Don't Miss: Ossining Village Fair Returns After 2-Year Hiatus

OSSINING, NY — The rain date is Sunday. Let's just get that out of the way before we talk about the Ossining Village Fair, which returns to Main Street this weekend with a lot of food, fun and friends.

The 40th Annual Ossining Village Fair, set for Saturday in a beautiful Hudson River town increasingly known for cultural foods, art, music, dance, and theater, is just the thing to help celebrate post-pandemic community bonds.

"Forty years and still going strong, the annual Village Fair is a tradition and one of the pillars of celebration here in Ossining,” said Dr. Gayle Marchica, President of the Greater Ossining Chamber of Commerce.

The free family-friendly event will officially kick off at 10 a.m. with a street dedication to Neil Woolf, the late owner of Bob’s Army and Navy store, who died at the beginning of the pandemic, in April 2020.

The Chamber of Commerce, Village of Ossining, and Historian Joyce Sharrock-Cole worked together on the dedication event. The Opening Ceremony will take place at the Main Street Stage at 10 a.m. featuring the Elks Club Flag Ceremony, National Anthem, and ribbon cutting.

What else can you expect?

• LIVE MUSIC & PERFORMANCES with three outdoor stages will be placed along the Fair route featuring a special selection of the area’s live music and dance acts. The performance areas curated by Greater Ossining’s own DJ Johnny G, Mike Risko Music, and School of Rock promise to bring hours of entertainment, fun, and community engagement.
• FOOD and BEER GARDEN featuring local food trucks, cultural cuisine, and of course, beer by Ossining’s own Sing-Sing Kill and Six Degrees or Less Breweries will be doing their thing. We also boast Ossining’s Wanna Empanada and Brothers Fish-n-Chips as well as our guest foodies Pizza Vitale and Wrappers Delight. In addition to artisan cuisine, fairgoers can visit local Downtown restaurants as well as partake in traditional fare including funnel cakes, fries, kettle corn, hot dogs and more.
• KIDS ZONE is of course, kid-friendly, sporting lots of activities, games, hoop shoot, face painting, and crafts all in one fun place. The area highlights anything related to “kids” including programming, information, non-profits, and businesses. Along with the fun, Ossining’s own Recreation Department and Youth Bureau will be on hand to provide information regarding summer employment and upcoming programming.
• CRAFTERS ROW will be set up on Main Street with some of the most talented artisans in the Hudson Valley and newly formed small businesses. Many of these entrepreneurs have been featured in Ossining’s Saturday Pop-UP Market. Their wares include photography, soy candles, culinary delights, and much more. Small businessS3 has been integral in getting the market up and running. Come and meet these ladies in person.
• VENDORS AND LOTS OF INFORMATION 100+to be exact... will be onsite for Fairgoers to engage and spend money! Businesses, non-profits, politicos,the school district, and organizations will be full of giveaways and information. You can interact at your leisure.

The fair's sponsors deserve a shout-out, including Gold sponsors Mark Seiden Real Estate Team, Open Door Family Medical, NY Presbyterian Hudson Valley Hospital, DJ Johnny G, Village of Ossining, Ossining Parks and Recreation, and Mike Risko Music; and Bronze sponsors including Hope’s Door, Coral Sea Pools, and PKF O’Connor Davies Accountants and Advisors.

The Chamber will have a special tent with LOVE OSSINING merch. Mugs, t-shirts, magnets, pens, and key chains will be available for purchase.