On the Friday after Thanksgiving, Middletown lights its holiday trees in a sequence that starts on the South Green, climbs onto the roof of the Chamber of Commerce and ends at a tap room at 695 Main Street. Three different hosts light trees at three addresses over almost two hours. The Middlesex County Chamber of Commerce's Holiday on Main Street schedule lays the night out that way on purpose. Downtown's holiday season comes from the people who work on Main Street, so this year the route runs past a bar that opened in October, a steel rooftop frame on the old Woolworth building and a few more new spots a block or two away.
Friday, November 27, stop by stop
The night starts well before dark. Here is the sequence the Chamber has posted for the Magic of Middletown Tree Lighting Ceremony.
| Time | Where | What happens |
|---|---|---|
| 4:00 to 8:00 p.m. | In front of the Chamber office | Popcorn and hot pretzels from the Kiwanis Club of Middletown, plus free wagon rides on Main Street |
| 4:30 p.m. | South Green | Kung fu demonstration by Tat Wong Kung Fu Academy |
| 5:00 to 6:00 p.m. | South Green | Carol Sing with the Middletown High School Concert Choir and Beman Middle School Choir, sponsored by the Middletown Commission on the Arts |
| 5:40 p.m. | South Green | The Middletown High School and Beman Middle School bands lead in Santa, Mrs. Claus, Mayor Gene Nocera and the third graders recognized for good citizenship |
| 6:00 p.m. | South Green | Tree lighting by the Mayor and Santa |
| 6:15 p.m. | Main Street | Parade north, with a stop to light the holiday display at Spear Park |
| After the parade | 393 Main St. | Rooftop tree lighting at the Chamber |
| Until 7:30 p.m. | Church of the Holy Trinity | Take your own photos with Santa |
| 7:45 p.m. | Eli Cannon's Tap Room, 695 Main St. | Santa arrives by fire engine to light the tree |
The wagon rides pause while the South Green tree is lit and start again once the parade reaches the Chamber. The rooftop tree at 393 Main was donated by Kronenberger & Sons Restoration.
Every stop has a different host
Look at who runs each stop. The city's tree on the South Green belongs to the Mayor. The Chamber lights its tree on its own roof. A civic club serves food at the Chamber's door. The last lighting of the night happens outside a business, and Eli Cannon's runs it like a block party. Elves hand out popcorn, cookies and hot chocolate on the sidewalk, and the Middletown Police Benefit Association Pipe & Drum Corps plays as Santa pulls up on the fire engine.
That 7:45 lighting also collects toys for the police department's Stuff-A-Cruiser fundraiser, so bring an unwrapped toy if you're walking up from the Chamber.
The rest of the season works the same way, with a different club at the food table for each event. The Kiwanis serve at Friday's tree lighting on November 27, the DAV at the Saturday vendor fair on November 28 and the Civitan Club of Middletown on Saturday, December 5. The prizes stay downtown too. The Saturday scavenger hunt awards a gift basket and a Downtown Business District gift card.
The walk from 393 to 695
Between the Chamber's rooftop lighting and the 7:45 lighting at Eli Cannon's, the addresses on Main Street run from the 300s to the 600s. Several of the buildings along that stretch look different than they did last holiday season.
- Wesleyan RJ Julia Bookstore, 413 Main St. This is a steady stop on the route. It plays a bigger part on Saturday, when it hosts story time.
- The former Woolworth building, 428 Main St. In July, CT Insider reported that the steel frame for a rooftop restaurant and patio could be seen from the street, with work underway to restore the art deco facade.
- Dead Letter Bar, 544 Main St. It opened in early October in a space that has held a string of bars, including Hot Rod's Spotlight Lounge, Hair of the Dog and Keagan's Irish Pub & Restaurant.
- Eli Cannon's Tap Room, 695 Main St. The last tree of the night.
The building with a skeleton on its roof
The Woolworth building is the biggest change along the parade route. The same CT Insider report put developer Dominick DeMartino's estimate for the project at about $8.5 million. About $5 million of that comes from the federal American Rescue Plan Act and the Connecticut Department of Economic and Community Development, as part of a larger effort to revitalize four Main Street buildings. The 87-year-old landmark most recently housed Irreplaceable Artifacts.
Under the plans, the south side becomes a three-story restaurant. It has event space in the basement and dining all the way up to the roof, with about 3,000 square feet indoors inside the steel frame and another 1,700 square feet of patio. The north side's first floor and basement are being marketed as a 4,600-square-foot sports bar. When both venues are full, the building could hold about 500 people.
Christine Marques, Middletown's economic development director, told CT Insider:
"The city has never had a rooftop restaurant before and the views will be spectacular."
In that July report, DeMartino said he expected work to continue through mid- to late 2027. For this year's parade, that means a construction site with a view of the route. The restaurant is still to come.
A new name at 544
CT Insider covered Dead Letter Bar's opening in October. It serves Pacific-inspired food and is open Tuesday through Saturday from 4 p.m. to midnight. Those hours include Friday, November 27, from the first carols on the South Green until well after Santa leaves Eli Cannon's. Among the drink specials the article listed are the Honolulu Haymaker, made with rum, Hawaiian punch, velvet falernum, nutmeg and kombu dashi, and the Black Letter, made with bourbon, black tea vermouth and Amaro Montenegro.
A block off Main, for Saturday morning
The Holiday Pop-up Vendor Fair runs from 10:30 a.m. to 1:30 p.m. on Saturday, November 28. More than 15 vendors set up along Main Street. There are free wagon rides and a Santa photo spot with his sleigh and reindeer, and Wesleyan RJ Julia holds a holiday story time with a special guest from 10:30 to 11. The "Tis the Season to Find a Gnome" scavenger hunt sends families around downtown looking for Jingles the Gnome. Get a photo at every location to be entered for the prize.
That hunt spreads people out from the main corridor, and two new cafes sit just off it.
Arnie's Art Cafe, 107 College St. It opened on September 26 in the former Hubbard Hose #2 firehouse, according to the Hartford Courant. The first floor serves coffee, sandwiches and acai bowls. The front of the room has music and the back is quieter, with a guest sketchbook for anyone who wants to stay and draw. The walls hold one-off pieces that owner D'Avanzo curated from artists around the world, and the space hosts art classes in the evenings. It is open Tuesday through Saturday, so it will be open during the vendor fair.
Two Brothers Cafe, 213 Court St. The Downtown Business District directory lists it as open daily from 6 a.m. to 2 p.m. That puts it on Court Street with coffee before the vendors finish setting up.
Two more Main Street dates in December
The format returns for two more weekends, with new hosts each time.
- Saturday, December 5, 10:30 a.m. to 1:30 p.m.: North Pole Returns to Middletown. The Civitan Club serves popcorn and pretzels. Santa's sleigh, the wagon rides, the gnome hunt and RJ Julia's story time all come back, and the Middletown Fire Department hosts a table with goodies.
- Friday, December 11, 7 p.m.: Dashing through Downtown Holiday Parade. This is the fifth annual decorated-vehicle parade. Vehicles line up at Middletown High School, and registration runs from 4:30 to 6:30 p.m. It costs $5 per vehicle plus an unwrapped toy for the Middletown Police Department's Toy Drive. Mayor Gene Nocera, Jingles the Gnome and Santa judge the most festive entries at 6:45. The parade leaves at 7 sharp and drives down Main Street, where spectators can line the curb.
The ELF-ed Up Pub Crawl runs the same night. Check-in is from 5:30 to 6:15 p.m. A decorated bus leaves downtown at 6:20, rides in the 7 p.m. parade, and then stops at several downtown establishments. There's also an Ugly Sweater Contest. Registration goes through the Chamber.
On December 11, the people who put on Holiday on Main all end up on the same street. The Mayor judges the cars, the police collect the toys, the bars host the crawl and a bus of people in ugly sweaters rides in the parade.
When Main Street lights up, Jennifer Gurnell loves seeing the whole Middlesex County community out together, from the South Green to Eli Cannon's. If you're thinking about a home where downtown evenings like these are a short walk away, let's connect. Start your shoreline search or sale and we'll plan it around the places you'd actually go.
