She was associated with the early 1960s Greenwich Village folk music scene, particularly with Fred Neil, the Holy Modal Rounders, and Bob Dylan.

She played alongside big names of the time, including Bob Dylan (who occasionally backed her on harmonica),[7] Fred Neil, Richard Tucker, and Tim Hardin.

[11] Dalton moved to Colorado with husband Richard Tucker and daughter Abralyn (Abbe) and lived there for a while in the 1960s, in a small mining cabin in Summerville.

[8] Dalton was "not interested in playing the music industry's games in an era when musicians had little other choice," as bass player and producer Harvey Brooks noted.

[12] It's So Hard to Tell Who's Going to Love You the Best was re-released on Koch Records in 1997, in collaboration with New York-based radio DJ and Karen Dalton fan Nicholas Hill, and with liner notes by Peter Stampfel.

[13] The compilation tribute album, Remembering Mountains: Unheard Songs by Karen Dalton, was released in 2015 by folk label Tompkins Square.

The songs feature lyrics and poems Dalton wrote before her death, which were in the care of her friend, folk guitarist Peter Walker.

[5] In later years, Dalton lived in a mobile home located in a clearing off Eagle's Nest Road, outside the town of Hurley, near Woodstock.

[16] Friend Lacy J. Dalton helped send her to rehab in Texas in the early 1990s, a stay which lasted only a couple of days before she demanded to be taken back home to Woodstock.

[11] A documentary, Karen Dalton: In My Own Time, from filmmakers Richard Peete and Robert Yapkowitz, made its world premiere at Doc NYC in November 2020.

Sheri Linden in The Hollywood Reporter writes: "As it introduces a one-of-a-kind artist to the uninitiated and celebrates her for aficionados, above all it listens — and invites us to do the same.