Week One 29th Annual Holiday On Main St Middletown, CT, is this Friday & Saturday, and Middletown will kick off the 29th Annual Holiday On Main St. This will be the first of four weekends of events leading up to Christmas week. This first weekend will be two days of events, and the themes are Rockin' Around The Christmas Tree and Jingle Bells. Each weekend will have its own theme and will be packed full of activities. Below is the schedule for both Friday and Saturday.