The holiday season is upon us and no place captures that sparkling spirit quite like Very Merry Middletown, a joyful series of events that turns the city’s downtown into a winter wonderland.
“Very Merry Middletown stands out by offering something for every age, every budget, every family—all in one walkable, charming historic district,” says Avinne Kiser, founder and board president of Reimagine Middletown.
From ice skating and carriage rides to twinkling lights and a Santa parade, Very Merry Middletown features something to invigorate everyone’s holiday senses.
“It’s a place where everyone can feel the holiday magic together,” Kiser says of the series of events formerly known as Holiday Whopla. The group changed its name to Reimagine Middletown this year.
“Our nonprofit is still officially Holiday Whopla Inc., but we now operate as Reimagine Middletown,” Kiser shares. “The change reflects our long-term vision for expanded, year-round programming.”
The main attraction is Reimagine Ice Rink, an outdoor ice skating rink that, starting in 2026, will remain open year-round by transforming from ice skating in the winter to roller skating and pickleball in the warmer months.
“It’s a stunning outdoor rink surrounded by heated rental igloos and massive interactive light displays,” says Kiser. “It’s the centerpiece of the experience.”
The ice rink is not the only attraction. Light Up Middletown features 96 acres of drive-through holiday light displays. Each year a devoted group of volunteers known as the Grandpa Gang brings the displays to life at Smith Park. This marks the 26th year of this holiday tradition. The attraction dazzles nightly from November 28 through December 31.
Very Merry Middletown’s calendar is packed with festive fun:
- Visits with Santa, Fridays & Saturdays, November 28–December 20: Share your wish list with Santa Claus.
- Santa Parade, November 29: The jolly parade winds through downtown and ends at Governor’s Square, where Santa himself lights the Christmas tree.
- Candlelight Tour of Homes, December 13: Peek inside beautifully decorated historic homes, each with its own unique holiday charm.
- Horse-Drawn Carriage Rides, December 13, 20 & 27: Enjoy an old-fashioned ride through downtown, surrounded by shimmering lights.
- Blitzen Cookie & Cocktail Walk, December 20: A walk featuring holiday cookies paired with cocktails that celebrate the season.
- Ice Skating, November 10–January 11: Take a spin on the ice. Join themed nights like Ugly Sweater, Grinch and even Taylor Swift and Travis Kelce night. Skating lessons are available, too.
- Igloo Rentals, Ongoing: Stay warm and cozy rinkside while enjoying the company of friends.
“Visitors often tell us it feels like stepping into a Hallmark movie,” Kiser says. “There’s sparkling lights, joyful music, festive activity everywhere and that warm sense of community you can’t help but feel.”
Head to nearby Middletown for more merry this season. Reimagine-Middletown.com