Saturday – 11/25/2023

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Shop ’til You Drop Christmas Extravaganza

10:00 AM to 2:00 PM
  • Small Business Saturday– support our local businesses by shopping small!
  • Check out our Shop ’til You Drop Christmas Extravaganza! Are you looking for that last minute gift or want to support a small local artisan? Come stop by one of the many vendor’s set-up along Main Street and then stop into one of the many stores downtown!
  • Enjoy popcorn and hot pretzels outside of the Chamber, served up by the Rotary Club of Middletown!
  • 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 a picture of Jingles (or you in front of Jingles) at all locations and email your images to [email protected]. All emails must be received by 3:00PM on Saturday, November 25 to be entered into the drawing for a $100 downtown business district gift card. Winner will be announced on Monday, Nov 27 via email & social media.
  • Take your own picture with Santa on his sleigh! Santa will once again be pulling his sleigh with the help of his favorite reindeer! Take your social media-worthy picture with Santa before he heads back to the North Pole!
  • Enjoy free horse & wagon rides down our beautiful Main Street!
  • 10:30 – 11:00 a.m. – Enjoy a holiday story time with the Mayor of Middletown Ben Florsheim at Wesleyan RJ Julia Bookstore (413 Main Street)
  • 11:00 a.m. – 1:00 p.m. – Stop by Santa’s Craft Cave to make a Christmas ornament for your tree while enjoying a holiday movie on the big screen! Santa’s little helpers will be on hand to help with ideas and more! (Santa’s Craft Cave located in the basement of the Middlesex Chamber, 393 Main St)
  • Stop by the Kids’ Department at Wesleyan RJ Julia Bookstore any time during store hours between November 25th and December 15th; there, you will find all the tools and supplies you need to write the perfect letter to Santa! Then, head to Santa’s Mailbox right next door at the Chamber of Commerce to send your letter directly to the North Pole. Please be sure the child’s name and address are on the letter, so Santa can respond.
Holiday Pop-up Vendor Fair

Join us by setting up a table and selling your products to those in attendance during the holiday season! Bring your handcrafted, unique, or holiday items, information about your company, or just spread the holiday cheer!