Redding's story begins in 1714, when John Read became the area's first white settler, claiming 500 acres to establish Lonetown Manor as the center of a growing farm settlement. At the time, the land was already home to a Native American village led by Chickens Warrups. Read's son, Col. John Read, later took over the estate, and in 1767 the Connecticut General Assembly incorporated the town, then home to fewer than 1,000 residents, under the name Reading. The name was officially changed to Redding by the U.S. Postal Service in 1844.

Redding played a real role in the Revolutionary War. In 1777, British forces marched local roads on their way to raid Danbury, and the following winter, General Israel Putnam's division of Washington's army encamped in Redding, enduring conditions historians have compared to Valley Forge. That encampment is preserved today at Putnam Memorial State Park.

By the 1890s, Redding had become a retreat for city dwellers seeking quiet, among them the author Mark Twain, who purchased land in town and built his final home, Stormfield, in 1908. Twain lived there until his death in 1910, and his gift to the town, the Mark Twain Library, remains a cornerstone of Redding life today.