Holiday on Main Street presents The Magic of Middletown!
Join us once again for Holiday on Main Street presents The Magic of Middletown!
- 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! Don't forget to stop by the Middletown High School Crew Team's annual bake sale in front of the Church of the Holy Trinity!
- 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, sponsored by Middletown Commission on the Arts, with Emcee Trevor Davis from Trevor Davis Commercial Real Estate, LLC!
- 5:15 - 6:00 p.m. - Lastrina Girls Bridal Salon - Enjoy a Live Ballerina Bringing Magic to Lastrina Girls Bridal Salon Window- Lastrina Girls Bridal Salon will feature a live ballerina in their holiday window performing excerpts from an Ekklesia Contemporary Ballet production.
- 5:40 p.m. – Led by the Middletown High School Band under the direction of Kimberly Rodriguez and Kelsey 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!
Stop by Santa's Mailbox located outside of the Middlesex Chamber and drop off your letter between November 26 and December 15 which will head straight to the North Pole! Make sure to include your address as Santa will be replying to some letters!
Please visit www.HolidayOnMain.com for more info! Don't forget to share your images online using #magicofmiddletown2025
10:00 AM to 2:00 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 Middletown’s Mayor Gene Nocera
Other events to enjoy:
- 10:30 a.m. - Come join the Russell Library for a ride on the Polar Express as it travels to the North Pole for the holidays. We will enjoy a reading of the classic story The Polar Express with special guest Conductor Phil Pessina. Come dressed in your pajamas.
- 11:00 a.m. - 8:00 p.m. - Jump on and off the holiday trolley while you shop, dine, and explore downtown Middletown! The trolley, provided by River Valley Transit will be making stops at all city parking lots! Trolley runs Saturdays and Sundays from 11:00 a.m. to 8:00 p.m. from November 25- December 20. https://rivervalleytransit.com/schedules/middletown-holiday-trolley/
- 7:00 p.m. - “A Christmas Carol” performed by the East Haddam Stage Company @ Russell Library. Celebrate the season by spending an enchanting evening with Ebenezer Scrooge and the Christmas Ghosts that help him find the meaning of the holiday. This show will run Saturdays and Sundays, November 29th - December 21st. Tickets for this library fundraiser will only be sold online @ russelllibrary.org
- Wesleyan Potters’ Annual Holiday Sale: Friday, Nov 28 - Wednesday, Dec 24, at 350 S. Main Street, Middletown. Experience the beauty of artistry and craft through exquisite handmade works in pottery, jewelry, wood, stone, glass, and fiber. Open daily 10:00am to 6:00pm, Black Friday through Christmas Eve. Additional free parking located in the rear - accessible from Birdsey Avenue. For more info call 860-347-5925, or visit www.wesleyanpotters.com.
Stop by Santa's Mailbox located outside of the Middlesex Chamber and drop off your letter between November 26 and December 15 which will head straight to the North Pole! Make sure to include your address as Santa will be replying to some letters!
10:00 AM to 2:00 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 Middletown’s Fire Chief David Albert!
Other events to enjoy:
- 11:00 a.m. - 8:00 p.m. - Jump on and off the holiday trolley while you shop, dine, and explore downtown Middletown! The trolley, provided by River Valley Transit will be making stops at all city parking lots! Trolley runs Saturdays and Sundays from 11:00 a.m. to 8:00 p.m. from November 25- December 20. https://rivervalleytransit.com/schedules/middletown-holiday-trolley/
- 7:00 p.m. - “A Christmas Carol” performed by the East Haddam Stage Company @ Russell Library. Celebrate the season by spending an enchanting evening with Ebenezer Scrooge and the Christmas Ghosts that help him find the meaning of the holiday. This show will run Saturdays and Sundays, November 29th - December 21st. Tickets for this library fundraiser will only be sold online @ russelllibrary.org
- Wesleyan Potters’ Annual Holiday Sale: Friday, Nov 28 - Wednesday, Dec 24, at 350 S. Main Street, Middletown. Experience the beauty of artistry and craft through exquisite handmade works in pottery, jewelry, wood, stone, glass, and fiber. Open daily 10:00am to 6:00pm, Black Friday through Christmas Eve. Additional free parking located in the rear - accessible from Birdsey Avenue. For more info call 860-347-5925, or visit www.wesleyanpotters.com.
- Sunday, December 7 - 11:00 a.m. - Story Time with The Grinch! - Wesleyan RJ Julia Bookstore Bring your little ones to a fun and engaging holiday story time with none other than the Grinch himself! Perfect for kids who love stories, this free event is a great way to foster a love of reading while enjoying quality time together and embracing the holiday spirit. Our featured book this week will be How the Grinch Stole Christmas!, a charming and classic tale that’s sure to delight young readers and spark their imaginations.
Stop by Santa's Mailbox located outside of the Middlesex Chamber and drop off your letter between November 26 and December 15 which will head straight to the North Pole! Make sure to include your address as Santa will be replying to some letters!
Please visit www.HolidayOnMain.com for more info! Don't forget to share your images online using #magicofmiddletown2025
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 Ben Florsheim, 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!!
- 6:00 p.m. - ?? - Looking for some 21+ fun?! Join us on our double-decker bus for our 4th Annual Magic of Middletown Pub Crawl which will participate in our Holiday Parade and then will make stops some local favorite establishments in downtown Middletown. Enjoy drink specials, giveaways, trivia, an ugly sweater contest, and more! For more info, CLICK HERE.
10:00 AM to 2:00 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 Middletown’s Police Chief Erik Costa!
Other events to enjoy
- 8:30 a.m. – 12:30 p.m. – The Middlesex United Way and Middletown Police Department will be collecting unwrapped toys for their annual Stuff-A-Cruiser Holiday Toy Drive outside of Main Street Market. Donate an unwrapped gift for a child (grades 6-12) and help make their holiday brighter!
- 11:00 a.m. - 8:00 p.m. - Jump on and off the holiday trolley while you shop, dine, and explore downtown Middletown! The trolley, provided by River Valley Transit will be making stops at all city parking lots! Trolley runs Saturdays and Sundays from 11:00 a.m. to 8:00 p.m. from November 25- December 20. https://rivervalleytransit.com/schedules/middletown-holiday-trolley/
- 7:00 p.m. - “A Christmas Carol” performed by the East Haddam Stage Company @ Russell Library. Celebrate the season by spending an enchanting evening with Ebenezer Scrooge and the Christmas Ghosts that help him find the meaning of the holiday. This show will run Saturdays and Sundays, November 29th - December 21st. Tickets for this library fundraiser will only be sold online @ russelllibrary.org
- Wesleyan Potters’ Annual Holiday Sale: Friday, Nov 28 - Wednesday, Dec 24, at 350 S. Main Street, Middletown. Experience the beauty of artistry and craft through exquisite handmade works in pottery, jewelry, wood, stone, glass, and fiber. Open daily 10:00am to 6:00pm, Black Friday through Christmas Eve. Additional free parking located in the rear - accessible from Birdsey Avenue. For more info call 860-347-5925, or visit www.wesleyanpotters.com.
Stop by Santa's Mailbox located outside of the Middlesex Chamber and drop off your letter between Nov 26 and Dec 15 which will head straight to the North Pole! Make sure to include your address as Santa will be replying to some letters!
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!