The Halfway House's bartender would give the train operators a free beer each at the four-minute mark, to delay their leaving and provide the thirsty passengers more time to spend money.
[2] The area of Colombia International College and Camelot Towers and Highway 403 was, from the earliest days of European settlement, a popular picnicking spot.
In 1908, the Burke Real Estate Company bought the Bamberger farmland, breaking it into smaller lots and building new public streets.
Sales posters boasted of "The Ideal Suburban Survey," with 40' x 140' lots that were advertised as being "20 Minutes from Centre of City" on 5-cents-a-ride electric trains.
There were several stores, a volunteer fire brigade and a resident police constable named George "Fatty" Smith.
An open field on Emerson Street, near Royal Avenue, held sporting events and garden parties.
In the late 19th century, soldiers from the 13th Royal Regiment of Hamilton – now called the Royal Hamilton Light Infantry – used land around today's Rifle Range Road for rifle practice, shooting at concrete bunkers on the Escarpment where targets were set up.
There are remains of the target bunkers in the forest south of Alexander Park, while further up the escarpment slope, across the 403 highway, are the remains of a tall stone wall built to protect the cars of the Brantford & Hamilton Railway (the wall may be seen from the recreational Chedoke Radial Trail).
In World War I, young soldiers from all over the Hamilton area trained for the battlefields of Europe in Ainslie Wood.
The rock-chunks were hauled in horse-drawn wagons from the Escarpment, where the rock had previously been dynamited to build a railway line; the gravel came from a quarry in Dundas.
In World War II, many small, inexpensive homes were built in Ainslie Wood East for Hamilton's war-expanded industrial labour force.
There was light industry, such as Donald Wire and Rope (where Fortino's and St. Mary's school are now), John Deere (where the Mondelez International candy factory is now) Ralph & Sons Fuels (where Wendy's is now) and candymaker Walter E. Jacques & Sons (on Ewen, where Onyx Condos was built).
During Prohibition, Ainslie Wood had a resident bootlegger, Chuck Gowdy, who sold moonshine liquor from his shack.
After 1934, when retail sales of alcohol were legal again, customers filled Paddy Green's tavern on Main Street West by Longwood Road.
Russ Jackson was a post-war celebrity from Ainslie Wood: a star quarterback at McMaster who went on to win three Grey Cups with the Ottawa Rough Riders in the 1950s and '60s, becoming Canada's most famous athlete.
The Women's Institute also lobbied for Ainslie Wood's first traffic light, at the corner of Main Street and Broadway Avenue.
In recent years, Ainslie Wood has faced many challenges, such as illegal lodging homes for students,[3] a lack of recreational facilities[4] and greenspace, the closure of Prince Philip School, poverty, traffic and zoning issues.
Ainslie Wood has many strengths, including proximity to McMaster and the forest-covered Escarpment, the Rail Trail, Stroud Park, Alexander Park, two Catholic Schools (Canadian Martyr's and St. Mary's), a Hebrew academy, Columbia International College, several churches of various denominations, a thriving commercial zone along Main Street West and two active community associations: the Ainslie-Wood / Westdale Community Association (AWWCA) and the Ainslie Wood Community Association, or A.W.C.A.
Multiple high-rise student and mixed-use residences are being planned in the area, at 17 Ewen Rd & 20 Rifle Range Rd, 1629-1655 Main St W and 69 Sanders Blvd & 1630 Main St W.[5] Currently, there are 8 bus routes (including branches) operated Hamilton Street Railway running through Ainslie Wood.