Holiday Stroll kicks off Friday

Ridgefield’s annual Holiday Stroll will light up the village business district Friday night, Nov. 30, from 6 to 10 p.m. and Saturday, Dec. 1, from 10 a.m. to 7 p.m.

“On Friday, people come into town and make their shopping list; and, on Saturday, they come back and do their buying,” said Bill Craig of Craig’s Fine Jewelry, a founder of the Downtown Ridgefield merchants association that sponsors the 19-year-old event. “It’s a little less crowded on Saturday so people like to take advantage of that and the extended store hours.”

The Stroll used to stop around 4 p.m. Saturday but has had extended hours over the last several years to give shoppers the opportunity to come back with their wish lists and buy presents.

“The crowds are so big Friday, and the event that night is so popular, that we felt we really wanted to increase the level of activities on Saturday,” Craig said.

That’s why residents will see real-life toy soldiers strolling the village late Saturday afternoon, from 4 to 7 p.m., this year — a tradition that began on Friday night and has carried over into a two-day celebration.

“We’ll also have ice sculptures of characters from the Grinch in front of town hall Saturday so people can come and take photos with those,” said Kathy Graham of Fairfield County Bank, who organizes the event every year.

Of course, Friday will still have plenty of fun.

The traditional horse-drawn carriage rides will be back, carrying residents and visitors alike from the Ridgefield Library to the Lounsbury House and giving them a full Main Street experience.

Also returning are the strolling carolers on Main Street, magician Tom Pesce in town hall, RMAC and Cheese at the library, the world-famous ice sculpting event on the green outside Prime Burger and the Ridgefield Lions Club will be hosting a postcards for the troops event at Lounsbury House — all taking place Friday night.

“Friday night is the biggest, but we’re always trying to make Saturday bigger and attract shoppers to our wonderful town,” said Graham.

The Stroll is in fact so popular it may attract Hollywood cameras this year.
“It’s rumored that a movie production company might be there Friday night,” Graham said. “The scene will make it into a holiday movie next year on the Hallmark Channel ... We don’t know for sure if they’ll be here or not though.”

Saturday is for Santa

The Saturday festivities begin with “A Pancake Breakfast at Santa’s Workshop” from 8 a.m. to noon at the Boys & Girls Club.  

While the Stroll is entirely free, breakfast with Santa does come at a cost — $8 per adult, $6 per child ($30 max per family); — tickets may be purchased in advance at the club all morning long or by calling 203-438-8821. Online registration can be done at

The fun-filled event includes holiday games, arts and crafts, letters to Santa, Amber Alert registration (by the Ridgefield Rotary), Christmas wish lists, holiday cookie decorating, and photos with Santa.

Back up Main Street, there will be no shortage of activities Saturday, with singing toy soldiers who will invade the village area. There will also be a jewelry-making workshop in the SPHERE storefront on Main Street.

“The toy soldiers are very popular,” Graham said. “We see a lot of families take photos with them and use that as their holiday card picture, and that’s because they’re so festive-looking. They really do look incredible.”

Ridgefielders aren’t the only ones who get in on the strolling fun.

“It’s the biggest retail event that Ridgefield has throughout the year and it has become a tradition for people in town and from all over the area,” Graham said. “Everyone knows about Ridgefield’s holiday stroll — it’s a fun event that kicks off the holiday season. Lots of families have visitors come from out of town to celebrate it. It’s incorporated as part of their holiday tradition.”

Rain or shine

Just how many come to town each year?

“It’s hard to know,” Craig admits. “We should have a counter one year.”

Graham estimates that it’s thousands.

“There’s never much room on the sidewalks — the streets are packed,” she said.

The Stroll’s Facebook page has been liked by more than 68,300 people, according to Craig.   

“It is like the movie Field of Dreams,” he said, “build it, and they will come.”

Of course, weather is the variable Craig and Graham still can’t control after all these years of planning.

“It’s going to happen,” said Craig, “rain or shine.”

Regardless of what hand Mother Nature deals Ridgefield, the Stroll continues on.

“It’s amazing to see how packed it can get even in the years when we don’t have the best weather,” Craig added.

“Credit to the police, they make it run smoothly no matter what happens with the weather.”

The shape of ice

While the horse-drawn carriage rides are the biggest draw every year, Graham said, world-famous ice sculptor Bill Covitz always brings a huge crowd.

“Bill will be carving out the Grinch sitting on a park bench made of ice,” Graham said. “People can sit next to the Grinch and have their photo taken.”

The other main attraction is the music.

“The sights, the sounds, the extravaganza,” said Graham. “That’s the wonder of it all.”

“It’s a great kick-off to the holiday season, and it’s an amazing time for residents to discover everything Ridgefield has to offer,” she added. “The atmosphere, with all the lights on and the people laughing having a good time, is picturesque.”

Just like the fireworks in July, the Stroll is something everybody can set their watches around.

“I can’t believe it’s our 19th year,” said Craig. “It’s just a great tradition — hard to imagine Ridgefield without it.”

“We never envisioned this event to turn into something so popular,” Graham added. “It’s nice to see it evolve and be embraced the way it has been over the years.”