Although settlement dates back to 1800, it was not until 1836 that a downtown business centre was established by Whitby's founder Peter Perry.

Whitby's chief asset was its fine natural harbour on Lake Ontario, from which grain from the farmland to the north was first shipped in 1833.

The building, constructed as an Elizabethan-style castle in 1859–62 as a private residence for the Sheriff of Ontario County, is a significant architectural landmark and Whitby's only provincial historic site marked with a plaque.

During the Second World War, Whitby was the location of Camp X, a secret spy training facility established by Sir William Stephenson, the "Man Called Intrepid".

Although the buildings have since been demolished, a monument was unveiled on the site of Camp X in 1984 by Ontario's Lieutenant Governor John Black Aird.

Following the war, Soviet dissenter Igor Gouzenko was taken to the facility with his wife to live in secretive protective custody after fleeing Ottawa, Ontario.

Planning for the construction of a town hall intended to centralize municipal staff working in satellite offices began in 1970 under mayor Des Newman.

Construction began on the Raymond Moriyama designed building in 1975; it was opened by Mayor Jim Gartshore on January 8, 1977.

Whitby borders Ajax to the west, Pickering to the northwest, the Township of Scugog to the north, and Oshawa to the east.

[6] As per the 2021 census, the most common ethnic or cultural origins in Whitby are English (19.9%), Irish (17.1%), Scottish (16.7%), Canadian (13.7%), Italian (6.4%), German (6.2%), Indian (6.0%), French (5.4%), British Isles (4.8%), Chinese (4.3%), Jamaican (3.5%), Dutch (3.4%), and Polish (3.0%).

This was followed by Urdu (1.7%), Tamil (1.6%), Mandarin (1.5%), French (1.3%), Spanish (1.1%), Italian (1.0%), Tagalog (0.9%), Cantonese (0.8%), Arabic (0.7%), Hindi (0.7%), Dari (0.7%), and Portuguese (0.6%).

Other companies present in Whitby include pharmaceutical manufacturer Patheon, Lear Corporation, Automodular Assemblies, McGraw-Hill Ryerson, and several others.

Built in 1859 by the Sheriff of Ontario County, Nelson Gilbert "Iron" Reynolds, Trafalgar Castle remains a unique Canadian treasure.

Ontario Highway 401 runs through the south end of Whitby, with interchanges at Brock Street and Thickson Road.

It originally extended from Highway 401 northward as part of Brock Street, but this portion was downloaded to Durham Region in 1997.

Finally, GO Transit provides frequent service via its Lakeshore East line, which (in Whitby) runs parallel to the CN tracks.

GO Transit buses also connect Whitby with Durham Region (including Port Perry and Beaverton to the north) and areas further afield.

[18] The paper consists primarily of resident contributions, with occasion updates on local and regional politics from Mulcahy.

This team featured long-time president of the Boston Bruins, Harry Sinden and former mayor of Whitby, Bob Attersley.

The Brooklin Redmen Senior A lacrosse club is one of the most successful in Canadian sporting history, while the Junior A Whitby Warriors have been awarded the Minto Cup four times since 1984.

The facility includes six icepads, a swimming pool named for local Olympian Anne Ottenbrite, six tennis courts, five ball diamonds, three batting cages, a skatepark, a soccer pitch, The Sports Garden Cafe restaurant and the Whitby Sports Hall of Fame.