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Holiday on Main Street presents The Magic of Middletown!

Join us once again for Holiday on Main Street presents The Magic of Middletown! 

Friday, November 26 : 4:00 - 8:00PM Magic of Middletown Tree Lighting Ceremony

Saturday, November 27 : 10:00AM - 2:00PM Small Business Saturday

Saturday, December 4 : 10:00AM - 2:00PM first ever Reindeer Games

Saturday, December 11 : 10:00AM - 2:00PM for a Holiday Pop-up Vendor Fair

Saturday, December 18 : 2nd Annual Dashing Through Downtown Decorated Vehicle Parade, dashing off from Middletown High School at 6:30PM

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!