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Country Day was started in 1937 by a small group of Cedar Hill citizens to renew old friendships. In the beginning it was called the Old Settlers Reunion.
A few years later it came under the supervision of the Cedar Hill Volunteer Fire Dept.

As time went on, the event grew and many former citizens of the area returned home for a few short hours each year to renew their friendships. In later years it was taken over by the Chamber of Commerce and now is under the supervision of a group of concerned citizens known as The Friends of Country Day, Inc. In early 2000, Country Day on the Hill was incorporated in a need to reinforce the already strong structure of the nonprofit organization. It has grown in the last few years to crowds estimated between 8,000 and 10,000 visitors on the streets of our Historic Downtown Cedar Hill, Texas, and is an annual fall festival event of which Cedar Hill is very proud of. It is sponsored by the Country Day Committee, City of Cedar Hill, generous businesses and private citizens.

The annual fair is held on the second Saturday each October.