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For the first 15 years of its operation, Wildwood tried mainly controversial learning styles, such as dropping phonics from its curriculum. In the late 1980s, Hope Boyd formerly the headmistress of Westlake School for Girls, became the head of Wildwood. She began to stablize Wildwood's academic course. In 2000, Wildwood opened a secondary school, which started off with only 100 students. George Wood, a respected national educator and principal of Federal Hocking High School in Ohio, was the founding director of the secondary school.
At the elementary school, Wildwood incorporates multi-age primary classes. They are known as the Pods. There are six pods, and each pod contains children from grades K-2 mixed together in small class size. The reasoning behind this is that the older children can influence and lead the younger children, starting at a very young age. The elementary school also encourages parent participation and every week during "all school meetings", parents are invited to be updated on school news and events.
At the secondary school, no traditional grades are given, and instead teachers grade the students through The Seven Habits of Heart and Mind. The Seven Habits of Heart and Mind come from a national organization known as the Coalition of Essential Schools and focuses more on the student as a person. Instead of report cards , the students also receive narrative assessments . Narrative assessments are comprehensive reports written by the teacher specific to each of the The Seven Habits of Heart and Mind. Rather than daily assignments, lectures, and "busy work", the students at Wildwood School receive long term projects with flexible guidelines. This creates an environment of self directed learning with teacher guidance available when necessary. The secondary school encourages a system known as advisory , where specific age groups are mixed and kept in the same advisory group and teacher for two years. Advisory is group of 12-14 students with one advisory teacher. In Advisory, the students learn to bond with each other, participate in seminars and discussions, and have a theraputic place to vent or discuss. The advisor is responsible for the students in his or her advisory and frequently checks in with them on their progress academically and socially. The different age groups mixed in advisories are 7th and 8th, 9th and 10th, and 11th and 12th. Class sizes remain small and students are encouraged to learn independently, collaborate with other human beings, and to always seek evidence when presenting arguments.
Wildwood discourages a competitive learning environment and does not give out midterms or finals . Rather, Wildwood students demonstrate their learning through 50 minute presentations known as gateways at the end of 8th, 10th, and 12th grade. In all grades, parent teacher conferences are held three times a year with the student's advisor.
Wildwood strongly encourages its students and faculty to reach out to the community around them. As a result, part of the curriculum of Wildwood includes going out and helping the less fortunate in the community. This ranges from participating in senior citizen centers, homeless service centers, elementary schools, and various other community service sites. Students are required to participate in these activities during school hours for 3 hours a week. In 2001, the Bill and Melinda Gates Foundation granted Wildwood with the funds to create an Outreach center. As a result, Wildwood has been exporting its progressive philosophy to a number of public schools in the region.