MUSIC: Judy Collins @ Barrington Stage Company’s Mainstage @ Pittsfield. Sweet Judy Blue Eyes. The Grammy Award-winning singer-songwriter runs the gamut from her early folk music career to her more recent cabaret offerings. 7pm. $40, $48; VIP $70 (includes reception)
FAIR: Washington County Fair @ Washington County Fairgrounds, Greenwich. It’s opening day at the fair with music by the Smokey Greene Band (6 & 8pm) and a demolition derby (6pm), as well as magic shows, pig racing and all the usual fair doings. Gates open at 5pm. $10, which includes parking, admission and all attractions and entetainment (but not the midway rides).
MUSIC: Olivia Quillio @ Valentine’s Music Hall, Albany. WEXT-FM’s Laura Glazer & her “Hello Pretty City” show presents the barefoot, ukulele-strummin’ birthday girl Ms. Quillio, as well as Viking Moses, Mother McKenzie and Joey DeMarco. 8pm. $5.
THEATER/READINGS: “Richard Wilbur: A Celebration” @ the Colonial Theatre, Pittsfield. A very special tribute to the poet laureate, translator and lyricist as he celebrates his 90th birthday, featuring selections of his work in drama, musical theater and poetry. 2pm.
THEATER/COMEDY: Theatresports Tournament @ the Spectrum Playhouse, Lee. The Royal Berkshire Improv Troupe faces off against the Mop & Bucket Co. for a one-night-only battle of the improv comedy groups. Among the celebrity judges will be Debra Jo Rupp, perhaps best known as mom Kitrty Forman on the long-running sitcom “That ’70s Show.” The battle is a fundraiser for the WAM Theatre. 7:30pm. $15.
MUSIC: The Nancy Walker Trio @ Veteran’s Memorial Field, Athol. Country, folk and more…7pm. FREE.
FILM: “The Tree of Wooden Clogs” @ Clark Art Institute, Williamstown. Ermanno Olmi’s epic 1978 saga follows four peasant families who live and work on an Italian estate. 2pm. Free with museum admission.
MUSIC: Stella & the Hudson Valley Hot Club @ Club Helsinki, Hudson. Gypsy jazz ‘n’ swing quartet. 8pm. FREE.
MUSIC: Casey Ahner @ Elks Club lawn, Albany. The Pine Hills Monday Summer Concert Series Continues… 7pm. FREE.