Holiday On Main 2020

Quick Overview

During these uncertain times, we are looking to bring a little Magic to Middletown! As you may know, Holiday on Main Street is an annual event held in Downtown Middletown on the weekends from Thanksgiving to Christmas. Due to COVID-19, we have put our holiday thinking caps on and have come up with interactive, safe and socially distant events that will get the community excited and downtown to feel the holiday spirit. This series of events will be called, The Magic of Middletown!! The Magic of Middletown will begin with a virtual tree lighting which will be released on Friday, November 27 and will be followed by socially distant events on the follow Saturday’s: November 28, December 5 and December 12, which will feature popcorn and pretzels, pictures with Santa, holiday music, a pop-up vendor fair, a Spectacular Savings Saturday and a Tis the Season to Find a Gnome scavenger hunt at different locations throughout downtown. We will also have a Dashing through Downtown Holiday Parade on Friday, December 4 which will feature a decorated car parade that will travel around downtown Middletown to showcase our beautiful Main Street and the surrounding areas!


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 16 to Friday, December 18, as well outside of all 8 of Middletown's elementary school! 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