Winston Park, Oakville Neighbourhood Guide: Make Home a Retreat

The Winston Park neighbourhood in Oakville is part of the town’s northeastern border. The area is full of business parks, retail storefronts, and industrial buildings, with few residences throughout. Locals enjoy quiet streets and privacy due to the neighbourhood’s low density. The area’s borders are Dundas Street West to the north, Winston Churchill Boulevard on the east, Queen Elizabeth Way (QEW) to the south, and Ninth Line on the west. 

In the early 1800s, a farming village occupied the area that is now Winston Park. The village was initially named Hammondsville after the general store’s proprietor, William Hammond. The store was at the intersection of what is now Winston Churchill Boulevard and the Queen Elizabeth Highway (QEW). The village’s name changed to Sheridan in 1857 in honour of Richard Brinsley Sheridan, an Irish playwright, satirist, poet, and owner of the London Theatre Royal. 

The agricultural community prospered until around 1937 when the construction of the QEW cut through the village. Sheridan amalgamated with the Town of Oakville in 1962 and remained a rural neighbourhood until the 1980s. While the community no longer remains, the name carries through the area, with notable sites like Sheridan College, Sheridan Centre, and Sheridan Nurseries commemorating the memory. 

The Winston Park neighbourhood is mainly commercial and industrial properties with a few houses within its boundaries. The limited residential buildings are detached homes, typically with two or three bedrooms. Due to the lack of houses, the area’s residents enjoy relatively serene and private living and are close to many amenities. Most of the buildings in the area were constructed either before 1960 or between the 1960s and 1980s. 

The Oakville Arts Council emphasizes the importance of arts throughout the community. It organizes memberships, monthly networking events, annual awards ceremonies, and cultural grants while generally sustaining community engagement and artistic development. 

While the town has multiple venues for artists to exhibit their work, the Oakville Centre for the Performing Arts is a focal point for culture in the community. Frequent theatrical and musical shows bring guests into the small theatre where every seat is within 17 metres of the stage. The centre is in the heart of Oakville’s downtown, promising residents of Winston Park a fun night out.

The neighbourhood also includes the Oakville Entertainment Centrum. In the southeast corner of the area, locals will find the plaza populated by  Cineplex Cinemas, iFly Toronto (Oakville) Indoor Skydiving, Putting Edge, and Dave & Buster’s. Additionally, the 5 Drive-In Theatre on Ninth Line offers a movie-going experience under the stars. The theatre has three screens and concession stands for visitors to enjoy two back-to-back new releases or nostalgic hits per night.

Locals have access to many retail storefronts in and around Winston Park. Beginning at the corner of Winston Churchill Boulevard and Dundas Street West, people will find many of their needs accommodated. The area is home to a Galleria Supermarket, Canadian Tire, Winners, Staples, The Home Depot, Best Buy, Sport Chek, Healthy Planet, banks, pet supplies, and much more. 

Just outside the neighbourhood, shoppers can visit the Upper Oakville Shopping Centre at Upper Middle Road and Eighth Line. The outdoor mall features over 50 storefronts, including a Metro, Shoppers Drug Mart, LCBO, pet care, medical services, a dollar store, and a bakery. 

A night out in the Oakville Entertainment Centrum offers dining experiences like 3 Brewers, a microbrewery serving European food, K&B Sushi, and Bâton Rouge Steakhouse & Bar. There’s also Wild Wing, Trattoria Timone Ristorante, Sukothai, and more. A great way to finish a meal in the plaza is to visit Demetres, the only dessert restaurant in Oakville.

Residents can find even more variety along Dundas Street East and Winston Churchill Boulevard. Dundas eateries include Montana’s, Lone Star Texas Grill, Buffalo Wild Wings, Chipotle Mexican Grill, Basil Box, and Frankie’s Nashville Hot Chicken. On Winston Churchill, diners can visit St. Louis Bar & Grill, Browns Socialhouse, Sunbeam Grill, Karahi Point, or Gino’s Pizza. 

Ontario Hydro-Winston Park is the main parkland in the neighbourhood. This central green space also includes Winston Woods. Residents looking to enjoy the outdoors can park their cars and use the walking trail through the hydro corridor and forested zone. 

For more outdoor amenities, residents can visit Bronte Creek Provincial Park by travelling south on the QEW to Burloak Drive. The park offers activities such as disc golf, fishing, hiking, cross-country skiing, snowshoeing, and tobogganing. An on-site Discovery Program teaches visitors about early local farmers or unique natural features of the land, and a children’s farm provides an interactive learning experience. The site also includes a campground, pet areas, and an almost one-hectare outdoor pool.

The neighbourhood’s closest public recreation centre is the Iroquois Ridge Community Centre. The facility consists of a 25-metre competitive indoor pool, leisure pool with waterslide, fitness centre, gymnasium, library branch, and meeting rooms. Glenashton Park surrounds the centre and includes a skate park, pickleball and tennis courts, cricket ground, dog park, splash pad, and the town’s only bocce ball court. An older adult centre provides accessible programs and socials for local seniors. 

Commuting in and out of Winston Park is simple, with easy access to Highway 403 and the QEW. By taking the QEW and the Gardiner Expressway, motorists can reach downtown Toronto in about 35 minutes. 

The neighbourhood is also conveniently located for travel by public transit. Residents can take the 45 MiWay bus route to Clarkson GO Station, where they will ride the Lakeshore West train to Union Station. The whole trip should take about an hour and 15 minutes. 

The few people living in Winston Park enjoy the seclusion of a low-density neighbourhood while being close to all Oakville has to offer. Given the many activities and amenities available in town, entertainment is always an option.