Woodstock's first public high school opened January 16, 1854. This opening was less than a year after the town, at its annual meeting, had voted to build the school. The land, purchased in April 1853, was on a knoll below Linden Hill. The current high school, built in 1957, sits on approximately of land along the
Ottauquechee River just west of the village of
West Woodstock on
U.S. Route 4. In 2023 school and community members proposed that a new school building be built. On 2026 Town Meeting day, 61% of voters approved a $112 million bond issue to support the building of a new school. Woodstock Union High School is consistently recognized for its educational quality and in 2020 was listed by
U.S. News & World Report as the third best school in the state. In 2025, Woodstock Union Middle School was named a "School of Distinction" by the
Association for Middle Level Education. It was one of only 24 schools recognized nationwide "for their outstanding commitment to young adolescent education." 2025 graduates attended schools including Dartmouth, West Point, and Yale. Following the 2025 passage of Vermont Act 73, Mountain Views Board of Directors Chair Keri Bristow recommended that WUHS serve as a regional hub district. In a July 28, 2025 letter to community members, Bristow cited the school's strengths in offering AP courses as well as programming in the visual and performing arts, music, STEM, trade-career preparation, and CRAFT - Community and Climate Resilience through Agriculture, Forestry and Technology. == Academic programs ==