Happy Trails is based in Sac-Town, north of Shady Sands, and does most of its business with New Reno and on the road to Salt Lake City. They are competitors with the Crimson Caravan for trade. After several seasons of bad trading, and since the loss of contact with New Canaan in 2281, the company is in dire financial straits and is preparing to launch an expedition to New Canaan via Zion Canyon in order to reconnect with the Mormons there. The only viable route to Salt Lake City is through Zion Canyon via the Mormon missionary. They cannot take I-80 there due to the lack of NCR Rangers keeping the raiders at bay, and they cannot take the Oregon route because they would lose more in traveling expenses than they would make.
None of the members can be pickpocketed when the player character meets them at the northern passage.
Happy Trails can have one of two fates: they return to success and good fortune because the White Legs were driven out, or the Sorrows's evacuation allows the White Legs to keep Happy Trails out. The latter causes the company to go bankrupt.
↑Jed Masterson: "Hang on - ain't you the one that wiped out the Crimson Caravan's Vegas branch not too long ago? Ought to thank you for that - knocking McLafferty out of the running gives Happy Trails a market to expand into." (Jed Masterson's dialogue)
↑Jed Masterson: "Wait a minute, I recognize you. Yeah... you're Alice McLafferty's rising star, ain't you? You sure you want to be here? McLafferty's non-competes are pretty rigid." (Jed Masterson's dialogue)
↑The Courier: "Tell me about Happy Trails Caravan Company." Jed Masterson: "We're a smaller company out of Sac-Town, up in the northern part of the NCR. We run some business through New Reno, there on the "Little Loop." Had a nice run to Salt Lake City, too - but then we lost contact with New Canaan, and that went all to hell." (Jed Masterson's dialogue)
↑The Courier: "You don't know what happened to their mission?" Jed Masterson: "Nope - hence this caravan. If we don't make contact with the New Canaanites, Happy Trails might as well just shrivel up and die." (Jed Masterson's dialogue)
↑The Courier: "Why can't you get to Salt Lake City?" Jed Masterson: "Without New Canaan's mission in Zion, the only ways to Salt Lake City are down the old I-80 or up through Ogden. The highway's too risky - NCR's rangers are so busy here in the Mojave they don't have the manpower to keep the raiders off. Ogden's just too far - we'd lose more in travel expenses than we'd ever earn." (Jed Masterson's dialogue)
↑The Courier: "It sounds like Happy Trails isn't in the best financial shape." Jed Masterson: "[SUCCEEDED] You ain't wrong. Losing the Salt Lake City run really stung us. If we can't re-establish contact with this run, we'll be in real trouble." (Jed Masterson's dialogue)