1925 – On October 7, 1925 a parade with some 4,000 people including 3,000 children marched from downtown to the Park. Julia Riley, the sister of James, still lived in the family home and acted as hostess giving tours of the home. After the parade the children from each school in the county planted a tree in the park.
1930 – Riley Park swimming pool dedicated, July 4th.
1937 – Elaborate plans were made for Riley’s birthday. Dedication of the Riley Park Shelter house was held during his birthday celebration Guests included the Gov. of Indiana and important people from all over the state as well as Mr. Riley’s nephew and nieces.
1941-1944 – Sometime between 1941 and 1944 the SS James Whitcomb Riley was built by the Oregon Shipbuilding Corporation in Portland Oregon. Her hull number was 193. She was one of many ships built and named after famous American Poets. The RILEY was built for the War Shipping Administration Transport and the ship was charted or operated by the Army Transportation Service. The ship was built to hold 550 troops, wartime cargo and fighter aircraft on the decks. It was used to carry German POW ‘s in 1945. On May 11, 1944, the RILEY earned a Battle Star while operating in Convoy # UGS-40 it was attached by a German sub.
1949 – Arthur Downing, president of the Riley Old Home Society, had a dream to celebrate the 100th Birthday of James Whitcomb Riley. He saw a tower 77 feet tall covered with flowers. On September 30, 1949, Carl Droeger a local construction contractor and his crew built the structure which was covered with 4,800 square feet of wire mesh. The Tower of Flowers was the highlight of the Riley Celebration that year. Gov. Henry Schricker and his wife visited Greenfield and he issued a proclamation that declared Oct. 7, 1949 as Riley Day throughout Indiana. More than 3,200 bouquets of flowers were placed on the tower. This same day the cornerstone was laid for a new research laboratory at Riley Hospital for Children.
1957 – The Greenfield merchants staged elaborate Frontiers Days. The Parade of Flowers, as we know it today was started. The parade was led by the Greenfield High School band. In later years the middle schools combined bands. In the early days the downtown merchants staged what was known as Frontier Days when old fashioned costumes were worn. Bunting was placed on every building downtown. The celebration was also known as Sidewalk Days and the Riley Days.
1964 – The Riley Days was a two day event that included the Flower Parade, Riley Wranglers, a free show at the Weil Theater for children and Sidewalk booth sales by the area merchants. The event was co-chaired by Dale Beagle and Dick Robertson.
1965 – This year saw a three day event with the Parade of Flowers being on Thursday. Robert Eagleston was Chairman.
1966 – The Riley Days was again a two day event and featured Lucky Numbers, a German Band, the Greenfield Majorettes and Rinky Tink Piano Player. Many civic groups set-up stands for the sidewalk sales.
1967 – The 118th anniversary of the birth of James Whitcomb Riley was celebrated. Twenty-one organizations had booths, the American Legion held a fish fry, and a band concert was held on Friday night, and the downtown merchants made plans for special sales for the event.