1886
Harold Kainalu Long Castle was born, the only child of James Bicknell Castle and Julia White.

1893
Kaneohe Ranch begins with Nannie H Rice leasing 15,000 acres to J.P. Mendonca and C. Bolte for cattle ranching.

1894
Kaneohe Ranch Company, Ltd. incorporated.

Early 1900s
Kaneohe Ranch lands are used for raising pineapple, processing sugar and cattle operations.

1905
James B. Castle acquired the interest of Mendonca and Bolte; negotiated a lease with Nannie Harris Rice of Boston, Massachusetts.

1907
James B. Castle purchases additional large blocks of shares in the Cattle operations which include some 7,000 acres of range land in Kailua. The properties come under the name Kaneohe Ranch Company, with the Castle Family at its helm.

1910
1,000 acres of Kaneohe Ranch land in Kaneohe are planted in pineapple.

1917
Harold K.L. Castle purchases the title to 9,500 acres in Kaneohe and Kailua from Nannie H Rice. The first parcels of Kaneohe Ranch land were made available for residential development.

1920
The census shows that 1,045 people live in the Kailua ahupua‘a.

1921
Lanikai is covered with melon farms and the only house is Mr. Castle’s cottage. The dirt foundation of the “Old Pali Road” is now paved.

1923
Planning begins for the Coconut Grove subdivision. Elsie’s Store, the site of the existing Kalapawai Market, opens for business. Lanikai Store, currently Kailua Beach Center, was across the street.

1924
The first real estate subdivisions were built at Lanikai (called Lanikai Crescent) with Kaneohe Ranch land accounting for approximately one half of total acreage. Mid-Pacific Country Club opens.

1940
Kaneohe Ranch Company moves its headquarters from the Spanish-style Castle home on old Pali Road to its current location at Castle Junction.

1948
The Lani-Kailua chapter of the Outdoor Circle is established in Kailua.

1949
Kailua’s 1st Fourth of July Parade is held.

Early 1950s
Kaneohe Ranch Company joined with Paul Trousdale and Hawaiian Housing Corporation for Windward housing projects, including developments in Aikahi, Kaimalino, Kalaheo, Mokapu, Olomana, Pikoiloa, Pohakupu and Yacht Club Hills. Population reaches 7,740.

1953
Harold K.L. Castle leases 221 acres at the base of the Pali lookout for the Pali Golf Course for $1 per year to maintain open space.

1954
The first traffic light in Kailua is installed at the intersection of Kuulei Road and Kailua Road. Foodland opens Windward Oahu’s first modern supermarket across from Kailua Beach Park.

1957
The Pali Highway and Tunnel is complete. Times Supermarket opens a new store in Kailua Shopping Center.

1960s
Subdivisions are developed in Keolu Hills, Olomana, Aikahi and Kainalu. Kailua’s population skyrockets to 25,622.

1962
Harold K.L. Castle donates 150 acres for the Hawaii Loa College campus, now known as Hawaii Pacific University.

1963
Castle Hospital opens on land donated by Harold K.L. Castle.

1965
The Kailua Drive-in Theater opens near Maunawili (currently Le Jardin Academy).

1967
Harold K.L. Castle dies at age 78, bequeathing a significant portion of his real estate assets to the Harold K.L. Castle Foundation which eventually becomes the largest private foundation based in Hawaii.

1974
Kailua celebrates its 50th anniversary since the founding of Kailua Town.

1976
Windward Passage, Kailua’s tallest building, is built.

1985
The Hamakua Drive extension is completed linking Kailua Town with Enchanted Lakes.

1996
The H-3 highway and tunnels are open.

2000
Renovation of the family owned Kaneohe Ranch Office, which was originally built in 1939.

2004
Completion of the community planning process and the draft Kailua Town Master Plan.

2006
Opening of the Kainalu Plaza on Kailua Road.