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 weekend.

The annual event, which has attracted Hallmark cameras to the village and inspired copycat celebrations around the region, kicks off Friday, Dec. 6, from 6 p.m. to 10 p.m. and will run through Saturday, Dec. 7, from 10 a.m. to 5 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’s Fine Jewelry 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,” Graham said. “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,” Graham said. “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, live mannequins at Ridgefield Conservatory of Dance, musical performances on the library lawn, and breakfast with Santa on Saturday morning at the Boys and Girls Club.

Ugly sweaters

New this year will be an ugly sweater contest and a selfie scavenger hunt in downtown Ridgefield.

The scavenger hunt will take place throughout the weekend and will task attenders to take pictures of everything from strolling carolers (7 to 9:30 Friday) to toy drive donations (10 to 2 Saturday) to magic shows (1 to 1:45 and 3:15 to 4 Saturday).

The ugly sweater contest will take place between 2 and 3 on Saturday. Judges will be First Selectman Rudy Marconi, artist Tina Sturges, Chris Mann, Dave Schneider (CEO, Fairfield County Bank), comedian Chrstine O’Leary, and interior designer Andrea Romeo. Judging with take place outside of Fairfield County Bank Insurance Services.

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.

“The ugly sweater craze has really taken off,” said Kathy Graham of Fairfield County Bank, who has been organizing the Stroll for the past two decades. “We want to create something that people of all ages could participate in, and we really wanted it to be on Saturday afternoon to encourage shoppers to be in the downtown.”

“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.”

There will be five $100 gift cards to downtown Ridgefield businesses. They will be awarded to ugly sweater contest winners in the following categories: family, child, adult, teenager, and merchant.

Just visit the downtown Ridgefield Facebook page to find and download the form,” Graham said. “All the instructions on how to register are there.”

As for the Holiday Stroll’s scavenger hunt, participants will snap a selfie with their face and the scavenger item and post it to Instagram with #RidgeScavHunt19.

Don’t have an Instagram? Residents can always create an account for the weekend and delete it after the game. Posts must be from the same account to count toward the same person. First and second place winners will receive prizes.

“This is a whole new way of doing a scavenger hunt and we think it’s a great idea,” Graham said. “A little secret to those thinking they can complete it all Friday night: One of the 10 selfie tasks is to get a picture of the magician Tom Pesce. And he’s only performing Saturday this year so it really pays to be in town 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,” Craig said.

“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,” Graham said.


The ugly sweater contest isn’t the only new event 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.

“Not to project but I think this will be very popular,” Craig said. “They’ve recreated the Monopoly board with all things Ridgefield. For anybody who loves this town, you’re going to want to see it.”

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, just walking outside and taking that small break and seeing the mass of people,” he said. “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 that fact. It’s a townwide party and there’s nothing else quite like it.”