Saturday – 12/7/2019



10:00 a.m. – 2:00 p.m.

  • 9:00 a.m. – 10:30 a.m. Free Picture and Donuts with Santa at Vinnie’s Jump & Jive (424 Main St.), courtesy of Middletown Recreation & Community Services Dept.). Donuts courtesy of Dunkin’!
  • 9:00 a.m. – 9:45 a.m. – 5 years & under
  • 9:45 a.m. – 10:30 a.m. – 6 year & over
  • 10:00 a.m. – 2:00 p.m.The Disabled American Veterans – Middletown Chapter #7 will be staffing the popcorn & hot pretzels stand in front of the chamber – stop by to meet them! Also holiday music played by Harvest Woods Audio!
  • 10:00 a.m. – 2:00 p.m. – The fun train will offer Free rides on the sidewalk around the downtown!
  • 10:00 a.m. – 2:00 p.m. – Greet SANTA and enjoy Free horse & wagon rides!
  • 10:00 a.m. to 2:00 p.m. – Holiday Photo Booth – Take 4”x 6” fun photos (No Fee!) with your friends and family as a remembrance of this year’s holidays!  The photo trailer will be located by the crosswalk in front of Holy Trinity Church!
  • 11:30 a.m. – 12 p.m.Holiday Story Time – Splat the Cat will be at Main Street Firehouse (533 Main St.), where Fire Chief Rob Kronenberger will read stories. At the end of the reading, there will be books for sale and a “Book Signing”! Bring your camera!
  • 11:30 a.m. – 1:30 p.m. – Enjoy a performance by The Connecticut Yuletide Carolers as they stroll up and down Main Street performing beautiful holiday music sung a capella in four-part harmony! Traditionally garbed Victorian Carolers will fill the winter air with the bright sounds of the season, bringing holiday cheer to young and old alike! For More information, visit:
  • 12:00 p.m. – 2:00 p.m. – Toy Drive- Donate toys for about 1,000 deserving kids for 96.5 TIC’s Christmas party. Stop by the Chamber and see the Morning Drive personalities Christine & Salt to drop off toys for their Christmas Day Party. The party features face painting, rides, arts & crafts, costume characters, and lunch for roughly 1,000 deserving kids.

Other Events to Enjoy!

  • 9:00 a.m. to 3:00 p.m. – Annual Holiday Craft Fair at The Church of the Holy Trinity (381 Main St), featuring 2 floors full of 40+ crafters, Baked goods, Vermont maple syrup and cheeses, Cookies by the pound, Amaryllis bulbs and live greenery for sale, Hand-made goods, a Silent & Tea Cup Auction, Quilt Drawing, African Safari Trip to bid on, Themed Gift Baskets of all kinds, Tag Sale, Face painting and games for the kids, a visit from Santa, and lunch served from 9 a.m – 2 p.m. For more information, contact (860) 347- 2591
  • 10:00 a.m. – 11:30 a.m. – “Swap Your Stuff, Holiday Style” – Would you like to change out some of your holiday décor, add to your collection, or give away what you can’t use anymore?! Reduce, reuse, recycle! All items remaining at the close of the swap will be donated. Early bird browsing will be available for those who donate on Friday 12/6 — more information at (Russell Library- Hubbard Room)
  • 10:00 a.m. – 12:00 p.m. – “Good and Good For You: Holiday Cookies!” – Registered Dietician Mary Perrino will lead this hands-on cooking class where children will prepare and bake three different kinds of cookies, each featuring yummy, kid-approved ingredients (no peanuts!) that add a little extra bang for the buck. This class is for children ages 8 – 12; parents may watch from the background. Class size is limited and registration is required. Register at (Russell Library- Activity Room)
  • 12:00 p.m. – 4:00 p.m. – The City of Middletown’s Ice Skating Rink will be opening at Veteran’s Memorial Park! Rink hours are Saturday and Sunday from 12:00 p.m. to 4:00 p.m.

    Middletown Residents Non-Residents Season Pass
    Adults $5.00 Adults: $8.00 Resident Family Pass $25.00
    Kids $3.00 Kids $3.00 Resident Individual Pass $15.00

    $4.00 a pair for non-season pass holders

    For more information, visit:

    Photos by De Kine Photo LLC