Holiday on Main Street: Magic of Middletown
Visitors can experience tree lighting ceremonies, musical carol sings, and free wagon rides along Main Street. Festivities include Santa visits, a holiday pop-up vendor fair with local artisans, and downtown scavenger hunts. Guests can also watch a decorated vehicle parade or bring their pets for festive holiday photos.
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Plan Your Visit
Website / Tickets
When
Tickets
Free wagon rides on November 27 and November 28; free horse and wagon rides on December 12.
Hours
Nov. 27: 4:00–8:00 p.m.; kung fu demonstration 4:30 p.m.; carol sing 5:00–6:00 p.m.; tree lighting 6:00 p.m.; Santa pictures until 7:30 p.m.; tree lighting at Eli Cannon’s Tap Room 7:45 p.m. Nov. 28, Dec. 5, and Dec. 12: 10:30 a.m.–1:30 p.m.
Ages
All ages
Neighborhood
Downtown Middletown
Food & Drink
Popcorn and hot pretzels are served at scheduled gatherings; on November 27, cookies, hot chocolate and kids’ goodies are also offered at Eli Cannon’s.
Pets
Pets are welcome for Santa photos during Paws & Claus Day on December 12.
Going?
Location
Tips & Advice
- Bring a camera or phone for your own Santa pictures, which are offered during the November 27 and November 28 activities.
- Visit on November 28 if you want to browse the Holiday Pop-up Vendor Fair, with more than 15 vendors along Main Street.
- Bring your pet for a Santa photo during Paws & Claus Day on December 12.
- On November 27, allow time for the Main Street procession and tree lightings, including the South Green and Eli Cannon’s Tap Room.
- Bring an unwrapped toy if you plan to stop by the November 27 tree lighting at Eli Cannon’s Tap Room, where the Police Department’s Stuff-A-Cruiser fundraiser is taking place.
Special Events & Promotions
- November 27 is the tree-lighting evening, with Santa arriving for the ceremony and available for pictures.
- November 28 is the Holiday Pop-up Vendor Fair; Santa is available for pictures on his sleigh.
- On November 28, completing the gnome scavenger hunt enters participants to win a gift basket and Downtown Business District Gift Card.
- This year, the December 11 vehicle parade has a competition for the most festive vehicles.
- December 12 is Paws & Claus Day, with pet photos with Santa.
Links & Contact
Run by Middlesex County Chamber of Commerce
Christmas Events Near Me is an independent guide, not the organizer of this event. For tickets, entries, vendor spots or questions, contact the organizer directly through their contact page.
Frequently Asked Questions
Is Holiday on Main Street suitable for children and families?
The event welcomes young and old, with activities described as offering something for everyone.
What can visitors do during the celebrations?
Activities include tree lightings, caroling, free wagon rides, Santa pictures, a downtown scavenger hunt, and a vendor fair on November 28.
What food and drink are available?
Popcorn and hot pretzels are offered outside the Chamber on November 27, November 28, and December 5. On November 27, cookies, hot chocolate, and treats for children are available at Eli Cannon’s Tap Room.
Can I bring my pet?
Yes. Bring your pet for a Santa photo during Paws & Claus Day on December 12.
Can visitors take part as vendors or parade entrants?
The November 28 vendor fair features local artisans. The separate December 11 decorated vehicle parade invites vehicle registration, but it is a separate event.
Browse Christmas in Middletown
Always check the official website for the most current information.
We've done our best to keep details up-to-date, but event schedules, prices, and policies can change. For the latest updates, please visit the official website or contact the organizers directly. Christmas Events Near Me is an independent guide and isn't affiliated with the events we list.