Main •
Didi Conn as Stacy Jones, the kindhearted station master and aunt to Matt and Dan •
Brian O'Connor as Horace Schemer, the proprietor of the station's arcade •
Ringo Starr as Mr. Conductor (season 1, Christmas special), a 20-centimetre tall conductor with a magic whistle that helps him teleport away •
George Carlin as Mr. Conductor (seasons 2–3, family specials), the first Mr. Conductor's cousin •
Leonard Jackson as Henry "Harry" Cupper (season 1, Christmas special, family special 3), an engineer and grandfather of Tanya and Kara •
Nicole Leach as Tanya Cupper (main, season 1, Christmas special; guest, season 2), Harry's granddaughter and Kara's cousin •
Jason Woliner as Matthew "Matt" Jones (main, season 1, Christmas special; guest, season 2), Stacy's nephew who visits the station •
Tom Jackson as Billy Twofeathers (seasons 2–3, Family Specials), the engineer who replaced Harry after he left and Kit's uncle •
Erica Luttrell as Kara Cupper (seasons 2–3, Family Specials), Harry's granddaughter and Tanya's cousin •
Ari Magder as Daniel "Dan" Jones (seasons 2–3, Family Specials), Stacy's nephew and Matt's cousin • Danielle Marcot – Becky (recurring, season 2; main, season 3, Family Specials), a local girl who is friends with Dan and Kara
Recurring • Jerome Dempsey as Osgood Bob Flopdinger, the mayor of the town of Shining Time • Mart Hulswit as J.B. King,
Esq., the superintendent of the Indian Valley Railroad •
Bobo Lewis as Midge Smoot, the town gossip • Jonathan Shapiro as Schemee (seasons 2–3, Family Specials), Schemer's nephew •
Gerard Parkes as Barton Winslow (seasons 2–3), the proprietor of the town's general store •
Barbara Hamilton as Ginny Johnson (seasons 2–3, Family Specials), a farmer • Aurelio Padrón as Felix Perez (seasons 2–3, Family Specials), a bus driver • Bucky Hill as Kit Twofeathers (Family Specials), Billy's nephew
Notable guest stars •
Ardon Bess as Tucker Cooper, Harry's cousin (Tis a Gift") •
Lloyd Bridges as
Mr. Nicholas (Tis a Gift") •
Rachel Miner as Vickie (Tis a Gift") •
Ed Begley Jr. as Ned Kincaid and his great-grandson ("Once Upon a Time") •
Jack Klugman as Max Okowsky ("Second Chances") •
Teri Garr as Sister Conductor ("One of the Family") •
Jeannette Charles as
the Queen ("Queen for a Day")
The Jukebox Band •
Jonathan Freeman as Tito Swing, the pianist • Olga Marin as Didi, the drummer •
Wayne White (1989) and Alan Semok (1990–95) as Tex, a guitarist • Craig Marin as Rex, a guitarist •
Peter Baird (1989–95), Alan Semok (1989), and Kenny Miele (1990–95) puppeteering Grace, the bass guitarist • Emily Bindinger as the singing voice of Didi • Rory Dodd as the singing voice of Tex and Rex •
Vaneese Thomas as the speaking voice (1989) and singing voice (1989–95) of Grace •
Beverly Glenn-Copeland as the speaking voice (1990–95) of Grace The instrumentation of the songs was performed and produced by Steve Horelick, who also arranged the vocals. The music was arranged by Larry Wolf. ==Segments==