The "contraption"

looks like a

Reaper-binder

^{A Massey-Harris reaper-binder pulled by a tractor (Rutland, England, 2008)}

The reaper-binder, or binder, is a farm implement that improved upon the simple reaper. The binder was invented in 1872 by Charles Baxter Withington, a jeweler from Janesville, Wisconsin.1 In addition to cutting the small-grain crop, a binder also 'binds' the stems into bundles or sheaves. These sheaves are usually then 'shocked' into A-shaped conical stooks, resembling small tipis, to allow the grain to dry for several days before being picked up and threshed.

The make/model seems to be printed on it, but I can't really decipher it. Many companies produced these and form follows function, largely:

– John Deere GRAIN BINDER FRAMED PAPER SIGN 30 X 25

^{Man driving a tractor with a reaper binder, harvesting wheat on a Canterbury farm. Photograph taken circa 1930, by Green & Hahn of Christchurch.}

_{— H. Jeffs: "Homes And Careers In Canada", 1914.}

From comments we learn:

Based on the partial lettering visible, the manufacturer of the reaper binder might be Cockshutt. Cockshutt was a company based in Ontario, Canada, which would jibe with OP's Alberta location. — njuffa

Which sounds plausible:

Somehow I wasn't able to find a model made before 1937…

But the tractor

seems to be a Fordson?

— Fordson E27N Major, 1945 - 1952

N series 1929 - 1945

Earlier versions after 1917 might match as well, Series F on video here versions 18–34.

Combinations of Fordson tractors pulling reaper-binders Model T Ford Forum: Forum 2011: Old Photo - More Fordson Tractors At Work On The Farm

^{Fordson tractor towing a reaper-binder with Len & Keith Markham at White Hall Farm in the 1950s
Fordson with reaper/binder The tractor here is a Fordson model N, produced between 1939 and 1945. In 1940 the rear mudguards were changed to the shape in the photo below, so this is an early version.}

Dating

Based the tractors lack of pneumatic/rubber tires of the tractor, this might indicate a date well before the 1940s.

More on the timeline: Top Ten Farming Innovations: Number Ten Rubber Tires, II. Reaper/binder.

On the tractor alone, no more precise date may be inferred than between 1917–1952. Based on exhaust and air-filter, I'd opt for the middle of that period. But those could be changed by modders.

The machine the tractor is pulling is a grain reaper-binder, possibly a McCormick-Deering.

The reaper-binder, or binder, is a farm implement that improved upon the simple reaper. The binder was invented in 1872 by Charles Baxter Withington, a jeweler from Janesville, Wisconsin. In addition to cutting the small-grain crop, a binder also 'binds' the stems into bundles or sheaves. These sheaves are usually then 'shocked' into A-shaped conical stooks, resembling small tipis, to allow the grain to dry for several days before being picked up and threshed.
Withington's original binder used wire to tie the bundles. There were problems with using wire and it was not long before William Deering invented a binder that successfully used twine and a knotter (invented in 1858 by John Appleby). Early binders were horse-drawn, their cutting and tying-mechanisms powered by a bull-wheel. Later models were tractor-drawn and tractor-powered. Binders have a reel and a sickle bar, like a modern grain head for a combine harvester. The cut stems fall onto a canvas bed which conveys the cut stems to the binding mechanism. This mechanism bundles the stems of grain and ties the bundle with string to form a sheaf. Once tied, the sheaf is discharged from the side of the binder, to be picked up by the 'stookers'.
With the replacement of the threshing machine by the combine harvester, the binder has become almost obsolete. Some grain crops such as oats are now cut and formed into windrows with a swather. With other grain crops, such as wheat, the grain is now mostly cut and threshed by a combine in a single operation, but the much lighter binder is still in use in small fields or mountain areas too steep or inaccessible for heavy combines.

Based on what little I can see of the tractor...
The rear wheel is steel, matching the spoke arrangement and the shape of what I'm assuming is the tank above the engine - the best match I've found is the Fordson F tractor.

The Fordson Model F remained in production from 1917 to 1920 at the Henry Ford & Son plant in Dearborn, Michigan, and in 1921, its production finally began at the Ford Motor Company, first in the U.S.A. and then in the U.K. As in many of its contemporary tractors at the time, the Fordson ran on Kerosene and it required a small adaptation to run on gasoline.

Farmers are creative by nature and necessity. It may be that parts from one machine were put on another and home modifications added making it difficult to identify.