Stump Grinding in Middle Island

The European-American history of Middle Island goes back at least to 1766, when the first Presbyterian church was built. Rev. David Rose, who was also a doctor and a pastor of the South Haven church, covered his immense parish on horseback. He filled his saddle bags with Bibles and medicines to minister to his frontier congregation. In 1766 the parish opened a cemetery just across from the church.

Around the same time, a veteran of the French and Indian War named Jonathan Edwards who admired the white pine trees of Quebec swiped the seedlings for himself and began planting them along what is today Middle Island-Miller Place Road. Many of these pine trees were spread throughout the community. A local farmer named William Dayton swiped some of the pine cones from the site of the original plantings in 1812 and brought them to his farm south of what is today Middle Country Road, towards an area of Yaphank-Middle Island Road north of Longwood Road. The area near the William Davis farmstead is now part of Prosser Pines and Cathedral Pines County Parks.

The first schoolhouse was built in 1813 east of the church. In 1837, a new church was built just to the rear of the older one. It served the community for 200 years until the new Christian Education building was built at the Longwood Estate in 1966.