The Miss Winchester Beauty Pageant is a new addition to the Fall Winchester Wriggle to be held Saturday, Sept. 26 in downtown Winchester. 

Winchester Wriggle is a semiannual art experience guiding participants throughout Winchester’s Historic Downtown District; promoting fine art, musical talent, and cultural diversity.  At each business, you will enjoy a variety of specials, refreshments, art, music and more Wriggle around the entire Downtown District to catch it all. After the beauty pageant a Lip Sync Competition will be held at the amphitheater at 8 p.m.  Contact Lauren Martin at Winchester Main Street for additional information.

The pageant will be held at the Kiwanis Amphitheater on the side street by the Oldham Theater at 5 p.m. – 7 p.m. with registration beginning at 4 p.m.  To ensure social distancing no changing facilities will be available, you must come dressed.  Pageant attire.  You do not have to reside in Winchester to compete.

There will be seven categories:  Baby Miss - newborn to 18 months old; Wee Miss - 19 months to 3 years old; Tiny Miss - 4-5 years old; Petit Miss - 6-8 years old; Junior Miss- 9-12 years old; Teen Miss - 13-16 years old; and Miss Winchester – 17-24 years old.

Entry fee is $40 including photogenic, which should be brought to registration with child’s name and age on back of photo no larger than an 8 x 10.  There is a sibling discount if you have two or more children from the same family, the entry fee is $35.  Proceeds from the pageant will go towards college scholarships.

You may pick up entry forms at Belles and Beaus in downtown Winchester or email You can pay entry fee through Paypal at, check, money order, or cash.

Deadline for entry is Wednesday, Sept. 23, 2020.  Judges will be from out of town.

For additional information or entry form contact Yvonne Stewart at missmusicrow@gmail.c

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