More recently know as Oakwood Village, Oakwood-Vaughn is bordered by Eglinton Avenue West to the north, St. Clair Avenue to the south, Dufferin Street to the west and Winnett Avenue and Arlington Avenue to the east. Before amalgamation it was the former City of York. The northern half of Oakwood's area is nicknamed the Five Points after the intersection of Oakwood Avenue, Vaughan Road, and Belvedere Avenue. The western half of the area was once called Northcliffe. Along the northern border sits a portion of Little Jamaica, along Eglinton Avenue West. The area has worn many municipal hats and has had its boundaries changed on many occasions.
The neighbourhood is named after the road which was named after Benjamin Vauhn, a British commissioner who was famous for signing a peace treaty with the United States in 1783. The road was very popular with street racers in the 1950s due to its many curves that became a part of its course from it being built along a creek.
The neighbourhood after which the neighbourhood gets its name, Vaughn Road was built as early as 1850, which up until then it was a trail used by the First Nations. Its original alignment began as Yonge Street, ran parallel to Davenport Road to Bathursy, then along its current alignment into Dufferin. The curve in the road remains where it intersects with Eglinton Avenue before and Esso gas station was built. The area was originally settled in the early 1800s by Pennsylvania Germans who soon were joined by a wave of settlers from the British Isles. The area originally consisted of a gathering of small villas and hamlets and one of theses was named Vaughnville in honour of the British diplomat, Benjamin Vaughn, co-negotiator of the Peace of Paris Treaty that signalled the end of the American Revolutionary Way. Life was hand to mouth for many of the area's settlers until after the second world war when many Italians , and Eastern Europeans settled. The newcomers helped to transform Vaughn from an agricultural based area into an industrial and commercial centre. The ensuing growth would continue, culminating in its incorporation as a city in 1991.
Vaughn boasts houses and examples of homes that befit its history. One can fine heritage properties and newer town homes and detached homes that have been designed to fit with the historicity of the community and not outshine it. In these more heritage-centred districts, one can find original homes mixed in with a selection of ranch-style bungalows and infill housing development. It the downtown core, there are a few newer condominium buildings. Homes south of Rogers Road are two-storey buildings, with siding facade or a mix of brick and siding and they are generally built closer together than those in the Northern portion of the neighbourhood and have front porches that look out on their quiet one-way streets. Nearer to Eglinton, bungalows start popping up in the midst of two-storey semi-detached and detached brick homes. Along St. Clair Avenue West and Eglinton Avenue West, one finds many apartments that sit on top of retail stores on the strip.
Assembled in 1972 primarily for flood control purposes, G. Ross Lord Park has been the site for a number of naturalization projects and revegetation initiatives and is perfect for wilderness hike and strolls in any season. Earl Bales Park has ski-hills and cross-country trails in the winter and is an expansive park space in the summer. The Toronto Centre for the Arts is a multi-use theatre and entertainment space that holds three unique stages and hosts a wealth of different shows from orchestras to musicals and plays. There is an portion of Eglinton that runs through the area that is known as the International Market and it is blessed with Caribbean, Philippino and Latin markets and products.
The public schools in the area are RJ Lang, Willowdale, Charles H. Best and Yorkview in the middle category and Fisherville is a senior and there are two catholic schools named St. Antoine Daniel and St. Edward. Although, Oakwood-Vaughn is further north than the heart of the city and the neighbourhoods that are getting the buzz today, it holds an identity and diversity all of its own with fragrant and exotic restaurants and markets, and the underlying heritage of its history, it retains a unique sample of the diversity of the larger city that makes Toronto so unique.