Whitman was first settled by Europeans in 1670 and was officially incorporated in 1875. Prior to becoming Whitman, it was formally the southern parish of the town of Abington. The new name, Whitman, was taken from Augustus Whitman, whose family who grew up in South Abington, and was adopted in 1886. Though before adopting the name Whitman, the small town was known as Little Comfort.
Whitman has a rich history that is deeply rooted in the shoemaking industry. Regal Shoe and Bostonian Shoe are perhaps the most notable. At one time there were over 20 shoe factories and related factories making metal shanks in town. There are a few abandoned factories left, and some have been turned into condominiums.
In the late 1930s, Ruth Graves Wakefield invented chocolate chip cookies in Whitman at the Toll House Inn on Bedford Street. The Toll House burned completely on New Year's Eve 1984, in a fire that originated in the kitchen. The inn was not rebuilt. The site is marked with a historical marker, and that land is now home to a Wendy's restaurant and Walgreens pharmacy, with the Toll House sign still in existence. The former Whitman Savings Bank was also the first in the country to offer savings bank life insurance (SBLI). Whitman is the home of the famous Peaceful Meadows Ice Cream, as well as the former home of Saftler's Inc., one of the oldest and largest independently owned fabric stores in the country, which closed in June 2011. In 1964 The Venus Cafe was founded by former professional wrestler Peter Drosos, who fought under the name Pete "The Golden Greek".
From 1968 to 1994, Whitman was also home to King's Castle Land, a children's amusement park owned by the Whitney family and located near the intersection of Routes 18 and 14.