Sept 6–8, 99 Moseman Rd, Yorktown Heights
Where else can you enjoy a watermelon-eating contest, merry-go-round, and baking competition all in one spot? This year, the 95th Annual Yorktown Grange Fair will focus on the interdependent relationship between community and local agriculture with the theme “Back to the Garden.” Guests can also indulge in food and drink, various contests, a tractor parade, fun carnival rides, and live entertainment.
Sept 13–15, Lyndhurst Mansion
At Fall Crafts at Lyndhurst, more than 300 artists, artisans, designers, and craftspeople from across the country showcase their incredible creations. Treasure seekers can spy everything from furniture and jewelry to pottery and paintings while enjoying gourmet food and concessions, hands-on demonstrations, and a host of kid-friendly activities.
Sept 26, Empire City Casino, Yonkers
Why hit every wing spot in Westchester when you can taste almost all of them in one place at Westchester Magazine’s annual Wingfest? With drinks, live music, and the best chicken wings around served by 20+ local restaurants each competing for the crown, the fest is a worthy stop for anyone with a penchant for food and fun.
Oct 4-6, Various Locations, New Rochelle, Pelham
Along with an Arts in Oktoberfest Gallery Hop, a classic-car show, behind-the-scenes tours of artists’ workshops, and a performance by Ajkun Ballet, the ArtsFest will also unveil a historic mural project bringing several renowned large-scale artists to the Queen City.
November (exact dates TBD), Various Locations
Local cinema buffs rejoice! The Yonkers Film Festival, fondly referred to as YoFi Fest, is a must-attend event for anyone with a soft spot for under-the-radar movies. Now celebrating its seventh year, YoFi specializes in shining a spotlight on local filmmakers by screening more than 150 full-length features, short films, documentaries, and other works.
Sept 20–Nov 30, Van Cortlandt Manor
With more than 7,000 illuminated jack-o’-lanterns overtaking the expansive grounds of Hastings on Hudson’s Van Cortlandt Manor in shapes ranging from incredible beasts to eye-popping structures, this popular outdoor event is the perfect opportunity to get into the spirit of the spooky season.
Sept 21 & 22, 205 Business Park Dr., Armonk
Peruse the wares of 185 juried artists — 35 new to the show — selling jewelry, paintings, crafts, photography, prints, and a host of other creative works at this two-day event, which includes childrens activities, food, and free parking.
Sept 11–15, ArtsWestchester Gallery, White Plains
Free and open to the public, ArtsWestchester’s 2019 Jazz Fest has become one of the county’s signature musical events. Celebrating its eighth year lighting up the section of Mamaroneck Avenue in front ArtsWestchester’s White Plains headquarters, this year’s fest boasts an impressive lineup of jazz greats, including Joel Ross, Melissa Aldana, Emmet Cohen, and many others.