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The desire to create The Highlands, Inc began in 1907 with Charles D. Stimson, Albert S. Kerry, Edward I. Garrett, and A.B. Stewart trying to find land to build an 18-hole golf course as there was not enough land in Seattle proper to do so. After the golf course was built, now known as the Seattle Golf & Country Club, they used the extra, heavily wooded 380 acres to build The Highlands, Inc. Highlands members elected Charles Douglas Stimson as their first president to guide them into the future, and he presided over the community for 14 prosperous and foundational years. Influential families from across the nation came together to create this community based on cooperation and seclusion in nature including William E. & Bertha Boeing (Michigan) of The Boeing Company, Donald E. & Fay Frederick (Georgia) of Frederick & Nelson Department Store, Morris A. & Georgie Arnold (Missouri) Bank President, Frederick R. & Estelle Delbridge Green (New York) of Remington guns and New England textile manufacturing, and Charles D. & Harriett Overton Stimson of Stimson Lumber. 

In 1907, the famed Olmsted Brothers cut the ribbon on one of their most ambitious design projects to date - a community of homes meant to be as integrated with their natural woodland surroundings as they were with the community.  Homes would rest surrounded by trees and connected by a scenic road system. The Highlands, as it was called, was placed on a hill overlooking the Puget Sound, so that a homeowner could take in the beauty of the forest and the sound with a single glance.  It was to be a place, upon entrance, where the noise and bustle of the city became a distant memory. This respect for seclusion is balanced by cultivation of scenic views, which are realized in the form of carefully cut corridors in the tree line.  Properties with these corridors gain access to the stunning vistas of the Puget Sound and Olympic Mountains, which are also seen from points along the roads. Additionally, the Olmsted Brothers designed numerous estates and gardens for Highlands members throughout the community such as Edward I. Garret, Donald E. & Fay Frederick, Charles D. Stimson, Belfagio Garden for John H. Ballinger, and R. D. Merrill. This immaculately and thoughtfully built neighborhood creates space for community, deliberation, relaxation, and living life. 

The first 33 years of the Highlands, Inc were marked by the creation of tradition and community. A few Highlands members generously donated many amenities still used by members today including the Highlands School, Florence Henry Memorial Chapel, the playground, the tennis courts, and community pool. However, the Highlands’ smooth history was rocked by the US entrance to World War II. Member John E. Ryan headed an air raid precaution and first aid committee in case enemy combatants harmed the community. Prominent members of the US Armed Forces came to live in the community such as Lieutenant and Mrs. Cunningham and Lieutenant and Mrs. Boyce. Women in the Highlands had a significant impact on the greater Seattle area during the War. For example, women such as Estelle Delbridge Greene and Carol T. Isaacson Jr trained with the Red Cross to work at military or civilian hospitals and to handle mass feeding in the case of evacuation or disaster. Other women such as Martha Isaacson, Katherine Baillargeon, Dorthy Stimson Bullitt, Mary Ryan, and Ethel Bogle were members of the Sunset Club and supported the war effort. Even in difficult moments, Highlands members came together to support one another. This support is a trademark of the neighborhood and exemplified through the Highlands’ response to World War II. 

After World War Two, the Highlands went through an era of unprecedented growth and modernization. In 1968 alone, 14 new families joined the Highlands membership! The Florence Henry Memorial Chapel also experienced growth as they became affiliated with the Episcopal Diocese of Olympia and St. Dunstan’s Episcopal Church. This affiliation was immensely successful as the Chapel hosted over 200 families while the Sunday School practically burst with over 200 children participating. However, the Highlands still owned the chapel and held other events for Highlands members of all denominations. 

The Highlands arrived in the new millennium with valued traditions still in place, and a spirit of creativity. The generosity of Highlands members present in the early years of the community has continued to grow into the 21st century. A prime example of this is the thoughtful donation of a community park to the Highlands, creating miles of easily accessible private trails for the neighborhood to explore. Highlands traditions also remain, including the annual Highlands Picnic where the community comes together for a full day of summer fun, organized by the Picnic Committee. Events are put on for people of all ages including golf, tennis, and croquet tournaments, a fun run and walk, and an evening celebration with dancing, catered by exemplary local companies. The Florence Henry Memorial Chapel is used for the yearly Chapel Concert Series, and continues to hold weddings, funerals, and special events for Highlands members. Families present in the Highlands for generations have continued to welcome new families with open arms to create a community based on tradition, independence, conviviality, and seclusion in nature.