Holiday On Main 2019

Quick Overview

Holiday on Main Street is an annual Downtown Middletown event which begins the day after Thanksgiving and continues Saturday, November 30th, Saturday, December 7th, and Saturday, December 14th. 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!


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

Santa’s Mailbox

SANTA’S MAILBOX will be in front of Middlesex Chamber from Monday, November 18 to Friday, December 13! 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!

In the Event of Inclement Weather

Inclement weather postponement or cancellations will be posted on
In the Event of Inclement Weather


Mistletoe Title Sponsor

Jinglebell Sponsors

Holly Sponsors

Reindeer Sponsors

Elf Sponsors