District 5 Little League is comprised of 4 leagues from Windsor and the surrounding communities, namely Windsor Central, Windsor West, Windsor South and Windsor South Canadians.

Windsor is the southernmost city in Canada and lies at the western end of the heavily populated Quebec City-Windsor Corridor in Southern Ontario. Windsor is located south of Detroit, Michigan and is separated from that city by the Detroit River, and has views of the Detroit skyline. Windsor marks the only border crossing point along the Canada-United States border where one travels north to enter the continuous United States from Canada. Windsor is nicknamed the Rose City and residents are known as Windsorites.

Windsor was first settled in 1749 as a French agricultural settlement, making it the oldest continually inhabited settlement in Canada west of Montreal. The area was first named Petite Côte ("Little Coast") and later became known as La Côte de Misère ("Poverty Coast") because of the sandy soils near LaSalle.

In 1794, after the American Revolution, the settlement of Sandwich was founded. It was later renamed to Windsor, after the town in Berkshire, England. The Sandwich neighbourhood on Windsor's West Side is home to some of the oldest buildings in the city including Mackenzie Hall originally built as the Essex County Courthouse in 1855. Today, this building functions as a community centre. The oldest building in the city is the Duff-Baby House built in 1792.

Windsor's economy is primarily based on manufacturing, tourism, education, and government services. It is one of Canada's major automobile manufacturing centres and is often referred to as the Automotive Capital of Canada. However, plant closures and significant job losses in recent years have significantly impacted Windsor's manufacturing industry.

Windsor has a well-established tourism industry. Caesars Windsor ranks as one of the largest local employers and has been a major draw for visitors since its opening in 1994. The city also boasts an extensive riverfront parks system and fine restaurants such as those on Erie Street in Windsor's Little Italy, another popular tourist destination. Additionally, the Lake Erie North Shore Wine Region in Essex County has enhanced tourism in the region. Hiram Walker Distillery is on the waterfront and offers tours on the history of the Olde Walkerville area, a major part of the rum running days of Al Capone.

Windsor is at the dividing line of a humid continental climate and humid subtropical climate with four distinct seasons. The mean annual temperature is 9.5°C (49°F), amongst the warmest in Canada. Some locations in British Columbia have a slightly higher mean annual temperature due to milder winter conditions. The coldest month is January and the warmest month is July.

Summers are hot, humid and the annual average rain is 94 cm (37 inches), and thunderstorms are common. Windsor has the highest number of days per year with lightning, haze, and daily maximum temperatures well over 30 °C (86 °F).