have made the property what it is today.