The Dutchess County Fair — the 169th edition of which takes place this month — is an event in the fullest sense of the word. Upwards of half a million visitors are expected to pass through the fairground gates to take the measure of 1,400-plus farm animals, check out everything from knitting and sewing demos to diving dogs and racing pigs, get wonderfully woozy on the midway rides, and eat their fill of fried dough and the freshest milkshakes this side of a dairy farm. The grandstand lineup includes country crooners Eric Paslay and Randy Houser (Aug. 20), and local favorites the Felice Brothers with Simone Felice (Aug. 22). Aug. 19-24 from 10 a.m.-10 p.m. $15, $10 seniors, under 12 free. Dutchess County Fairgrounds. Rte. 9, Rhinebeck, 845-876-4000.
Northern Dutchess County is abuzz with arts activity as Bard SummerScape — the seven-week festival of music, dance, film, cabaret, and other cultural doings — continues; highlights include the first U.S. staging in 100 years of von Weber’s opera Euryanthe (Aug. 1-2). In addition, the Bard Music Festival offers 12 concerts — along with panel discussions, lectures, and other events — which examine the work of 19th-century Austrian composer Franz Schubert (Aug. 8-17). And the elaborate mirrored Spiegeltent heats up late night, as cabaret host Justin Vivian Bond welcomes performance artist/singer Joey Arias (Aug. 2) and Amanda Palmer, former lead singer of the Dresden Dolls (Aug. 15), among other performers. Festivals run through Aug. 17. Call or visit Web site for complete schedule and ticket information. Bard College campus, Annandale-on-Hudson, 845-758-7900. www.fishercenter.bard.edu/summerscape
Bring out the cake and candles: Shadowland Theatre celebrates its 30-year anniversary this season with a recently completed building restoration and an expanded lineup of seven productions, two of which are on the boards this month. Artistic director Brendan Burke directs Unnecessary Farce, a comedy about a pair of rookie cops, a pretty accountant, and an undercover sting operation that goes hilariously awry (through Aug. 3). Toe-tapping country-western tunes fill the rafters when Honky-Tonk Highway — a musical about the reunion of a group of estranged band members — rolls in (Aug. 8-Sept. 7). Thurs.-Sat. 8 p.m., Sun. 2 p.m. $30 evenings; $25 matinees. 157 Canal St., Ellenville, 845-647-5511. www.shadowlandtheatre.org
As if it isn’t hot enough, the Belleayre Music Festival — an eight-week celebration of everything from blues to opera — heats things up even more this month. A fest within a fest, the five-show Catskill Mountain Jazz Series begins with a cool tribute to guitarist/composer Django Reinhardt (Aug. 1), but performances of Mexican (Aug. 7), Afro-Cuban (Aug. 8), and Brazilian bossa nova and tango music (Aug. 9) should send the mercury through the roof. Other headliners include actor/singer — and two-time Tony winner — Norbert Leo Butz (Aug. 16) and former SNL funnyman Colin Quinn (Aug. 23); shows continue through Aug. 30. Call or visit Web site for exact schedule, times, and ticket information. Belleayre Mountain Ski Center. Rte. 28, Highmount, 800-942-6904, ext. 1344.
So-called “outsider art” — that is, works created by self-taught artists who never attended art school — is the theme of the summer show at the Frances Lehman Loeb Art Center. Faces and Figures of Outsider Art includes paintings, drawings, sculptures, photos, and other items executed by more than 30 relatively unknown artists. The pieces focus on the human form — especially the face — and are unified in their unselfconscious style and emotional expression. Tues., Wed., Fri., Sat. 10 a.m.-5 p.m., Thurs. 10 a.m.-9 p.m., Sun. 1-5 p.m. through Aug. 31. Vassar College campus, 124 Raymond Ave., Poughkeepsie, 845-437-5632. http://fllac.vassar.edu