In 1988, traversing synonyms in the Merriam-Webster Collegiate Dictionary, A. Ross Eckler found his way from TRUE to FALSE:

TRUE-JUST-FAIR-BEAUTIFUL-PRETTY-ARTFUL-ARTIFICIAL-SHAM-FALSE

He found his way back again by a different route:

FALSE-UNWISE-FOOLISH-SIMPLE-UNCONDITIONAL-ABSOLUTE-POSITIVE­-REAL-GENUINE-TRUE

He was using the dictionary’s ninth edition; see the article below for his conventions regarding qualifying synonyms. Two more examples:

BAD-POOR-MEAN-PENURIOUS-STINGY-CLOSE-SECRET-FURTIVE-SLY-CUNNING-CLEVER-GOOD

GOOD-CLEVER-CUNNING-SLY-FURTIVE-SECRET-TICKLISH-CRITICAL-ACUTE-SHARP-HARSH-ROUGH-INDELICATE-INDECOROUS-IMPROPER-INCORRECT-WRONG-SINFUL-WICKED-EVIL-BAD

LIGHT-BRIGHT-CLEVER-CUNNING-SLY-FURTIVE-SECRET-HIDDEN-OBSCURE-DARK

DARK-OBSCURE-VAGUE-VACANT-EMPTY-FOOLISH-SIMPLE-EASY-LIGHT

Somewhat related: Lewis Carroll invented word ladders, in which one transforms one word into another by changing one letter at a time:

COLD-CORD-WORD-WARD-WARM

Each intermediate step must itself be an English word. Donald Knuth once used a computer to find links among 5,757 common five-letter English words. 671 of these, he found, were not connected to any other word in the collection. These he dubbed “aloof” — and noted that ALOOF itself is such a word.

(A. Ross Eckler, “Websterian Synonym Chains,” Word Ways 21:2 [May 1988], 100-101.)