Pound Ridge; townofpoundridge.com
Food trucks, music, and free popcorn for kids beginning at 5 p.m. on three summer Wednesdays (June 29, July 13, July 27) in the town park.
Every Monday (July 11–Aug 29) is movie night on the South Lawn (near Whole Foods). Family-friendly activities begin at 7 p.m., and the big screen comes to life at sunset.
Movies at sunset at Jack DeVito Field on three summer Fridays: June 24, July 22, Aug 26.
Be seated on the lawn in front of Bronxville High School, Wednesdays in July at 8 p.m., for standards from the Great American Songbook.
A plethora of live music opportunities are here, and the yearly not-to-miss event is the Pops & Patriots concert by Westchester Symphonic Winds, on July 2 at 4 p.m., in an open-air, fully covered theater.
Settle into Market Square and sing along to locally popular acts like The Mike Risko Band and Blame It on the Dog, every Wednesday, July 6–Aug 10, at 7 p.m.
Move to the music from a variety of Westchester- and Hudson Valley-based bands on Fridays in July (plus June 24 and Aug 5) at 7 p.m. at Senasqua Park.
This much-loved annual event — featuring both Billy Joel and Bruce Springsteen tribute bands, among others — kicks off on June 26 at 6 p.m. and continues most Sundays in July and August at Jack DeVito Field.
Summer 2022 is the summer of fun at Cross County Center with family-friendly and kid-centric concerts at 6:30 p.m. in June and July (June 29 & 30; July 13 & 28), with more planned for August (at press time).
New Rochelle; newrochellearts.org
This rousing, well-attended annual series takes place every Wednesday in July and August at Hudson Park at 7:30 p.m.
A full day of tunes and family fun is a sure thing at this much-anticipated, highly attended annual event — which has attracted thousands, along with such hot tickets as Blues Traveler, Soul Asylum, and Gin Blossoms — on Saturday, July 9, at Parkway Field.
Culture and community are celebrated throughout the clement months at these vibrant gatherings, which feature an afternoon of traditional food, crafts, music, and entertainment. Here is the June lineup (at press time): June 4: Asian; June 5: Albanian; June 26: African American
Related: Where to Catch an Outdoor Movie in Westchester County