Artistic rendering – Event may differ
Holiday on Main Street: Magic of Middletown
Annual Holiday on Main Street celebration with themed weekend events.
About
Experience the 'Magic of Middletown' during the 40th Annual Holiday on Main Street event series. This festive celebration transforms Downtown Middletown into a winter wonderland with a variety of weekend activities from Thanksgiving through Christmas. Highlights include a tree lighting ceremony, a pop-up vendor fair, special themed days like 'North Pole Comes to Middletown' and 'Paws & Claus', and a unique decorated vehicle parade.
Our Take
Family Friendly
Best For
Families and holiday shoppers
Vibe
Festive and community-oriented
Energy Level
Moderate
Budget
$
Photo Friendly
Weather Sensitivity
High
Special Events & Promotions
- Magic of Middletown Tree Lighting Ceremony
- Annual Holiday Pop-up Vendor Fair
- North Pole Comes to Middletown Day
- Paws & Claus Day
- Dashing Through Downtown Decorated Vehicle Parade and Pub Crawl
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.
Location
Event Details
Pricing
$
Duration
Varies by event day
Ages
All ages
Neighborhood
Downtown Middletown
Timed Entry
No
Organizer
Middlesex County Chamber of Commerce
Practical Information
Parking
FREE parking in CITY PARKING LOTS during Holiday On Main Street. Main Street parking will be monitored.
Pet Policy
Service animals only
Food & Drink
Beverage vendors available
Quick Actions
Tips & Advice
- Mail your letters to Santa from the special mailbox at the Chamber of Commerce between November 24th and December 15th for a chance to receive a reply.
- Check the official website and social media for any weather-related postponement or cancellation notices.
- Take advantage of the free parking available in city parking lots throughout the event.
- Arrive early on vendor fair days to get the best selection of unique holiday items.
- Consider attending the Dashing Through Downtown Decorated Vehicle Parade and Pub Crawl for a unique evening experience.
Frequently Asked Questions
What are the main dates for Holiday on Main Street?
The event series runs on weekends from November 28, 2025, through December 19, 2025.
Is there parking available?
Yes, parking is free in city parking lots during the event.
Can I send a letter to Santa?
Absolutely! Santa's Mailbox will be at the Chamber of Commerce from November 24th to December 15th.
What happens if there is bad weather?
Inclement weather updates, including postponements or cancellations, will be posted on the official website and social media channels.
What kind of vendors can I expect?
The Holiday Pop-up Vendor Fair on November 29th will feature various vendors offering holiday-themed items and crafts.
