Holiday on Main Street presents The Magic of Middletown will once again be held in Downtown Middletown on the weekends from Thanksgiving to Christmas.

Schedule of Events:

Friday, November 25, 2022

Magic of Middletown Tree Lighting Ceremony

4:00 – 8:00 p.m.

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!

5:00 – 6:00 p.m.- South Green– Join the Carol Sing with Middletown High School Concert Choir and the Beman Middle School Choir, sponsored by Middletown Commission on the Arts, with Emcee Trevor Davis from Trevor Davis Commercial Real Estate, LLC!

5:40 p.m. – Led by the Middletown High School Marching Band, Santa and Deputy Mayor Vinnie Loffredo arrive by the Holiday Wagon Ride for the Tree Lighting on the South Green!

6:00 p.m. – TREE LIGHTING on the South Green – The Deputy Mayor and Santa Claus will turn on the lights on the big tree on the South Green!

6:15 p.m. – The Beman Middle School Band will lead the 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 Deputy Mayor turn on the Lights on the Tree, donated by Kronenberger & Sons Restoration, on the Chamber Roof!

Free Pictures with Santa, courtesy of Pratt & Whitney in front of the Church of the Holy Trinity, immediately following the Tree Lighting at the Chamber! Pictures will be taken by Lori Lodge!

8:15 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 Treats 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 26, 2022

Shop ’til You Drop Christmas Extravaganza

10:00 AM to 2:00 PM

Small Business Saturday– support our local businesses by shopping small!

Check out our Shop ’til You Drop Christmas Extravaganza! Are you looking for that last minute gift or want to support a small local artisan? Come stop by one of the many 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 Civitan Club of Middletown!

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 and email your images to [email protected]. All emails must be received by 3:00PM on Saturday, November 26 to be entered into the drawing. Upon submission of your email, you will be added to our weekly drawing for a $100 downtown business district gift card. Winner will be announced on Monday, November 28 via social media and email.

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 horse & wagon rides down our beautiful Main Street!

11:30 a.m. – 1:30 p.m. – Enjoy the sounds of the holidays as The Connecticut Yuletide Carolers stroll up and down Main Street performing beautiful holiday music sung acapella in four-part harmony!

11:30 a.m. – 12:00 p.m. – Enjoy a holiday story time with the Mayor of Middletown Ben Florsheim at Wesleyan RJ Julia Bookstore (413 Main Street)

Saturday, December 3, 2022

2nd Annual Reindeer Games

10:00 AM to 2:00 PM

Join us for our Second Annual Reindeer Games, officiated by the Middletown Recreation Department! Gather your family and friends, and participate in our Reindeer games! These games will be fun for everyone so bring your winning attitude and team spirit!

Enjoy popcorn and hot pretzels outside of the Chamber, served up by the DAV!

“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 and email your images to [email protected]. All emails must be received by 3:00PM on Saturday, December 3 to be entered into the drawing. Upon submission of your email, you will be added to our weekly drawing for a $100 downtown business district gift card. Winner will be announced on Monday, December 5 via social media and email.

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 horse & wagon rides down our beautiful Main Street!

11:00 a.m. – 1:00 p.m. – Stop by Santa’s Craft Cave to make a Christmas ornament for your tree while enjoying a holiday movie on the big screen! (Santa’s Craft Cave located in the basement of the Middlesex Chamber, 393 Main St)

11:30 a.m. – 12:00 p.m. – Enjoy a holiday story time with Middletown’s Fire Chief Jay Woron at Wesleyan RJ Julia Bookstore (413 Main Street)

1:00 p.m. – Enjoy a Lion Dance along the sidewalks of Main Street performed by Tat Wong Kung Fu Academy! Lion Dance is a loud, funny and exciting traditional Chinese ceremony, usually done by Kung Fu practitioners, and performed at special events.

Stop by Santa’s Mailbox and drop off your letter which will head straight to the North Pole! Located at all 8 of Middletown’s elementary schools as well as the Chamber of Commerce until December 17.

Other events to enjoy

9:00 a.m. to 3:00 p.m. – Annual Holiday Fair & Silent Auction at the Church of the Holy Trinity (381 Main St), featuring 2 floors full of 30+ crafters, baked goods, Vermont cheeses, hand-made goods, a Silent Auction, an African Safari Trip to bid on, gift baskets, and MORE! The quilt raffle is back this year with a beautiful handmade, queen sized quilt! There will be a food truck on site that will have lunch for purchase. For more information, contact 860-347-2591.

10:30 a.m. – 11:30 a.m. – UmoJamz Kwanzaa Author Visit and Storytime at Russell Library! Enjoy a special Kwanzaa storytime where you can meet the Authors of the wonderful UmoJamz book series; Rayna Walters. Kurt Zimmermann and Garrett Griffin, Jr! This program is intended for children ages 3 – 8 years old and a caregiver, but all ages are welcome!

Saturday, December 10, 2022

Dashing Through Downtown Day

10:00 AM to 2:00 PM

Enjoy popcorn and hot pretzels outside of the Chamber, served up by the Rotary Club of Middletown!

“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 and email your images to [email protected]. All emails must be received by 3:00PM on Saturday, December 3 to be entered into the drawing. Upon submission of your email, you will be added to our weekly drawing for a $100 downtown business district gift card. Winner will be announced on Monday, December 5 via social media and email.

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 horse & wagon rides down our beautiful Main Street!

11:00 a.m. – 1:00 p.m. – Stop by Santa’s Craft Cave to make a Christmas ornament for your tree while enjoying a holiday movie on the big screen! (Santa’s Craft Cave located in the basement of the Middlesex Chamber, 393 Main St)

11:30 a.m. – 12:00 p.m. – Enjoy a holiday story time with Middletown’s Police Chief Erik Costa at Wesleyan RJ Julia Bookstore (413 Main Street)

11:30 a.m. – 1:30 p.m. – Enjoy live music by Bryan Titus as he performs holiday favorites outside of Webster Bank!
Stop by Santa’s Mailbox and drop off your letter which will head straight to the North Pole! Located at all 8 of Middletown’s elementary schools as well as the Chamber of Commerce until December 17.

Dashing through Downtown Holiday Parade

Parade kicks off at 6:30 PM

Join us for our third 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 6:15 p.m.

Registration will be from 4:00-6:00 pm. Help us fill Santa’s Summer sleigh by donating a toy to benefit Middletown families. $5 registration fee per vehicle.

The parade will take off at 6:30 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!!

5:30 p.m. – Looking for some 21+ fun?! Join us on our double-decker bus for our 2nd Annual Magic of Middletown Pub Crawl which will participate in our Holiday Parade and then will make stops at Eli Cannons Tap Room, Esca, and Sicily Coal Fired Pizza. Enjoy drink specials, giveaways, trivia, an ugly sweater contest, and more!

Date:
November 25 - 26, 2022
December 3 & 10, 2022

Location: Downtown Middletown, CT

Click here for more information.