In 1805, the Legislative Assembly of Upper Canada bought the lands between Etobicoke and Hamilton from the Mississaugas Aboriginal people, except for the land at the mouths of Twelve Mile Creek (Bronte Creek), Sixteen Mile Creek, and along the Credit River. In 1807, British immigrants settled the area surrounding Dundas Street and on the shore of Lake Ontario.
In 1820, the Crown bought the area surrounding the waterways. The area around the creeks, 960 acres (3.9 km²), ceded to the Crown by the Mississaugas, was auctioned off to William Chisholm in 1827. He left the development of the area to his son, Robert Kerr Chisholm, and his brother-in-law, Merrick Thomas. Chisholm also formed shipbuilding business in Oakville Navy Street and Sixteen Mile Creek (Halton Region) and lasted until 1842, but shipbuilding in Oakville lasted into the late 20th century.
The population in 1846 was 1,500. The community shipped large quantities of wheat and lumber via schooners and the railway. There were three churches, a grist mill and saw mill, and various small companies making threshing machines, wagons, watches, saddles, and metal goods. There were also tradesmen of various types.
Oakville's industries included shipbuilding. In the 1850s, there was an economic recession and the foundry, the most important industry in town, was closed. Basket-making became a major industry in the town, and the Grand Trunk Railway was built through it. In 1869, the population was 2,000. The community was served by the Great Western Railway and it was a port on Lake Ontario.
The town eventually became industrialized with the opening of Cities Service Canada (later BP Canada, and now Petro Canada) and Shell Canada oil refineries (both now closed), the Procor factory (no longer manufacturing), and, most importantly, the Ford Motor Company's Canadian headquarters and plant, all close to the Canadian National Railway and the Queen Elizabeth Way highway between Toronto and Fort Erie (Buffalo).
In 1962, the town of Oakville merged with its neighbouring villages (Bronte, Palermo, Sheridan, and the remainder of Trafalgar Township) to become the new Town of Oakville.
The Queen Elizabeth Way runs around the west end of Lake Ontario from Niagara Falls through Hamilton, Burlington, Oakville, Mississauga and becomes the Gardiner Expressway into downtown Toronto. Through Oakville it merges with Highway 403. Exit at Trafalgar Road for a quick route south into the downtown area. Highways 401 and 407 (an expensive toll route) also pass further north of the town.
Oakville and the surrounding area are home to many daily commuters into Toronto, where most highways during peak hours are stop-and-go. As the main road from Toronto to Hamilton, the Queen Elizabeth Way often slows to a standstill. Exiting at Ford Drive and going south to Lakeshore or Cornwall Drive or north to Upper Middle Road (all major, parallel routes) may be a better idea if traffic is unusually bad.
Oakville has two railway sections:
- 1 Oakville GO station, 214 Cross Ave (just off Trafalgar Road). Serving GO Transit trains and buses plus Via Rail trains, the station lies about 1½ KM north of downtown Oakville; to get downtown, walk south on Trafalgar Road or take Oakville Transit bus 14 south.
- 2 Bronte GO station. Serving only GO Transit trains, the station is about 5KM from Bronte Village on Lake Shore Road near Bronte Road, which can be reached by Oakville Transit bus 3.
Both GO Transit and Via Rail provide rail services to Oakville:
- GO Transit. Oakville lies on GO Transit's Lakeshore West commuter train line which runs from Union Station in downtown Toronto to Aldershot (Burlington), with rush hour trains continuing to downtown Hamilton. This is GO's most frequent service with peak hour trains running up to every 15 minutes, outside of rush hour trains run every half-hour. Trains operate roughly from 5:30AM weekdays (7:30AM on weekends and holidays) to about midnight. The trip from Toronto takes between 25 and 40 minutes.
- Via Rail, Oakville GO station. Oakville station lies on Via Rail's Quebec City-Windsor corridor, and is served by a number of trains daily along two lines: the Toronto-Windsor line serving Aldershot(Burlington), Brantford and London; and the Toronto-Niagara Falls line, with stops at Aldershot and St. Catharines, with one train continuing daily to New York City via Buffalo, Rochester, Syracuse and Albany.
- GO Transit, Oakville GO station. GO Transit operates the 407 West bus (route 46) from Oakville GO station to Square One in Mississauga, Bramalea in Brampton and Highway 407 station north of Toronto on subway Line 1 Yonge-University. Within Oakville, this bus also stops at Sheridan College. The 407 West bus runs every half-hour all day.
- 3 Megabus, Holiday Inn, 590 Argus Road (just off the QEW). Megabus operates coach service between Toronto and Niagara Falls stopping at the Holiday Inn in Oakville.
Walking is convenient around the downtown core and Bronte areas, and parking is easily available. Elsewhere driving or public transit is easier.
Oakville Transit operates bus routes around the city. Fares can be paid by exact cash fare or by the Presto card used by GO Transit and other municipal transit systems within the Greater Toronto Area. The fares as of February 2019 are:
- Children 0-5 years of age ride for free when accompanied by a fare paying adult.
- Adult 20 to 64 years: cash $4, Presto $3.10
- Youth 6 to 19 years: cash $4, Presto $2.38
- Senior 65 years and over: cash $4, Presto $1.96, free on Mondays
A fare allows for 2 hours of travel on Oakville Transit (OT) including changing OT buses, or transferring to connecting MiWay (Mississauga) and Burlington Transit buses. If paying by cash, ask for a "transfer" to use as a receipt. For Presto users, transfer info is automatically stored on your card when you tap on.
If transferring from GO Transit (GO) to Oakville Transit (OT) to complete a trip, a reduced OT fare of 80 cents (as of 2019) is available. For Presto cardholders, just tap your card on both transit systems to get the discount which is calculated after the transfer. With Presto, the reduced fare is also available to transfer from OT to GO. If paying cash on OT, the reduced fare is available if you show your GO ticket to the OT bus driver when you pay the fare in exact cash.
- Oakville's Downtown, Lakeshore Road (between Navy St & Allan St). The downtown area has a quaint small-town feel. Lots of specialty stores as well as high-end boutiques and eateries.
- 1 Oakville pier and lighthouse. Walking from downtown Oakville down Navy Street to Lake Ontario, you reach Oakville harbour. There is a pier which can be walked on, as well as a lighthouse. On clear days, Toronto's skyline can be viewed due to the curvature of Lake Ontario.
- 2 Erchless Estate, 8 Navy St (near the end of Navy Road by Lake Ontario), ☏ . Tu-Su 1-4:30PM. A museum chronicles 19th-century life and the Erchless family, founders of the town of Oakville. Donation appreciated.
- 3 Merrick Thomas House, 14 Front St (Lakeside Park). Open 1:30-4:30PM; July-August: Tu-Th Sa Su; May Jun Sep: Sa Su only; all holiday Mondays. The Merrick Thomas House was built in 1829, and is furnished with items of the era 1830–1840s. Donations welcomed.
- 4 Sovereign House (Bronte Historical Society), 7 West River St, ☏ . Late May to late Oct: Sa Su W 1:00-4:00PM, but call to confirm opening. Sovereign House was built between 1825 and 1846, and today it is a heritage display centre with artifacts and photographs. Donations welcomed.
- 5 Howard Iron Works Printing Museum & Restoration, 800 Westgate Road, ☏ . M-F 10AM-4PM by appointment only. Collection of printing machinery from the 1830s to the 1950s.
- Some of the best ambience is found south of the downtown area between Navy Street and Reynolds Rd. Many century-old homes are also located in this area.
- If you like to dream or enjoy interesting architecture, driving along Lakeshore Road east of the downtown area showcases many grand homes and mansions.
- 6 Sheridan College. One of the best animation colleges in the world. Animation fans should visit.
- 7 Glen Abbey Golf Course, 1333 Dorval Dr, ☏ . This course, designed by Jack Nicklaus, frequently hosts the Canadian Open. It is an attraction in itself with many dramatic holes that take advantage of the canyon-like valley of Sixteen-Mile Creek for abrupt elevation changes, natural hazards, and scenic beauty. There are hiking trails throughout the Sixteen Mile Creek Valley, and a walk or drive over the Upper-Middle bridge will give a view of the valley holes and forest which is especially appealing in fall when the colours change. Glen Abbey also houses the Canadian Golf Hall of Fame and a restaurant (in the clubhouse) for fine dining.
There are many parks in Oakville.
- Try walking along the pedestrian pathways bordering Lake Ontario, along the waterfront.
- The Trans Canada Trail, winding from coast to coast, runs through the town.
- 1 Bronte Creek Provincial Park. The closest provincial park to Toronto, is located on Burloak Road north of the Queen Elizabeth Way at the western edge of the town. It boasts a large pool perfect for kids, trails, a barn converted to playstructure, historic farm and home and a campground area.
- Oakville also has many other parks for kids and a great atmosphere all year round.
- 1 Downtown Oakville. The place to be, where Lakeshore Road is lined with a variety of fashionable stores and galleries in historic buildings.
- 2 Hopedale Mall (at Third Line and Rebecca Street). Over 50 stores and services including Shoppers Drug Mart, Hopedale Hardware.
- 3 Oakville Place (at Queen Elizabeth Way and Trafalgar Road). Many shops including The Bay, H&M, Mexx, Roots, Purdy's Chocolates, The Body Shop.
- 4 Bronte Village, Lakeshore Rd. W. at Bronte Rd.. Mostly modern buildings, but a small-town atmosphere. Street-front shops line parts of Bronte and Lakeshore Rds., and there is also the Bronte Village Mall, at the corner of Lakeshore and Jones.
- 1 Celadon House, 630 Ford Drive (Celadon House), ☏ . Sharing their passion "live to eat...", authentic Asian comfort food in a spacious and relaxing atmosphere. Mains $10-20.
- 2 Maro's, 135 Kerr St, ☏ , ✉ firstname.lastname@example.org. M-Sa 11AM-10PM, Su 11AM-8PM. Traditional Middle Eastern cuisine. Vegan and vegetarian choices.
- 3 Jac's Bistro, 379 Kerr St., ☏ . M-Th noon-10PM, F noon-2:30PM, 5PM-10PM, Sa 4PM-10PM. Rustic Italian and French cuisine.
Oakville has little nightlife to speak of for a city of 190,000 people.
- 1 The King's Arms, 323 Church Street. One of the busier bars in Oakville, located right downtown. Open until last call (2AM) even on Sunday or Monday. Some nights features live music and acoustic sets. Also features a great outdoor patio.
- 2 The Fire Hall, 2441 Lakeshore Road. Great food and service, excellent patio as well. Located in the heart of Oakville's Bronte area, by the lake.
- 3 Brü, 138 Lakeshore Road East, ☏ . 7 days a week, lunch and dinner. Excellent selection of craft beer, many of them local. About six beers on tap and 30 in bottles. Also have good snacks and pub food. Free parking after 6PM.
- 4 The Pipes and Taps Pub, 231 Oak Park Blvd #101, ☏ . Su-W 11AM-midnight, Th-Sa 11AM-2AM.
- 1 Sandman Hotel Oakville, 3451 South Service Rd W (on the west side of Oakville at the Burlington boubdary), ☏ , toll-free: , ✉ email@example.com. From $88.
- 2 Monte Carlo Inn Oakville Suites, 374 South Service Road (east side of the town), ☏ , toll-free: . Free Wi-Fi, in-room microwave and refrigerator. From $126.
Oakville is a very safe town. Unless you get reckless, visiting Oakville shouldn't pose any danger to you.