Citizen of the Year
Annually, the Chamber of Commerce honors one resident who has made a significant contribution through his or her work to the improvement of the business community or the overall quality of life in Winchester.  Citizens so honored include:

Arts in August

An annual collaboration between artists and local businesses which display artworks through the month of August. 

Concerts & Movies on the Common

En Ka Fair
Sponsored by the En Ka Society, the En Ka Fair is held during the third weekend of May.  A highlight of the fair is the Saturday morning parade.  The proceeds from the fair are redistributed back to the community through the En Ka Gifts program. 

Holiday Tree Lighting

Traditionally held on the first Thursday of December, this event includes a visit by Santa and carol singing. The Chamber of Commerce also sponsors special events on this day.

Town Day
Traditionally held on the first Saturday (and Friday) of June in the Town center, Town Day is popular event sponsored by the Winchester Town Day Committee.

Trivia Bee
Sponsored by the Winchester Foundation for Educational Excellence, this event is traditionally held in early February.  Proceeds are used for special projects or programs in the schools.

Winton Club Cabaret
A fund-raiser for Winchester Hospital, this show opens on the last Tuesday of January and runs through Saturday.  Auditions are open to the public.