The wonder of it all: Ridgefield’s Holiday Stroll turns 20
Ridgefield’s Holiday Stroll will celebrate two decades of horse and carriage rides and ice-carving fun this December.
The annual event, which has attracted Hallmark cameras to the village and inspired copycat celebrations around the region, kicks off Friday, Dec. 6, from 5 p.m. to 10 p.m. and will run through Saturday, Dec. 7, from 9 a.m. to 8 p.m.
“Other towns do it but nothing is quite like ours,” said Billy Craig of the Downtown Ridgefield merchants association. “And that’s because not every town has a Main Street like ours. It’s really a great setting for this picturesque event.”
Craig, who owns Craig Jewelers on Main Street has been organizing the Holiday Stroll in town for 20 years alongside Kathy Graham of Fairfield County Bank.
“People keep coming back because it’s an event for all ages,” said Graham. “There’s so much going on throughout the downtown, whether it’s writing postcards for the troops at Lounsbury House or RMAC and Cheese at the Ridgefield Library … It’s become a holiday tradition for families here and it’s just kept growing beyond our wildest dreams.”
When Craig and Graham started planning the first Stroll 20 years ago, they had no idea Ridgefield’s Holiday Stroll would be as popular as it has become.
“When we started out, we had no idea what we were doing,” said Graham. “All of the credit goes to the merchants who put so much time and effort into planning this event and coming up with ideas to make it better each and every year.”
In addition to the ice sculptures and the horse and carriages, there will be singing Toy Soldiers, strolling Christmas carolers, magic shows, and breakfast with Santa on Saturday morning at the Boys and Girls Club.
New this year will be an ugly sweater contest for families that will run on Saturday from 2 to 3 p.m.
“There will be judges on Main Street, so wear your ugly sweaters that day,” said Graham.
“Megan Searfoss at Ridgefield Running is heading up this great project and there will be registration forms online and more information on it in the weeks to come,” added Craig. “People won’t miss it, we promise.”
The ugly sweater contest will also help promote shopping on Saturdays — something that Graham and Craig have been pushing for over the last several years.
“Saturday is the more family-oriented day — there’s the pancake breakfast in the morning and magician Tom Pesce will be doing two shows in front of town hall in the afternoon,” Graham said, “but there’s also a great opportunity for people to get a brochure Friday night and fill in their wish list items and then come back to shop Saturday.”
The strolling Toy Soldiers will make appearances both days, and ice sculpture artist Bill Covitz will be creating a Frozen-themed carving on the green next to Prime Burger on Friday night.
There will also be ice sculptures all around town in front of various Main Street storefronts throughout the weekend.
“Those will be themed around the businesses,” said Craig.
“We have all the traditional things that everyone looks forward to — horse and carriage rides from Lounsbury to the library, live ice sculpting, and the Ridgefield Chorale singing all your holiday favorites,” added Graham.
The ugly sweater contest isn’t the only new event though this year.
The organizers said that Lounsbury House — the hub for all of Ridgefield’s nonprofits during the Stroll — will be hosting the Ridgefield Rotary Club and its new “Ridgefield-opoly” on Friday night.
“We don’t want to project but I think this is going to be very popular,” said Craig. “They’ve recreated the Monopoly board with all things Ridgefield. For anybody who loves this town, you’re going to want to see this. It’s something that’s very fun.”
Craig said he cherishes the moments during the Stroll when he walks outside his business and sees the crowds on Main Street.
“It’s always been the best part,” he said, “just walking outside and taking that small break and seeing the mass of people. There are horses, there’s people singing — everybody’s always happy. It’s exactly why Hallmark has come with cameras to our little town — it’s a magical moment.”
Graham said what she enjoys most about the Stroll is how it brings everyone together.
“It’s a small town so everyone needs to pull together to make this happen every year and, sure enough, they keep pulling together and making it better each and every year,” she said. “It’s a beautiful town and we’re just happy that this is the event that gets to highlight and celebrate that fact. It’s a townwide party and there’s nothing else quite like it.”