1891: Two identical letters
As he notes, these brief and basically identical letters, found at the Oregon Historical Society (Ms 777), might be to two different grandchildren. They’re indexed at OHS as being addressed to Louis Dement. They were written by James Winston (1823-1892), pioneer of 1846 from Virginia.
One of them seemed especially familiar to me; we discussed it with Henry Zenk a bit on the old CHINOOK listserv in 2000.
(That was courtesy of Jim Holton, who may have found it in researching his beautiful book “Chinook Jargon — The Hidden Language of the Pacific Northwest“.)
At the links I’ve just given, you can see what those people have put forth as translations of today’s letters, shown here.
I’m going to give it my own shot now.
The text is in typical “pioneers’ ” Chinook, that is, the early-creolized southern dialect plus many detectable intrusions of Anglophone influence. It’s fluent stuff nonetheless!
Damascus, Clackamas County, Oregon
Nov. [?!?!] 27 / 91
Hias Close Old Cracking Snap [Version 2: Old Bangle*],
hayas-ɬúsh úl cracking snap,
‘Dearest Old  Cracking Snap,’
Nika tickey mesika chaco copa nika house pe muckamuck Strawberries pe cherries pe conaway
nayka tíki  msayka cháku kʰupa nayka háws pi mə́kʰmək strawberries  pi chéris* pi kánawi
‘I want you folks to come to my house and eat strawberries and cherries and all’
hias close ictas.
hayas-ɬúsh íktʰa-s. 
‘sorts of good things.’
Hias warm illahee okoke sun pe conaway ictas chaco pilpil, wake siah.
hayas-wám-ílihi  úkuk sán pi kánawi íktʰa-s cháku-pílpil,  wík-sáyá.
‘It’s hot weather today and everything is getting ripe, just about.’
Wawa mesike papa pe mama nika hias ticky nanich mesika.
wáwa msayka pápá pi mámá nayka hayas-tíki nánich msayka.
‘Tell your dad and mom I’d love to see you folks.’
Nika hias sick tumtum halo tenas tillicum copa house.
nayka hayas-sík-tə́mtəm h(e)ílu tənəs-tílixam kʰupa háws.
‘I’m very sad there are no kids in the house.’
So hiack chaco nanich nika pe mesika grandmother.
so  (h)áyáq cháku nánich nayka pi msayka grandmother.
‘So come visit me and your grandmother soon.’
Nika tumtum hiack ticky close nanich.
nayka tə́mtəm (h)áyáq tíki ɬúsh-nánich. 
‘My heart wants to have a good look (at you) soon.’
Quansum nika midlight
kwánsəm nayka míɬayt 
hayas-ɬúsh úl cracking snap, ‘Dearest Old  Cracking Snap,’ is English-language letter-writing style and spoken slang. In regular old Chinuk Wawa, calling a kid “old” is weird. (James Dement was presumably a child if he needed to go talk to his mom & dad.) The Jargon just doesn’t do much in the way of improvising metaphors at the will of a single member of the speech community.
nayka tíki  msayka cháku ‘I want you folks to come (here)’ lacks the normal Irrealis subordinate-clause marker pus. This syntax is typical of Anglophone Settlers, due to their mother tongue’s way of phrasing things.
strawberries  pi chéris* — There’s never been a widely agreed-on word for ‘strawberries’ in Jargon, I think, although it’s a native plant here. Some version of the English word ‘cherries’, on the other hand, is consistently found.
kánawi hayas-ɬúsh íktʰa-s  ‘all sorts of good things’, and a further occurrence in a following sentence, is typically Anglophone Settler style, in using íktʰa-s as if it meant ‘thing-s’, whereas normal Chinuk Wawa narrows the meaning of this word a bit, to ‘belongings, property, clothing, jewelry’.
chaku-pílpil,  ‘getting ripe’ is the seemingly intended meaning. But the literal meaning here is ‘getting bloody’! Winston surely meant chaku-píl ‘getting red’ or maybe chaku-páya, the usual established phrase for ‘getting ripe’. He might have been a bit rusty at Chinuk Wawa, though it was still much in use in his area in the early 1890s. This was about a year before his death, so maybe his brain wasn’t what it once was?
so  ‘so’ is a tiny but tantalizing find. This same conjunction from English is documented in the speech of nearby Grand Ronde Indians born about the time of the letter. I don’t know of it in CW anyplace else.
nayka tə́mtəm (h)áyáq tíki ɬúsh-nánich.  ‘My heart wants to have a good look (at you) soon.’ That’s the literal translation of what Winston writes here. But this doesn’t sound like your average rather macho pioneer Settler male, so maybe he was aiming for ‘I’m thinking [that I] want to have a good look (at you) soon.’ Note his highly fluent placement of the adverb ‘quickly / soon’ before the verb it modifies.
kwánsəm nayka míɬayt  ‘I remain’ is nothing but Anglophone letter-writing style. In actual spoken Jargon, I wager it’d be exceedingly rare to find someone intending to say (aloud) ‘I stay James Winston.’ nayka míɬayt James would normally be taken as ‘I have James’ (!) or possibly ‘I’m staying (at) James(‘s house)’.