From before 1896 until 1951, the Woolford School operated next to the Milton Methodist Church. A center of the Woolford community and village life, the school had one classroom for all six grades and a small storage room in the rear. The school was heated by a potbellied wood stove. On cold mornings, the desks were arranged in a circle around the stove until it warmed the room. The unheated rear room held books, pupil’s coats, a few games, paper, chalk and supplies for the PTA plays. Water was hand pumped to a bucket with a dipper and the boys and girls had separate outhouses. The old school building is gone now, replaced by an addition to the church.

A school photograph for 1897-98 records Maud Newbury, Lee Brooks, Ethel Asplen, Colie Newbury, Lola Woolford, Lily Landers, Reese Williams, Raymond Williams, Charles Brooks, Maurice Dunnock, Leon Woolford, Purnel Williams, Gertie Travers, Rudolph Landers, Ben Landers, Liddie Brannock, Emma Dunnock, Goldie Asplen, Olivico Foxwell, Hattie Parker, Bertha Brooks, Miriam Williams, Myrtle Linthicum, Blanch Newbury, Maggie Landers, Nellie Asplen, Bulah Brooks, Paul Dunnock, Willie Mills, Ella Moore, and Gay Richardson. The names remind us of families here then and today.

Times changed and in the early 1950s, the school was closed and the property was sold to Milton Church. A Social Hall was built on the new site. The old school had a flagpole and when the building was razed, the pole was moved to the nearby home of Mr. and Mrs. Phillip J. Higgins. In time that family moved to Cambridge but wanted the flagpole to stay in Woolford. It went to the Woolford home of Fred and Nancy Collins family and there remained.

Over the summer of 2005, the Milton United Methodist Church asked its members if anyone had a suitable flagpole as plans were made to have a flag and flagpole outside the Church. Nancy Collins immediately offered the former school pole. Nancy had been a student at the Woolford School and now is on the church council of Milton Church.

A community effort began with the gift of the pole by the Higgins and Collins family.

Donations and contributed services included a complete fiber glassed weather coating by Dennis Elzey of Elzey Boat Builders. A new gold ball at the top of the pole was fabricated by James Marshall and new hardware fitted. The pole was installed at the Church site by Fred Collins with a plaque to identify its history provided by Nancy and Fred Collins. A slate slab to display the plaque was donated by Ken Kloostra and Andie McCullars. Meanwhile, Lynne Schulman requested and obtained an American flag which had been flown over the US Capitol with a certificate stating “flown over the US Capitol for the Milton Methodist Church”. Electrical work and lighting for proper 24 hour display of the flag were donated by F L Travers & Son Electric. 

One of the special events of Homeconing Day  2005  was the re-dedication of the Woolford School flagpole with its new US flag. The Homecoming speaker was the Rev. Kevin English, Pastor of Zion United Methodist Church in Cambridge. The Rev. English accepted his first pastorate, with the Church Creek Charge, while a student. Following 11 years as Pastor of Centenary United Methodist Church in Laurel, he became Pastor of Zion. This year's music was a tribute to Earl Asplen who was a lifetime member of Milton church who died this year at the age of 101. The musical presentations featured soloist Lauren Shockley from Woolford and The Humble Beginnings from Cambridge with Janet Asplen, Kevin Asplen, Bob Fehsenfeld, Chuck Wheatley, Junior Vannoy, and Sam Oliver.