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Written by Nathaniel’s father four months after his son’s return from the Pacific coast: "….Your Brother Nathanl. sets of this week for a nother taste of the Origon, perhaps he has left some darling Squaw behind. I hope you will have a friendly parting and hereafter cordial meeting. You must do all you can to encourage him as I have done all I could to the contrary, but to no affect. Perhaps a veriety may be somewhat [accelliating?]. However, there is no one can charge him with indolence or want of enterprise. I hope he will have better luck in future, It is a very long night that has no day break. You give me a most splendid account of Jacob’s day dreams. I hope he may awake and find them realities. I would thank you to forward all the information concerning him you receive. For though he has been an exentric child he is still my son and your Brother. Do not forget to send all the assistance to Nathnl. in your power for I think his abilities will enable him hereafter to look up with prominence in society. I am sorry I was obliged to draw upon you so soon for that little sum you took from here but your Brother’s imperious necessities compelled me. I hope it has not deranged any of your speculations. Tell me as often and as much of yours and Leonard’s circumstances as is consistent with your business and pleasure; Write me a particular account of your losses and gains this troublesome year past. Keep up a cheerful heart, running the Christian race steadfast and unmovable…Your Brother Nathl. will tell you how much I grumble about our present Tennant; he has been very quiet since he learnt that Nat. was likely to return and I begin to think that I carry about as many guns as himself…" Dr. Jacob Wyeth, Jr., the black sheep of the family, decided, after returning from the expedition, to venture back into the frontier country, at least as far Illinois, where he intended to settle and open a medical practice. Begging his brothers for more financial support – his family had already put him through college – he swore that he would give up his alcoholic and spendthrift ways. He did go on to practice medicine in Galena for some years, but died young, years before his father and three brothers. Meanwhile, Nathaniel was off again to Oregon, and though his father tried to dissuade him, he was quietly proud of his son’s accomplishments and entrepreneurial spirit –and Nathaniel’s new-found reputation in Boston as a tough frontiersman, which served at least to intimidate one obstreperous Wyeth tenant in bucolic Cambridge. Nathaniel did indeed make another trip to Oregon in 1834, eventually returning safe and sound but with no greater profits than before. Eventually, he gave up on his dreams of Pacific wealth and went on to make a fortune in the far less romantic business of ice-making in New England.

Additional note on Letters of Nathaniel Wyeth’s First Oregon Trail Expedition

Nathaniel Wyeth led the first "emigrant party" to cross the Plains from Missouri to Oregon from May to October 1832. It was a hazardous overland journey, marked by privation, Indian attacks and personal conflicts in wild country previously known only to rugged Mountain Men and fur trappers. But Wyeth, an Eastern "tenderfoot" entrepreneur, who set out with twenty recruits, including his younger brother Jacob Jr., a neer-do-well Doctor, and 17 year-old cousin John, remained determined to reach the Columbia River, dreaming of wealth in the fur trade which had made John Jacob Astor the richest man in America.

These letters are taken from the unpublished papers of Nathaniel's brother Charles, a Baltimore merchant who, together with his brother Leonard in New York, helped bankroll the expedition. They reveal the undocumented conflicts within the Wyeth family which surrounded the famous expedition, including opposition to the venture by their father, Jacob Sr., a Massachusetts hotel owner; and the "desertion", midway, by the alcoholic Jacob Jr. and teenaged John, both of whom turned back after a battle with Indians in present-day Idaho.

One letter, written by Nathaniel after had reached Fort Vancouver alone, is a philatelic as well as historic rarity, being carried across the plains by agents of the Hudson's Bay Company. Two are written by Nathaniel's father and two others by John Wyeth's father, a semi-literate sea captain whose direct descendants were the famed artists Andrew and Jamie Wyeth. These letters illuminate the conflicts between Jacob Jr. and John after they had abandoned Nathaniel, significant because John, returning to Boston, published a ghost-written critical account of the journey which has become a rare classic of Oregon Trail literature.