The Woodstock Typewriter first appeared in 1914, the product of a company formed from the failed Emerson Typewriter Company which had not only changed ownership but designs as well.  Sears-Roebuck investment in Emerson, and Emerson's failure, led to ownership by Sears-Roebuck and the installation of Alvah C. Roebuck as president.  Roebuck, a man with much experience in things mechanical, designed a completely new machine and re-launched the company in 1914 as the Woodstock Typewriter Company.  It was a success from the beginning, lasting through the Great Depression and later, until buyout by R. C. Allen Business Machines in 1950 who continued production.
Woodstock No. 4

Tilman Elster collection

Serial A-19848, manufactured about 1915.  The No. 3 and No. 4 Woodstocks were the first models offered by the company, with the No. 3 being produced only for a year or two before being supplanted by the No. 4.

As we go through the pictures and machines, we'll make reference to alterations.  Here, note the design of paper bail, which is a horizontal rod on the carriage, on which are mounted two sliding paper holders. 
Woodstock No. 4

Jim Dax collection

Serial 26454-6, built about 1916.  This machine is essentialy the same as that above, except for the paper table decal.  This decal difference is not yet fully identified as to meaning, although this decal seen here is normally thought to be older.
Woodstock No. 5

Jim Dax collection

Our first of many No. 5 models -- this model was introduced in 1917.  Note the addition of a ribbon selector switch on the front.  The rail-type paper holder, or bail system is gone, having been replaced with two sliding paper holders with rollers mounted inside.  This might have been done to allow more clearance for manifold work.  A left-side paper edge guide has appeared on the paper table as well.  Built about 1918.
Woodstock No. 5

Jim Dax collection

Wide-carriage machine with serial BW-43670, built about 1919.  This machine is the same in all other particulars as that above, with the exception of wider platen and carriage.
Woodstock No. 5

Ned Brooks collection

Ned -- who goes by "Cuyler" in some circles -- has sent a selection of his machines as well, and we start his (in proper serial order) with this example. 

Serial number J-120743, built about 1920.  Note that this machine is also a wide-carriage example, and in other features matches the No. 5 machines seen prior.  This machine has been refinished and likely was rebuilt at some later date.
Woodstock No. 5

Tilman Elster collection

Serial 162632, built about 1926.
Woodstock No. 5

Ned Brooks collection

Serial number N-164588, built about 1926.

The decal differences are perplexing -- some of those with the decal seen on 162632 are known to have been distributed by Woodstock's subsidiary in England.

Note that, until this point, the same reliable machine has been in construction for nearly a decade with no major changes.
Woodstock No. 5

Ned Brooks collection

Serial number N-317115, built about 1931.  Here, we have the first serious alterations to the machine.  Note that the front, sides and rear are now enclosed by panels designed to fit the frame openings.  Not only does this machine add a shift lock key to the right side, duplicating that on the left, it also has the later-style shift mechanism which includes a shaft running along the
front frame of the machine.  Look at the keyboard of the No. 5 seen above, and note that the shift key levers simply run back into the machine.  On this 1931 machine and later units, a new leverage system was employed, which can barely be seen in these shots, but is present nonetheless.  Note also the hinged ribbon spool covers.
Note the enclosure of the front by a smooth-painted panel, and the sides and rear by crinkle-finished panels.
Woodstock No. 5

Will Davis collection

Serial N400869E, built 1934.  Further stylistic changes now have occurred, with the top of the machine being enclosed by a new deck.  Note in the frontal shot that a smooth-painted section is present, in half-circle shape, immediately in front of the type basket. 
Woodstock No. 5

Tilman Elster collection

Serial number 417557, built in 1934.  Notable is that the half-circle trim on the machine's front is now gone, making that feature obviously very short-lived.  One feature that is much harder to spot on this machine concerns the key that is above the left shift lock key, nearly in line with the third row of character keys.  This is a "Tab Stop Set" key, indicating that this machine has key-set tabulator.  These cannot be cleared individually; a lever on the carriage is used to clear all stops at once.
Woodstock No. 5

Ned Brooks collection

Serial number N522442E, built 1938.  This machine is the same as that seen above in body style, and on the rear we can see the shroud applied around the mechanism that actually sets the tab stops in the tab stop rack on the carriage.  Note that a proper, modern paper bail now appears for the first time on the machines seen here; this is known to have appeared by serial 486155.
Woodstock Standard

Tilman Elster collection

This machine's serial number still falls into the block of "No. 5" machines, although it is by now very different from the first machines of that model. 

This machine is serial number N599765F, and was built in 1941.  This body contains essentially the same machine, although the "Tab Stop Set" key is now on the front, and not in the keyboard.  Note also the windows in the paper table, allowing view of the margin set placement.  This machine does have a wide carriage.
1947 Woodstock advertising illustration seen here shows that the body essentially is the same as the immediate pre-war version, but note that a new key is on the machine front for clearing individual tab stops, and that the paper table window is now full-width. 

The most significant change occurred in this year -- the machine was finally converted to basket, or segment, shift.

This body style essentially continued until the 1950 buyout by R.C. Allen, which brings our sequential look at production machines to a close.  Below, we'll see other variants as noted.
Annell' No. 3A

Tilman Elster collection

This machine is said to be a version of the Woodstock No. 3, obviously enclosed, which was sold by mail-order.  The author owns an original advertisement for this machine, which is dated 1922 -- many years after the No. 3 was dropped.  These machines appear to run in their own serial number block; this example is serial number A1376. 

These were advertised as brand-new and not rebuilt machines.  The distributing agent, namely the Anell' Typewriter Company, was located in Chicago, Illinois.  A section of the ad is seen below.
There are some troubling facts concerning the assumption that these were simply Woodstock No. 3 machines sold later.  Note that these are enclosed (sides, front) in 1922, whereas the true Woodstock No. 5 did not receive this treatment until 1931.  Some but not all also have a true paper bail, fifteen years before the Woodstock did.  One wonders if some OTHER company bought the old-stock parts and assembled them, modified, into this new machine.  Note also that the print alignment fork on the segment matches no yet-seen Woodstock machines.  Curious.  Is all of this why the machine is Model 3A, and not some other number?
Woodstock No. 5 - factory rebuilt

Will Davis collection

This machine actually contains the frame of the oldest No. 5 Woodstock on this page.  Its serial number is RN15206, which indicates that it was originally an extremely early No. 5 -- but the "R" prefix indicates factory rebuilding, which should be obvious.

The rebuilding of this example is also a substantial upgrading.  The whole carriage is new, and contains the post-war type paper table and paper bail.  The whole machine is enclosed, and a retro-fit front panel unlike anything used on production machines is employed.  Note that the logo matches that on the pre-war / post-war body seen above.  Finish is overall black crinkle.  Decal on the rear indicates Woodstock Typewriter Co, and it is known that Woodstock advertised its own machines rebuilt in its own factory.

E-mail correspondence from time to time, and sightings of machines on the internet seem to indicate that these rebuilt early machines might be more common than once thought.  This might lead to identification difficulties if only serial numbers are employed, which is why it is important to show this machine here.  These have also been spotted finished in overall flat enamel, with older paper table, but done otherwise in the same way.
Woodstock Electrite

Tilman Elster collection

Naturally, we cannot get away without showing the most famous of the Woodstock machines, namely the Electrite of 1925-1926.  This was among the very earliest practical electric typewriters, in a developmental vanguard that included the Mercedes and the Remington / Electromatic machines.  This example is serial number E 30403.
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Woodstock Typewriter Factory, Woodstock, Illinois.  Post card view.  Probably late 1920's or early 1930's; post card in Will Davis collection.
Woodstock No. 6   s/n J100578    Don Sutherland collection

Don Sutherland's very first contribution to the site is this surprising machine; it's clearly labeled as a No. 6 model, with 14 inch carriage.  This contradicts the serial number lists which indicate wide carriage machines having a serial prefix of "8."  Jim's machine above has a "B" prefix with wide carriage and is a No. 5; this machine has a "J" and is a No. 6.  It's the only Woodstock No. 6 we know of at the moment (February 2008.)
Final patent date on left-most decal is 1921.  "Typewriter Topics" indicated in 1923 that the No. 6 appeared in early 1922, with the No. 7 (18 inch carriage) following soon thereafter.  As we can see on this page, the separate model numbering for wide carriage machines was not permanent.
Woodstock No. 4 / David B. Davis collection