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The following was submitted by the En Ka Society:
The En Ka Society’s annual Street Fair will be held on Friday and Saturday, May 15-16, 2026.
The En Ka Society is a non-profit charitable organization comprised of over 200 women volunteers dedicated to assisting the town of Winchester and its residents. The Society supports the Winchester community with monetary assistance in the form of grants as well as direct social service programs, including the En Ka Pantry, which provides food and personal care needs to individuals and families residing in Winchester
The Fair, which is a long-standing Winchester event dating back to 1935, is En Ka’s largest fundraiser. Proceeds from the Fair help support the En Ka Pantry as well as other social service programs and quarterly grants that help organizations and people of all ages in Winchester.
Over the last 25 years, En Ka has awarded grants to Winchester Public School programs, the Winchester Public Library, the Jenks Center, VNA hospice care, Winchester Got Lunch, Friends of Upper Mystic Lake, Winchester Community Music School, Wright-Locke Farm, and Mission of Deeds and many other public and non-profit organizations that serve the people of Winchester.
In addition to rides and games provided by Rockwell Amusements, the En Ka Street Fair has many beloved traditions, including the Baked Goods Table, the Jewelry Sale, the Book Tent, and Lobster Rolls, to name a few.
The En Ka Parade, another longstanding tradition, will be held Saturday morning, May 16, beginning at 9:15 a.m., with the route extending from Winchester High School down Main Street, around the Town Common, and ending at the Fire Station.
The theme of this year’s Fair is “Rock the Smock,” and Fair Co-Chairs Carey Sue Barney and Mary Scott hope the Winchester community has a rocking good time at this year’s Fair.
The Street Fair will be held in the Town Hall/Jenks parking lot on the following dates and times: Friday, May 15, from 4 to 10 p.m. and Saturday, May 16, from 10 a.m. to 9 p.m.
Advanced tickets will be available for sale at the Town Hall parking lot on Thursday, May 14, from 12 to 6 p.m. and Friday, May 15, from 8:30 a.m. to 3:30 p.m.
In addition, online tickets are available until 7:30 p.m. on Wednesday, May 13 at https://enkasociety.org/en-ka-fair/.
Street and parking lot closures
The Mt. Vernon Street side of the Jenks Parking Lot will be closed, excluding the spaces designed for the Jenks. The Jenks Parking Lot will be completely closed, as of May 12.
Skillings Road, from the entrance to the high school to the five-way intersection at Mt. Vernon and Washington, will be closed at 9 a.m. on Wednesday, May 13. Skillings Road, from the five-way intersection to the entrance of the high school, will be closed on Thursday, May 14 at 9 a.m.
Mt. Vernon Street will be closed, from the rotary to the five-way intersection, on Thursday, May 14 at 6 p.m.
