Here Are 8 Must-Do Events in Westchester This Year

From food trucks, to music, and an outdoor art show, these are 2018’s standout events.


Lyndhurst Flower Show

Florists from across the Lower Hudson Valley display beautiful arrangements at Lyndhurst Mansion’s second annual Spring Blossoms flower show. The sprawling, 67-acre park in Tarrytown hosts the three-day show April 6 to 8; visitors can partake in guided tours from 10 a.m. to 4 p.m. or experience the floral arrangements themselves. The show will host a variety of local florists, including Blossom Flower Shops, Forever in Bloom, Joseph Richards Florals, Seasons on the Hudson, and the Garden Club of Irvington.

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Rye Food-Truck Festival

Kick off summer with this celebration of mobile food — where else can you find wood-fired pizza, gyros, lobster rolls, homemade ice cream, and rousing live music all in one place? The Rye Recreation Center hosts its third annual Food-Truck Festival, attracting 12-plus food trucks from across New York and Connecticut. Previous participants have included Little Taste of Peru, LobsterCraft, Melt Mobile, Boxcar Cantina, Three Little Pigs BBQ of Westchester, and Walter’s Hot Dogs. The festival also has a kid’s zone and beer tent.


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Photo by Lynda Shenkman Curtis

Pleasantville Music Festival

The 14th anniversary of the Pleasantville Music Festival features both national and local rock acts, myriad food vendors, and drinks, including a beer-and-wine garden, and activities to foster a positive vibe among festivalgoers. Blues Traveler, Suzanne Vega, The Revivalists, and Guster have been featured rock acts in previous years. The festival also encourages a zero-waste policy enforced through waste collection centers set up throughout the festival grounds. Taking place at Parkway Field off Marble Avenue, the event is presented by Westchester Medical Center and sponsored by 107.1 The Peak.



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Armonk Outdoor Art Show

Close to 200 juried artists appear at the 2018 edition (and 57th annual) Armonk Outdoor Art Show. Hosted in North Castle Community Park on a September weekend, the yearly exhibition showcases art from across the country and throughout the world. Each artist has their own booth, featuring art that ranges from oil and watercolor painting to printmaking, photography, and jewelry.  Other amenities include kids’ activities, a food court, and free parking and shuttle service.


White Plains Jazz Fest 

The White Plains Jazz Fest returns for its seventh annual celebration. The five-day festival hosts a variety of local jazz performers at several locations, including ArtsWestchester and White Plains Performing Arts Center. The event climaxes on the final day with a free outdoor Jazz and Food Festival on Mamaroneck Avenue. Performances encapsulate jazz in all its worldly forms, including American Jazz, Afro-Cuban Jazz, and Jazz Fusion. 



Photo by Heather Sommer

Apple Picking at Wilkens Fruit & Fir Farm •

Leaves aren’t the only colorful objects falling from trees this fall. Just ask the staff at Wilkens Fruit & Fir Farm. The Yorktown Heights farm, in its 102nd year of operation, offers apple, peach, and pumpkin picking daily from late August through mid-December. Guests can also visit the bakery (the apple-cider donuts are renowned), farm market, or country market, featuring gifts and local crafts. Once Thanksgiving passes, Wilkens also offers “choose-and-cut” Christmas trees from a variety of firs grown on the farm. Outhouse Orchards in North Salem and Stuart’s Fruit Farm in Granite Springs are other delicious apple-picking options.



Bedford Antiques Show at Historical Hall

This annual boutique show provides a breath of excitement to the quaint village green of Bedford, featuring approximately 20 dealers inside an 1806 historic landmark. These vendors specialize in everything from antique furniture, textiles and jewelry to fine art, china, and decorative accessories. The show attracts dealers from New York, Massachusetts, and Connecticut, ensuring a fresh, new mix of items each year.


Holiday Parade & Tree-Lighting Ceremony at Cross County Shopping Center

The Cross County Shopping Center in Yonkers hosts the first county tree-lighting event of the holiday season. The lighting of the 40-foot Christmas tree is only part of the annual tradition however: the night also features live music and a Holiday Spectacular Parade. Past participants have included Girl Scout troops, Irish step dancers, and local schools — and Santa Claus makes an appearance of course!

Our Best of Westchester Party is July 24!

Our Westchester Home Design Awards event is June 26!

Our Wine & Food Festival returns June 4-9!

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

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