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Orangeville/Castlewood Field Aerodrome (TC LID: CPV2) is located 3 nautical miles (5.6 km; 3.5 mi) northwest of Orangeville, Ontario Canada.

Orangeville District Secondary School is located at 22 Faulkner Street in Orangeville, Ontario, Canada, and is the oldest secondary school in the town. It was built in its current state after the old high school (originally built in 1884) burned down in 1948. Currently, grades 9 through 12 are housed at O.D.S.S. There are 1,500 students that attend this school. The principal is Patrick Hamilton and the vice principal is Steve Wynen. Famous graduates include WWE stars Adam Copeland and Jason Reso, better known as Edge and Christian, Alex and Chris van den Hoef of DVBBS, NBA player Ignas Brazdeikis and Degrassi: The Next Generation actor Ryan Cooley. ODSS also provides the academic instruction for the Athlete Institute, an elite basketball prep school, which has recently featured 2016 NBA draft first-round picks Jamal Murray and Thon Maker, with Maker coming directly out of high school. Film director Richard Boddington graduated from ODSS in 1986.

Orangeville (Canada 2016 Census 28,900) is a town in south-central Ontario, Canada, and the seat of Dufferin County.

Westside Secondary School is a public high school located in Orangeville, Ontario, Canada that opened on November 25, 1999. The current population is 800 students.

Dufferin—Caledon is a federal electoral district in Ontario, Canada, that has been represented in the House of Commons of Canada since 2004. It was created in 2003 from parts of Dufferin—Peel—Wellington—Grey riding. This riding gained a fraction of territory from Vaughan during the 2012 electoral redistribution. After David Tilson's resignation, in March 2019 the Dufferin—Caledon nomination for the Conservative Party in the 2019 election was won by Harzadan Singh Khattra, amid accusations within the party of vote tampering, membership reimbursement, and payments to foreign students to attend, despite their ineligibility within party rules.

Dufferin—Caledon is a provincial electoral district in southwestern Ontario, Canada. It was created for the 2007 provincial election. The entire riding was carved from Dufferin—Peel—Wellington—Grey, and includes all of Dufferin County plus the town of Caledon in Peel Region. The riding also existed from 1987 until 1999 with the same borders, but was known as Dufferin—Peel.

Laurel/Whittington Aerodrome (TC LID: CLW3) is located 2 nautical miles (3.7 km; 2.3 mi) northeast of Laurel, Ontario, Canada.

Caledon Lake is a lake in Caledon, Peel Region, Ontario, Canada. Caledon Lake is within the Greater Toronto Area Greenbelt.

Salem is a Dispersed Rural Community and unincorporated place in the municipality of Mono, Dufferin County in southwestern Ontario, Canada. The community is located at the intersection of 2nd Line EHS and Sideroad 5, 5.3 kilometres (3.3 mi) northeast of the town of Orangeville.

Hockley Valley Provincial Nature Reserve is a nature reserve located on the Niagara Escarpment within the township of Mono, Ontario, Canada. It is managed by Ontario Parks. Approximately 80% of the Cannings Falls Area of Natural and Scientific Interest is within the borders of the park; land acquisitions are planned to encompass it entirely. The Bruce Trail links the reserve to other protected areas of the Niagara Escarpment.

The Hockley Valley Resort is a ski retreat, 18-hole championship golf course, conference centre and hotel in Mono, Ontario, Canada. It has 15 runs and four ski lifts. The town of Mono also has the Hockley Valley Provincial Nature Reserve. The resort, originally a small hotel along with a ski retreat was purchased by Nancy Adamo in 1985 and, in 1986, it underwent a $250 million revamp into a resort, spa and conference centre. By 2000, it employed 250 staff.The property was previously Hockley Hills Resort. Later, it became Heritage Village Canada, affiliated with Jim Bakker's Heritage USA. Plans were abandoned and it ran independently shortly afterward. Eventually, it became Hockley Valley Resort.

Orangeville/Laurel Aerodrome (TC LID: COL2) is located 4.0 nautical miles (7.4 km; 4.6 mi) west of Orangeville and just south of Laurel, part of Amaranth, Ontario, Canada.