Community Corner
Holiday On Main Street In Middletown Details Announced
The event features three tree-lighting ceremonies and a parade along Main Street. Read details on the festivities and activities here.

MIDDLETOWN, CT — Middletown’s 33rd Annual Holiday On Main Street will kick off on Friday, Nov. 23 from 4 p.m. to 8:15 p.m., Chairman of the Middlesex County Chamber of Commerce Central Business Bureau Thomas Byrne announced. The Holiday on Main Street Committee, chaired by Al Santostefano and co-chairman Rich Greco, in conjunction with the City of Middletown, invites everyone to ring in the festive season by attending the three tree-lighting ceremonies and parade along Main Street in Middletown.
Last year, more than 3,000 people were able to enjoy the holiday sights and sounds on the South Green, and more are expected this year. Festivities begin at 4 p.m. with free wagon rides on Main Street. There will be a break while the Tree Lighting is happening on the South Green, and the rides will resume after the Tree Lighting at The Middlesex Chamber. Read more details from the press release below:
In front of Middlesex Chamber, the Kiwanis Club of Middletown members will be selling hot pretzels and popcorn, and in front of the Church of the Holy Trinity, Middletown High School Crew Team will be selling hot chocolate, coffee and desserts.
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A Carol Sing with the Middletown High School Concert Choir will begin at 5 p.m. prior to the tree-lightings, directed by Stephanie Zak, the Woodrow Wilson 7th and 8th Grade Select Chorus directed by Ali Sinicrope and The Keigwin Middle School Chorus directed by Jeannine Westbrook, sponsored by Middletown Commission On the Arts, with Emcee Trevor Davis from Trevor Davis Commercial Real Estate, LLC.
Maisy Mouse will arrive on the Holiday On Main wagon with 3rd grade Middletown students, who were chosen by their teachers because they show good citizenship, good behavior, is respectful to others and demonstrates the spirit of giving in everyday life.
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The first Tree Lighting at 6 p.m. will be the tree on the South Green and will be led by Mayor Daniel Drew and Santa Claus. Immediately following the Tree Lighting, there will be a short pyrotechnic display of Fireworks.
After the tree is lit on the South Green, there will be a Parade up Main Street led by the Middletown High School Band, The Woodrow Wilson Middle School Band, and Santa Claus to the Middlesex Chamber where the tree on the roof will be lit at 6:15 p.m. for the second Tree Lighting of the night followed by free pictures with Santa until 7:45 p.m.
At 8:15 p.m. there will be festivities in front of Eli Cannon’s Tap Room at 695 Main Street for the third and final tree lighting of the night. Santa will arrive to light the tree and there will be elves on hand to provide all children with complimentary popcorn, cookies, hot chocolate and other treats.
On Saturday, Nov.r 24, The Holiday on Main festivities continue from 10 a.m. to 2 p.m. with many family-friendly activities available.
Starting at 10 a.m. until 2 p.m., The Civitan Club of Middletown will sell popcorn and hot pretzels in front of the Chamber with holiday music played by Harvest Woods Audio. The Middletown High School Crew Team will sell hot chocolate, coffee and desserts in front of the Church of the Holy Trinity.
Family activities also begin at 10 a.m., The Fun Train will offer free rides on the sidewalk around downtown until 2 p.m. Bring your camera, children will have the opportunity to meet Santa and enjoy free horse and wagon rides. A holiday photo booth will take fun photos with your friends and family as a remembrance of this year’s holidays, the photo trailer will be located by the crosswalk in front of Holy Trinity Church and is free to all in attendance.
Join Mayor Dan Drew and Maisy Mouse for a Holiday Story Time reading at the Inn at Middletown from 11:30 a.m. to 12 noon. At the end of the reading, there will be a book signing by Maisy Mouse. Bring your camera.
A pet food drive will be held from 10 a.m. to 2 p.m. in front of Holy Trinity Church (381 Main St.) – To benefit the homeless pets at Middletown Animal Control. Please bring donations of: Chew Toys (No Rawhide), Blankets, Towels, Canned Wet Dog & Cat Food, Dry Dog & Cat Food.
For more information, contact: Lauren Middleton at LMiddleton@ForestCityMarketing.com.
There will also be a Kung Fu Demonstration by children and adults who will demonstrate the beauty and power of Kung Fu. The demonstration is presented by Tat Wong Kung Fu Academy starting at 1:30 p.m. to 1:45 p.m. and will take place at Vinnie’s Jump and Jive.
Each Tree Lighting is free of charge to the public. Holiday on Main Street continues on Saturdays December 1, 8, and 15. Parking is free in City parking lots during Holiday On Main Street. Main Street parking will be monitored. Visit www.HolidayOnMain.com for the full schedule and more events during the month of December.
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