In a report by The Examiner News, former North Castle Town Supervisor Michael Schiliro said, "When I moved here in 1999, there were about 2-4 restaurants in the Armonk Hamlet. Today, there are about 16-19, but 1-2 more are being added." That count matters more than it sounds like it should: the Art Show's 2026 weekend followed a month-long downtown program that only works if a downtown has enough separate stops to walk between.
The Armonk Outdoor Art Show returned to Community Park on September 26 and 27 for its 64th year, drawing roughly 160 juried artists chosen from a record pool of nearly 700 applicants, up from the previous record of 640 the year before. That part of the story was straightforward: a big, well-regarded show got a little bigger. The more interesting part was what had been quietly running through downtown storefronts since August 26, in the month leading up to the show.
The Trail You've Already Walked Through
Since late August, twenty original tabletop-sized sculptures created by Art Show artists had been displayed inside businesses across downtown Armonk as part of a program called Armonk Has Heart. Presented by the Art Show in partnership with the Armonk Chamber of Commerce and the Town of North Castle, it was designed to turn ordinary stops on Main Street into an informal, walkable gallery during the month leading up to the show. At the end of the program, the pieces were scheduled to be auctioned online, with proceeds going to the North Castle Public Library.
The 2026 format was a deliberate change from the previous year's. The inaugural 2025 version placed twelve large fiberglass hearts, each three feet wide and four feet tall, on pedestals around town, the kind of piece you'd notice from across a parking lot. One of them, painted by artist Stephen Anglim and installed near Wampus Brook Park, had been recognized by kids who'd seen his other work at the show itself. In 2026, the sculptures were smaller and moved indoors, tabletop-sized pieces tucked into storefronts, restaurants, offices, and gathering spaces rather than standing on the sidewalk. Smaller and easier to miss unless visitors already knew to look, which was the point: the format rewarded people who were already in these places for other reasons, picking up a coffee or a birthday cake, not people driving in for the show.
Why the Show Left Main Street in the First Place
It's worth knowing that the Art Show didn't start at Community Park. The first show in 1961 was held on the lawn of the Armonk Methodist Church, right on Main Street. As it grew, it moved to the North Castle Library's parking lot, then to the American Legion Field in front of Town Hall, and finally settled at its current home in Community Park in 1997. Each move solved a space problem and created a new one: the show got room to grow, but the visitors who used to wander past the church, the library, and the shops along the way stopped doing that once the whole event sat on a business park lot on the edge of town.
That was the gap Armonk Has Heart was built to close. It wasn't trying to move the show back downtown. It was meant to give show weekend a reason to touch downtown again, one storefront at a time, during the month before the gates at Community Park opened.
What Main Street Had to Become First
A trail like that only works if downtown has enough stops to make wandering worthwhile, and that's a fairly recent development. Schiliro's count of 2-4 restaurants in 1999 describes a Main Street that couldn't have supported a program like this. The 16-19 restaurants operating today are a different story entirely.
Some of what filled in that gap:
- Restaurant North, a four-time James Beard nominee run by Stephen Mancini and Danny Meyer alums Ralph Rubino and executive chef John Poiarkoff, serving locally sourced American fare right on Main Street.
- Moderne Barn, opened by the Livanos family in 2010 at 430 Bedford Road, now recognized as one of Westchester's premier celebration restaurants.
- Zero Otto Nove, an Armonk outpost of the Arthur Avenue original, with homemade pasta and a wood-burning brick oven turning out Neapolitan classics.
- Gavi, Casa Tequila, Amore, and Fortina, rounding out a stretch of Main Street where Italian, Mexican, and pizza-focused rooms now sit within a few doors of each other.
- Armonk Country Kitchen at 397 Main Street, the kind of soup-and-sandwich spot that doesn't need a website because its regulars already know where it is.
The retail side tells a similar story on a longer timeline. Hickory & Tweed has anchored Main Street since 1961, the same year the Art Show held its first show a few blocks away. Sugar Hi, the candy and bakery shop opened in 2017 by twin sisters Hillary Assael and Elissa Weinhoff, has grown enough to open a second location in Boca Raton this year while keeping its original Armonk storefront as home base. Make Believe Books, which opened in 2022, brought a bookstore back to a downtown that hadn't had one in a while, with owner Laura June Topolsky's flower-print wallpaper standing out against the more traditional shopfronts around it.
None of this happened because of the Art Show. But it's the reason the Has Heart trail can exist in its current form. A month-long scavenger hunt through downtown businesses needs a downtown with enough businesses to scavenge through, and Armonk only recently became that.
The Weekend Itself
The show had been scheduled to run from 10am to 5pm both days at Community Park, 205 Business Park Drive, rain or shine, with food trucks and children's activities alongside roughly 160 artists showing paintings, sculpture, photography, jewelry, ceramics, and mixed media. Managing Director Nancy Rosner and Artist Liaison Liz Green oversaw a show named Armonk's 2026 Organization of the Year, with proclamations from New York State Assemblyman Chris Burdick, Westchester County Legislator Margaret Cunzio, County Executive Ken Jenkins, and Congressman Mike Lawler recognizing more than six decades of the same work.
The show is run with the support of over 300 volunteers, and proceeds benefit the Friends of the North Castle Public Library, funding programs, upgrades, and the Armonk Players theater group. The Has Heart auction had been scheduled to close at the end of the weekend, with its proceeds designated for the same library.
For a quieter break during show weekend, visitors could have headed to Wampus Brook Park in the middle of downtown, with a gazebo bandstand and a brick memorial wall along the brook, close enough to walk to from Main Street without getting back in the car. Wampus Pond, a 38-acre natural pond nearby, offers fishing and rowboating through the fall before it turns into an ice skating spot in winter. For something with more tree cover, the Betsy Sluder Nature Preserve off Old Route 22 has an easy 1.5-mile loop, shaded and dog-friendly, about a 70-acre stretch that stays quiet even on a busy show weekend.
The sculptures displayed on counters and shelves around town had been scheduled to remain there through show weekend. The auction had been set to close at the end of the weekend, after which the pieces would go home with whoever bid on them, and Main Street would return to being just Main Street until next August.
If you walked Main Street during the program and spotted any of the twenty, Jessica Cunningham would love to hear which one was your favorite.
