Chippenhook had at least two schools and possibly a 3rd.
Per Bette (Ewing) Fox on May 5, 2020:
I believe that the Chippenhook School has possibly had three different buildings or two buildings with the second being enlarged and structurally improved. The first school was not a town school but was privately owned by three families then owned by two families by 1805. The assumption of ownership by three families originally would explain that ownership was in thirds and would explain why Lewis Walker ends up owning 2/3. I am basing my belief on the following events.
(1) Circa 1786 David Stoel purchased for $366 from Joshua Priest one acre at the northwest corner of the roads as well as one-half of the grist mill in the northeast corner of the roads. Stoel remained there until March 1805 when he deeded the same to John Hills. The sale also included Stoel's 1/3 right in the schoolhouse near the property and a pew in the Meeting House. In March 1806 the schoolhouse, which was 2/3 owned by Lewis Walker, burned down as the result of hot ashes left in a box. "Sat. 22 Mar. 1806 - Rutland Weekly Herald: Clarendon schoolhouse in west part of Clarendon was burnt with large number of books on 16 March 1806."
(2) 27 July 1808 it was voted to build a schoolhouse in the corner where the road that comes from Lewis Walker's intersects with the road leading to the mill (1869 map).
(3) Architectural Historian Curtis B. Johnson dates the "now" schoolhouse circa 1880. However it may have been constructed in 1876 when my G Grandfather Charles Ewing notes in his diary on the 21 and 22 November that he has been working at the schoolhouse putting in windows, etc. Was he working on a new building or improving the old? this schoolhouse has been moved across the road.
That 1880 dating is not firm however. Per Dawn Hance who worked with Mr. Johnson on this project, unless she provided him with specific research that dated certain structures, Curtis Johnson's dating was based solely on his interpretation of the architecture.
If the current schoolhouse was built in 1876, there have not been any photos surface to date of a predecessor structure. See the District No. 1 School, Quarterline Road entry in this collection for more photos and information on this school. Also the Chippenhook School State Historic Register entry.