Of choosing her collaborators, Collins explained "I knew Jonas and Chatham County Line would be a great fit with me.

The recording of the album took place in February 2019 at Echo Mountain Studios, a former church in Asheville, North Carolina where the artists were given three days of preparation and pre-recording time during which they picked the songs, a mixture of classics, covers and originals through sharing stories and exchanging experiences, something Collins described as "very much a part of the folk tradition.” Of the album's seasonal theme, Fjeld explained "I’m a winter guy — in my part of the world it's winter seven months of the year.

Writing for Americana UK, Jonathan Aird selects "The Blizzard" as the album's standout track, explaining that it is "one of her most stunningly effective songs" detailing "love, and consolation, and drinking and an eventual parting captured over a magical six minutes" and also praises Collins' cover of "River", writing that "it's hard to imagine anyone else but Judy Collins making such a fine version of a song whose original perfection makes it almost sacrosanct".

Aird additionally praises the "magical" re-recording of "Angels in the Snow", the "ethereal" cover of "Highwayman" and "Bury Me With My Guitar On" on which Chatham County Line "get to rip a little more as the song bounces along at a Bluegrass pelt".

[4] Similarly, Doug Heselgrave of No Depression described the album as a "new folk classic" featuring a "winning combination" of Collins, Fjeld and Chatham County Line.