There is no place like Winchester for the Holidays!

Downtown Winchester is gearing up for another memorable holiday season. We’re encouraging people to experience the holiday season downtown by exploring the city’s unique shops and restaurants, and enjoying the sights, sounds and tastes of our neighborhood.

So you don’t miss the holiday happenings in downtown Winchester this season, Winchester First has announced a schedule of events and activities planned throughout downtown.

  • Halloween MAIN-ia: Trick or Treat on Main Street will be 6-8 p.m on Friday Oct. 31. Main Street will be closed from Lexington Avenue to Washington Street  to ensure safety. Any business not located downtown, or within the shutdown area is invited to participate. Simply bring a table and candy and find an open spot on the sidewalk to set up.  Prior to trick or treating children and their parents are invited to the Bluegrass Heritage Museum for  Spooktacular Story-time with the Clark County Public Library from 5-6 (story every 15 minutes).  Throughout the evening, the Leeds Center for the Arts will have its concessions open and will be offering free tours of the theater.
  • Mystery Dinner Theater: The Cairn Coffee House will be hosting a Mystery Dinner Theater ($25) on the evenings of Oct. 27-30.  Visit for tickets and more information.

• The Downtown Holiday Open House will be Nov. 6-9, and participating businesses will offer sales and early discounts – they will also have special extended hours. Be sure to check out the Downtown Winchester Facebook page to vote on your favorite holiday window displays! And don’t forget to enter to win The Great Gift Giveaway – an entire window of great gifts from downtown retailers.

• Make and Take Card Craft at 18 W. Lex Ave. Artisan Gifts and Gallery during Holiday Open House Saturday, Nov. 7.

  • All Things Bluegrass on Nov. 6 at the Bluegrass Heritage Museum. A kick off celebration for the Good Giving Challenge. Music, refreshments, door prizes. Begins at 6:30 pm.
  • Shop Small Saturday, created by American Express, will be Nov. 29. People are encouraged to shop at small and local businesses on this day.

• The Winchester Christmas Parade will be at 6 p.m. Dec. 6 on Main Street. The theme for the parade is “A Winchester Christmas.” For a parade entry form, email [email protected]. Forms are also available at the Winchester First office in City Hall. (Rain date: Sunday, Dec. 7 at 2 p.m.)

  • The Polar Express: Children are invited to don their favorite holiday pajamas and visit Deb’s Depot during the Christmas Parade for complimentary hot chocolate and a reading of The Polar Express. The restaurant will be transformed into a train dining car for the occasion! Ticketing information available soon.
  • Story time with Mr. and Mrs. Klaus at the Bluegrass Heritage Museum on Dec. 13 2-4 p.m.
  • Bluegrass Heritage Museum will be resplendent with decorations, live music, and refreshments during its holiday open house Dec. 16.