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 27 - Magic of Middletown Tree Lighting Ceremony
- 4:00 p.m. - 8:00 p.m.- Middlesex County Chamber of Commerce– Join us in front of the Chamber office for popcorn & hot pretzels served up by The Kiwanis Club of Middletown as well as Free Wagon Rides on Main Street. The wagon rides will take a short break while the Tree Lighting is happening on the South Green and the Rides will resume after the Tree Lighting at the Middlesex Chamber!
- 4:30 p.m. - South Green- Enjoy a kung fu demonstration by Middletown’s own Tat Wong Kung Fu Academy on Main Street. Watch members of the Tat Wong Kung Fu Academy perform individual and group forms, weapons & bare hand and self-defense…just like in the movies!
- 5:00 – 6:00 p.m.- South Green– Join the Carol Sing with Middletown High School Concert Choir under the direction of Stephanie Zak and the Beman Middle School Choir under the direction of Kaylin Tulley & Kaleb Watson, sponsored by Middletown Commission on the Arts, with a special emcee!
- 5:40 p.m. – Led by the Middletown High School Band under the direction of Kimberly Rodriguez and Kelsi Harmon and the Beman Middle School Band under the direction of Amy Babineau , Santa, Mrs. Claus, Mayor Gene Nocera, and 3rd grade Middletown students (who were chosen by their teachers to receive a certificate for their good citizenship, good behavior, respect towards others and demonstration of the spirit of giving in everyday life!) arrive for the Tree Lighting on the South Green!
- 6:00 p.m. – TREE LIGHTING on the South Green- The Mayor and Santa Claus will turn on the lights on the big tree on the South Green!
- 6:15 p.m. – Join our parade up Main Street with a stop at Spear Park to light the Holiday Display and then proceed to the Middlesex County Chamber of Commerce (393 Main St), where Santa and the Mayor turn on the Lights on the Tree, donated by Kronenberger & Sons Restoration, on the Chamber Roof!
- Take your own Picture with Santa in front of the Church of the Holy Trinity, immediately following the Tree Lighting at the Chamber! Santa will be around for you to take pictures until 7:30 p.m.
- 7:45 p.m. - Annual Tree Lighting in front of Eli Cannon’s Tap Room, 695 Main Street, where SANTA will arrive by fire engine to light the tree. Elves will be on the sidewalk with Popcorn, Cookies, Hot Chocolate and goodies for the kids, and The Middletown Police Benefit Association Pipe & Drum Corps will be playing to welcome the arrival of Santa! Don't forget to bring an unwrapped toy for the Police Department's Stuff-A-Cruiser fundraiser!
Saturday, November 28 - Holiday Pop-up Vendor Fair
10:30 AM to 1:30 PM
- Check out our Holiday Pop-up Vendor Fair! Are you looking for that last minute gift or want to support a small local artisan? Come stop by one of over 15 vendor’s set-up along Main Street and then stop into one of the many stores downtown!
- Enjoy popcorn and hot pretzels outside of the Chamber served up by the DAV!
- Take your own picture with Santa on his sleigh! Santa will once again be pulling his sleigh with the help of his favorite reindeer! Take your social media-worthy picture with Santa before he heads back to the North Pole!
- Enjoy free wagon rides down our beautiful Main Street!
- “Tis the Season to Find a Gnome” Scavenger Hunt- Jingles the Gnome has escaped the Chamber in hopes of finding some holiday magic! Solve the riddle and help us find Jingles at different locations throughout downtown. Take a picture of Jingles (or you in front of Jingles) at all locations be entered to win a gift basket and a Downtown Business District Gift Card!
- 10:30 - 11:00 a.m. - Enjoy a holiday story time at Wesleyan RJ Julia Bookstore (413 Main Street) with a special guest!
Saturday, December 5 - North Pole Returns to Middletown
10:30 AM to 1:30 PM
- Enjoy popcorn and hot pretzels outside of the Chamber served up by the Civitan Club of Middletown!
- Take your own picture with Santa on his sleigh! Santa will once again be pulling his sleigh with the help of his favorite reindeer! Take your social media-worthy picture with Santa before he heads back to the North Pole!
- Enjoy free wagon rides down our beautiful Main Street!
- Stop by the Middletown Fire Department table and pick up some goodies!
- “Tis the Season to Find a Gnome” Scavenger Hunt- Jingles the Gnome has escaped the Chamber in hopes of finding some holiday magic! Solve the riddle and help us find Jingles at different locations throughout downtown. Take a picture of Jingles (or you in front of Jingles) at all locations be entered to win a gift basket and a Downtown Business District Gift Card!
- 10:30 - 11:00 a.m. - Enjoy a holiday story time at Wesleyan RJ Julia Bookstore (413 Main Street) with a special guest!
Friday, December 11 - Dashing through Downtown Holiday Parade
Parade kicks off at 7:00 PM
- Join us for our fifth annual decorated vehicle parade! Decorate your car, van, truck, flatbed, a sleigh, whatever you have! Don’t forget, the more decorations, the better! Participating vehicles will register and lineup at Middletown High School and will parade through downtown Middletown, led by Santa, to view the fabulous decorations on display.
- This year, enjoy a little friendly competition for the most festive vehicles! Mayor Gene Nocera, Jingles the Gnome, and Santa will select their favorite vehicles in the parade! Judging will take place at 6:45 p.m.
- Registration will be from 4:30-6:30 pm. Bring an unwrapped toy to benefit the Middletown Police Department's Toy Drive. $5 registration fee per vehicle.
- The parade will take off at 7:00 p.m. SHARP! Don’t be late!
- You can also catch the parade as it travels down Main Street! Setup behind your car and get ready to enjoy the beautiful parade!!
Friday, December 11 - Dashing through Downtown Holiday Parade
5:30 - ???
Join us for a festive night of holiday fun as we kick off the season with the ELF-ed Up Pub Crawl! Grab your friends, wear your best ugly holiday sweater, and get ready for an unforgettable evening on Main Street.
Event Highlights
- Ride on our decorated holiday pub-crawl bus which kicks off the night by participating in the Middletown Decorated Holiday Vehicle Parade
- Visit several Downtown Middletown establishments
- Take part in our Ugly Sweater Contest
- Enjoy giveaways, contests, laughs, and plenty of holiday cheer
Schedule Snapshot
A detailed schedule will be sent to all participants before the event, but here's a quick overview:
- 5:30 p.m. to 6:15 p.m. - Arrival & check-in
- 6:20 p.m. - Bus departs Downtown Middletown to line up at Middletown High School to participate in Decorated Holiday Vehicle Parade.
- 7:00 p.m. - Parade takes off from Middletown High School and travels through Downtown Middletown
- After Parade: Evening pub crawl, visiting multiple local spots throughout Downtown
What to Know
A full what to bring list and all final details will be included in your reminder email sent to you a few days prior to the event.
Ugly Sweater Contest
Wear your ugliest holiday sweater for your chance to win a prize!
Saturday, December 12 - Paws & Claus Day
10:30 AM to 1:30 PM
- Enjoy popcorn and hot pretzels outside of the Chamber!
- “Tis the Season to Find a Gnome” Scavenger Hunt- Jingles the Gnome has escaped the Chamber in hopes of finding some holiday magic! Solve the riddle and help us find Jingles at different locations throughout downtown. Take a picture of Jingles (or you in front of Jingles) at all locations be entered to win a gift basket and a Downtown Business District Gift Card!
- Take your own picture with Santa on his sleigh! Santa will once again be pulling his sleigh with the help of his favorite reindeer! Take your social media-worthy picture with Santa before he heads back to the North Pole!
- Paws & Claus photos! Take a PAWSOME picture of your pet with Santa!!!
- Enjoy free horse & wagon rides down our beautiful Main Street!
- 10:30 - 11:00 a.m. - Enjoy a holiday story time at Wesleyan RJ Julia Bookstore (413 Main Street) with a special guest!
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 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!