In 1640, the Siwanoy Tribe vacated and sold land to the New Haven Colony which originally consisted of 28 families. In 1667, according to old town records, Stephen Holmes, a blacksmith, was granted land by the town (which was then Stamford). Holmes further expanded the land in 1699. 

The Holmes Family is one of the oldest in Darien. The ownership of the land two generations after Holmes is unclear but it stayed within the Holmes Family. Records indicate that John Holmes Jr., a fifth generation family member, inherited 145 acres in Stamford, including the area that is now Woodland Park Nature Preserve in 1784. John Holmes Jr. was a farmer and the land included his residence, a barn, pastures for horses and cattle, fields of crops. The house stood at the corner of Middlesex Road and Holmes Avenue.

Town records show that the land was passed on through three more generations of Holmes men, all named John. 

In 1919 the land which was then approximately 64 acres was purchased in sections by Walter Edward Irving, founder of the Subway Grating Company. The land at the time was cleared for farming and grazing along with stone walls that criss-crossed the fields. Irving allowed the land to grow back to its natural state. The land was named Irving Woods. 

In 1959, the land for the Woodland Park Nature Preserve was purchased by the town of Darien from Irving with the intent of it remaining a nature preserve for the Darien Community.

In 1979, the "Friends of Woodland Park Nature Preserve" was established to maintain and improve the preserve.