Holidays in Winchester

Holidays at Home in Winchester

With COVID-19 procedures and precautions changing every day, it can be hard to keep up with Holiday events in Winchester! Where can you find events and activities happening and stay up to date with what’s been canceled? We have done the hard work for you! Below we have collected information on holiday events happening in Winchester and virtual events to help fill your holiday season with plenty of cheer!

Local Events

WINdependant Weekend
Put your money where your heart is this holiday season! Support local businesses in Winchester and start a new tradition of shopping local and keeping close to home! Now more than ever local businesses need your support. Shop in person, online, or buy a gift card this holiday season during the Windependent! Weekend in Winchester, November 27th through 29th.

Winter Wonderland in WinchesterWalking in a Winter Wonderland
Walking in a Winter Wonderland will take place from November 27th to January 3rd at Clearbrook Park in Winchester. This event invites you to walk through fantastic light displays and enjoy the music of the season. Clearbrook Park’s annual light show is a tradition sure to create lasting memories!

This year the Old Town Winchester Holiday Parade will be replaced by a new holiday light show. Holiday Lane will feature beautiful light designs, characters, and holiday decorations for the entire family to enjoy the comfort of their car! Holiday Lane will be available to drive through from November 30th to December 20th at in Jim Barnett Park.

Holly Jolly Celebration
Come spend time in Old Town this holiday season during the Holly Jolly Celebration on December 12th! Enjoy caroling and holiday activities, Holly Jolly Market, Santa’s Headquarters, free horse-drawn holiday wagon rides, specials at shops and restaurants, and more!

Virtual Events:

Many of America’s favorite Holiday Events are still happening this year for everyone to enjoy from home!

Macys Thanksgiving ParadeMacy’s Thanksgiving Day Parade
The Annual Macy’s Thanksgiving Day Parade will be converted to a made-for-TV spectacle, featuring the larger-than-life balloons, over-the-top floats, and big-name performers! You can watch the parade as always on NBC on Thursday, November 26th from 9 am to noon. Or, watch the live stream!

Rockefeller Center Christmas Tree Lighting
Enjoy the Rockefeller Center Christmas Tree Lighting on December 2nd with a live national broadcast hosted by NBC to officially mark the start of the Christmas season!

National Christmas Tree Lighting Ceremony
Washington D.C’s 98th National Christmas Tree Lighting Ceremony and holiday performances will take place on December 3rd on

Ball Drop on New Years EveNew Year’s Eve Ball Drop in Time Square
The Annual New Year’s Eve Ball Drop in Time Square will also occur virtually this year. You can still countdown the ball drop and pop some champagne in the comfort (and warmth!) of your own home! The event will feature the iconic ball drop countdown, as well as performances and a recap of the year’s events broadcast on television and live stream.

Whether you decide to celebrate your holidays virtually this year or find a way to visit family and friends, be sure to stay safe this Holiday season!