Dempsey Park, Milton Neighbourhood Guide: A Well-Balanced Community

Dempsey Park, Milton

Image of Dempsey Park

Neighbourhood At a Glance:

Average Commute Time

Union Station can be reached in about an hour by car and two hours by public transit.


This is a family community close to shops, grocery stores, and sports centres.

The Housing Market

Primarily two-storey, detached houses with a few duplexes available.

What You’ll Love

Dempsey Park is within walking distance of major stores and sports centres.

What Not To Expect

There aren’t many fancy restaurants or boutiques in this part of Milton.

This is a newly constructed neighbourhood with all the necessities. There are nearby shopping centres with grocery stores and nationally recognized retailers, and it’s not far from clothing stores and smaller shops in downtown Milton. Dempsey Park is teeming with forested natural areas near parks with playgrounds, splash pads, and sports fields. There are also state-of-the-art recreational facilities close by where you can play hockey, go swimming, or watch a football game. A great feature of Dempsey Park is how near it is to Highway 401, so you don’t have to worry about hitting traffic on your way to or from work.

Neighbourhood Review


Most of the houses in this neighbourhood are two-storey, detached buildings with a front lawn and backyard. The homes are constructed of brick, stone, or have vinyl siding, and some have decorative trimming beneath the fascia on their roofs. Many homes have a large front porch, and most have steps leading down to their driveways. Columns and archways outside the front door are prevalent in this neighbourhood. It’s also common for houses to have a young tree or small garden on their front lawn. The odd house has a second-floor balcony, and most homes have a double-door garage. Dempsey Park is bordered by the 401, Thompson Road, Main Street, and James Snow Parkway.

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Things to Do in Dempsey Park

Arts & Culture

This neighbourhood is a short walk away from FirstOntario Arts Centre Milton. This modern building is where you can watch theatrical and musical events. It also has a viewing gallery where residents can enjoy the work of local and Canadian artists. This centre runs programs for people of all ages to learn about photography, sculpture, and painting. Milton also has many annual festivals such as the Milton Fall Fair. Some of the fair’s attractions include a midway with carnival rides and games, animal shows, a demolition derby, pumpkin competitions, and local vendors selling their wares.

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Dempsey Park is within walking distance or a short drive away from nationally recognized retailers on both sides of Highway 401. Some of these stores on the south side of the highway include The Home Depot, Sephora, PetSmart, and Longo’s Milton. On the other side of the highway, you will find a Michaels, an Indigo, a Canadian Tire, and a Staples. There’s also a Walmart Supercentre in this area, as well as a GameStop, and a few automotive dealerships. If you’re looking for smaller stores, clothing stores, or boutiques with unique items, you should travel southwest of here on Main Street. This will take you to Milton’s downtown core where you will find many independently run shops.

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Restaurants & Dining

There are a few restaurants northwest of Dempsey Park near The Home Depot. One of these is Sunset Grill, a popular breakfast chain where you can order classic diner dishes like pancakes, waffles, sandwiches, and hamburgers. Sunset Grill is a short walk from Turtle Jack’s Milton. The menu at Turtle Jack’s has classics like burgers and ribs, but also includes Mexican options like basa fish tacos and chicken fajita wraps. Besides the LA Fitness in this area, you will find Topper’s Pizza, a casual takeout restaurant.

recreation areas


One of the largest parks in this neighbourhood is Dempsey Neighbourhood Park. There’s a soccer field here, as well as a playground and a large, wooded area with a paved pathway. This park is a short walk away from Sprucedale Park, which has two ponds and another path running through a bit of forest. Dempsey Park is a short drive away from Lions Sports Park, which has several outdoor recreational amenities such as three baseball diamonds, and six soccer fields. The sports park also has a splash pad, a playground, a skate park, and a football field. Another small park with a playground is Sinclair Park.

dempsey park restaurants


Lions Sports Park is next to Milton Memorial Arena. This is the closest ice-skating rink for people living in Dempsey Park. Not far from here is the Milton Leisure Centre. This centre has a 25-metre lane swimming pool, a leisure pool with a waterslide, and a heating pool. The centre also has a weights gym and a spinning room. There are courses available for registration at the centre including classes for swimming, lifeguarding, spinning, and general fitness. If you’re not into physical exercise, you can stop by the Cineplex Cinemas Milton near Maple Avenue to catch a movie.  

green areas

Transit & Commute Times

The fastest route from Dempsey Park to downtown Toronto is taking Highway 401. Head northeast on Main Street East then turn left on James Snow Parkway. Soon you can exit onto the 401, which you follow for around 20 minutes before merging onto Highway 427 heading south. After about 10 minutes you’ll hit an interchange where you merge onto the Gardiner Expressway heading east. This will bring you into downtown Toronto by exiting onto one of the major streets leading you north into downtown. Arriving by public transit involves taking a GO bus to Union Station, which takes around two hours.

A Modern Neighbourhood

Parks, schools, and grocery stores are all within a short walk of Dempsey Park. This neighbourhood has many two-storey homes with intricate architecture, so every building looks unique. Not only are the homes beautiful, but this community has many recreational facilities for all sorts of sports-goers. Lions Sports Park has baseball diamonds and soccer fields and is right next to the Milton Memorial Arena and Milton Leisure Centre. Dempsey Park is a great place for commuters heading out of town for work as it is right next to the 401. Additionally, there are many restaurants nearby for outings with friends and family.

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Frequently Asked Questions

What is Dempsey Park, Milton, known for?

This is a new neighbourhood close to Milton’s commercial areas as well as schools and parks.

Why is it called Dempsey Park?

The neighbourhood is named after John Dempsey, who emigrated to the Milton area in the mid-1800s with his seven children. Dempsey built the “Winding Sixteen Farm,” and operated a community store selling dry goods, hardware, and groceries.

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Dempsey Park, Ontario


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