Holiday on Main Street is an annual Downtown Middletown event which begins the day after Thanksgiving and continues Saturday, November 25th, Saturday, December 2rd, Saturday, December 9th and Saturday, December 16th. This event has developed family holiday traditions and drawn young and old to celebrate the holiday season in Downtown Middletown for over 30 years. With a variety of entertainment every week ranging from free horse and wagon rides to Santa Claus, there is certainly something for everyone. Holiday on Main Street is a great opportunity to enjoy the season with friends and family. Come, join the fun!

SANTA’S MAILBOX will be in front of Middlesex Chamber from Monday, November 20 to Friday, December 8!  Write your letters to Santa and bring them to Holiday On Main Street to mail to Santa!  Please be sure the child’s name and address are on the letter, so Santa can respond!

PARKING is FREE in CITY PARKING LOTS during Holiday On Main Street!  Main Street parking will be monitored.

Inclement weather postponement or cancellations will be posted on

Enjoy the video of last year’s final tree lighting at Eli Cannon’s, quite a crowd this year!

Holiday On Main 2015 Tree Lighting at Eli Cannon’s Tap Room from Middlesex Chamber on Vimeo.