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Holiday on Main Street presents The Magic of Middletown!

The Holiday on Main Street Planning Committee continues to work with the City of Middletown's Health Department to follow the Governor's guidelines to ensure that these events follow all required guidelines, while still providing safe and family friendly fun!

Our 2020 Holiday on Main Street presents The Magic of Middletown featured the following events:

Friday, November 27 for our first ever VIRTUAL TREE LIGHTING!

View the Virtual Tree Lighting HERE

Saturday, November 28 from 10:00AM - 2:00PM for Small Business Saturday

Friday, December 4 for our Dashing Through Downtown- Decorated Vehicle Parade, dashing off from Middletown High School at 6:15PM

View the Dashing Through Downtown Virtual Vehicle Parade HERE

Saturday, December 12 from 10:00AM - 2:00PM for a Holiday Pop-up Vendor Fair and Spectacular Savings Saturday

For more information, please visit

For more information, please contact Haley Stafford

by email or by phone at 860-347-6924

Holiday on Main Street is an annual Downtown Middletown event which begins the day after Thanksgiving and continues the following four Saturdays. 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!