The Magic of Middletown presented by Holiday on Main Street

The Magic of Middletown presented by Holiday on Main Street Holiday on Main Street is an annual event held in Downtown Middletown on the weekends from Thanksgiv

There is still time to take a ride on the Holiday Trolley through downtown Middletown courtesy of River Valley Transit! ...
12/17/2025

There is still time to take a ride on the Holiday Trolley through downtown Middletown courtesy of River Valley Transit!

The trolley operates weekends through Christmas and makes stops at the following:
Melilli Plaza Parking Lot
Arcade Lot
Main & College Street
Main & Pleasant
Middlesex Corporate Parking Garage
Middletown Police Department
Main Street Market
Main & Ferry
Main & Rapallo
Melilli Plaza Parking Lot

To learn more, visit: https://rivervalleytransit.com/schedules/middletown-holiday-trolley-2/

Another successful Holiday on Main is in the books! 🎅🏻🎄⛄🎁From our annual 3 Tree Lightings, to our Holiday Pop-up Vendor ...
12/16/2025

Another successful Holiday on Main is in the books! 🎅🏻🎄⛄🎁

From our annual 3 Tree Lightings, to our Holiday Pop-up Vendor Fair, North Pole Returns to Middletown Day, Paws & Claus Day, and our Decorated Vehicle Parade and Pub Crawl, thousands of attendees enjoyed kicking off the holiday season with us. We would like to take a moment to thank all of the city departments involved, Middletown’s Mayor Gene Nocera, Middletown’s Fire Chief David Albert, Middletown’s Police Chief Erik Costa, our fabulous civic groups: The Kiwanis Club of Middletown, Disabled American Veterans Post #7, The Civitan Club of Middletown, The Rotary Club of Middletown, our incredible volunteer committee led by Chairman Al Santostefano, and of course the Middlesex Chamber team for making this event possible.

We would also like to give a huge thank you to our sponsors for their continued support of this event: Presenting sponsors: City of Middletown and Pratt & Whitney; Jingle Bell Sponsors: Downtown Business District and M&T Bank; Snowflake Sponsor: Jarvis Products Corporation; Holly Sponsors: Adelbrook Bark-ery & Adelbooks and More, Community Health Center, Houzpital Property Damage Restoration, Kronenberger & Sons Restoration, LLC, Liberty Bank, Middlesex Health, Middletown Toyota, Root Center for Advanced Recovery Middletown and The Exterior Company; Jingles the Gnome Sponsors: Cavanaugh & Company, LLC, Collaborative ABA Services, LLC, Community Foundation of Middlesex County, Connecticut Rental Center and Dunkin; and Reindeer Sponsors: Harborage Law, Jukonski Truck Sales and Service LTD, IMPACT (previously MARC Community Resources), Middletown Sport Hall of Fame & Museum, Nealon Insulation, Russell Library, The South Fire District and The Growth Chapter LLC.

🎄🚗✨ Another Decorated Car Parade is in the books—and WOW, what a ride! ✨🚗🎄What an incredible day filled with holiday che...
12/13/2025

🎄🚗✨ Another Decorated Car Parade is in the books—and WOW, what a ride! ✨🚗🎄

What an incredible day filled with holiday cheer, creativity, and smiling faces all along the route! A huge THANK YOU to everyone who decked out their vehicles and to the families who came out to wave, cheer, and celebrate with us. You truly made the magic happen.

🎅 Special shoutout to the amazing team at Cromwell Automotive for chauffeuring Santa in serious style, and to Plummer All-Season Landscaping, LLC for letting the Grinch steal the show on their snowmobiles! 💚❄️

This is what community spirit looks like—and we already can’t wait for next year! 🎉🎁

Join us for our final Saturday of events this Saturday, December 13 from 10am-2pm in downtown Middletown! - Enjoy popcor...
12/11/2025

Join us for our final Saturday of events this Saturday, December 13 from 10am-2pm in downtown Middletown!

- Enjoy popcorn and hot pretzels outside of the Chamber served up by Middletown Rotary!
- “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 your own picture with Santa on his sleigh!
- Paws & Claus photos! Take a PAWSOME picture of your pet with Santa!!!
- Enjoy free 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
- 10:00 a.m. - 1:30 p.m. – 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.

Join us for our fifth annual decorated vehicle parade THIS FRIDAY, December 12! Decorate your car, van, truck, flatbed, ...
12/10/2025

Join us for our fifth annual decorated vehicle parade THIS FRIDAY, December 12!

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.

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!

Parade route:
- Leave Middletown High School
- Right onto Newfield St
- Left onto Liberty St
- Continue onto Prospect St
- Right onto Grand St
- Right onto Main St
- Disburse at the South Green

You can also catch the parade as it travels down Main Street! Setup behind your car and get ready to enjoy the beautiful parade!!

Week 2 Jingles the Gnome scavenger hunt clues!
12/06/2025

Week 2 Jingles the Gnome scavenger hunt clues!

Join us today in downtown Middletown for North Pole Returns to Middletown day from 10am-2pm. Enjoy popcorn and pretzels,...
12/06/2025

Join us today in downtown Middletown for North Pole Returns to Middletown day from 10am-2pm. Enjoy popcorn and pretzels, wagon rides, a story time with Middletown’s Fire Chief David Albert, and don’t forget to stop into the Church of the Holy Trinity for their annual Vendor Fair featuring dozens of unique vendors!!

This year's Holiday on Main Street series of events would not be possible without the amazing support of our sponsors! P...
12/02/2025

This year's Holiday on Main Street series of events would not be possible without the amazing support of our sponsors!

Presenting sponsors: City of Middletown and Pratt & Whitney; Jingle Bell Sponsors: Downtown Business District and M&T Bank; Snowflake Sponsor: Jarvis Products Corporation; Holly Sponsors: Adelbrook Bark-ery & Adelbooks and More, Community Health Center, Houzpital Property Damage Restoration, Kronenberger & Sons Restoration, LLC, Liberty Bank, Middlesex Health, Middletown Toyota, Root Center for Advanced Recovery Middletown and The Exterior Company; Jingles the Gnome Sponsors: Cavanaugh & Company, LLC, Collaborative ABA Services, LLC, Community Foundation of Middlesex County, Connecticut Rental Center and Dunkin; and Reindeer Sponsors: Harborage Law, IMPACT formerly known as MARC Community Resources, Jukonski Truck Sales and Service LTD, Middletown Sport Hall of Fame & Museum, Nealon Insulation, Russell Library, The South Fire District and The Growth Chapter LLC.

Week 1 Jingles the Gnome scavenger hunt!
11/29/2025

Week 1 Jingles the Gnome scavenger hunt!

Thank you for your continued support!!!!
11/29/2025

Thank you for your continued support!!!!

Wishing you and yours a very Happy Thanksgiving!! We look forward to seeing you all downtown tomorrow evening for our an...
11/27/2025

Wishing you and yours a very Happy Thanksgiving!!

We look forward to seeing you all downtown tomorrow evening for our annual Tree Lighting ceremony!

Activities will begin at the Middlesex Chamber at 4:00 p.m.
Tree lighting on the South Green at 6:00 p.m.
Tree lighting at the Chamber at 6:15 p.m.
Tree lighting at Eli Cannons at 8:00 p.m.

Free wagon rides and pictures with Santa will take place throughout the evening!

Address

393 Main Street
Middletown, CT
06457

Opening Hours

Monday 8am - 4:30pm
Tuesday 8am - 4:30pm
Wednesday 8am - 4:30pm
Thursday 8am - 4:30pm
Friday 8am - 4:30pm

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