Getting ready for Santa’s arrival in Woodstock

(Photo by Dion Ogust)

Who is more amped up about Santa’s arrival on the Village Green in Woodstock on Monday, December 24: our children or the Big Kids – the Mamas and Papas and shopkeepers and dedicated town officials who put the whole shebang together each year? Some locals, along with the insiders who design and build Santa’s means of arrival, have lifelong memories of the annual event. It’s been happening since 1932. And with each year, the suspense rises to a pitch as a crowd of thousands waits in the streets.

It’s that matter of conveyance. In the past, Santa has swooped into town on a magic carpet, dangled from a spaceship from 100 feet in the air, flown in on a hang glider, jumped out of the chimney of a cottage, dropped out of the bottom of a VW microbus, ridden in on an elephant and been magically shot from a cannon, along with dozens of other surprising means. 

Singer/songwriter Robert Burke Warren remembers that the guy who played Santa for many years was a professional tree arborist who had no fear of heights. “I always felt something could go wrong – like when you take your kids to the circus – but it never did. It’s become a lot more tame,” he says.


Santa’s first foray into the village was much more reasonable. Richard Heppner, Woodstock town historian, wrote about him driving up Mill Hill Road in a truck loaded with goodies for 150 or so Woodstock children. The Great Depression was on. The modest vehicle carrying Santa Claus transported those kids beyond their wildest dreams, no doubt.

Now stockings are stuffed with candy and distributed to more than 1,000 kids. Donations are collected from townsfolk to produce the event, which costs many thousands of dollars. Last year, Lynn Sehweret at the Town Clerk’s office reported that the biggest challenge in pulling all the pieces together is to make it happen at exactly that right hour. “It starts early in October, when a mailing goes out for donations; the event is totally funded by donations. After that, we have to put together lists for people to get the contents for the stockings and the cheer and food baskets. We get phone calls suggesting that someone might need cheering up or has had some economic downturn and might need a food basket.” It’s a communitywide effort.

As always, the weather is a tenuous variable. Will it snow? Will the temperature drop into the teens and scare people away? Typically, folks show up early to park and walk to the Village Green. All traffic nearby stops at 5 p.m. so that villagers and visitors can congregate and wait for Santa’s arrival – many thanks to the Woodstock Fire Department for its assistance. And a good crowd creates its own heat and excitement.

It’s all about that shoulder-to-shoulder waiting: Listening in awe to the choir that sings each year on the steps of the Woodstock Reformed Church. Mixing it up in the streets with friends and neighbors and strangers. Holding children on shoulders to see what’s going on. Dropping into village shops to spread the holiday cheer. Wondering how the jolly old man in red might be traveling this year.

And when he does arrive, the climax is palpable. All the behind-the-scenes work, accomplished over the past few months by the Woodstock Christmas Eve Committee, culminates in joy and giving and a lot of celebratory folderol. The holiday spirit lives in this Woodstock tradition, for old-timers and newcomers, for the young and the not-so-young.

Meanwhile, back at the Colony, Uncle Rock – a/k/a the aforementioned Warren – will be set to lead a community singalong in his own exuberant style. As soon as Santa shows up and distributes his stockings, Uncle Rock will play a set of holiday tunes, including such rocking favorites as Chuck Berry’s “Run, Run, Rudolph,” the Springsteen arrangement of “Santa Claus is Coming to Town” and Brenda Lee’s “Rocking around the Christmas Tree” and many holiday standards.

After establishing his own tradition of coming to the Village Green on Christmas Eve (even before moving his young family to town in 2002), Warren began performing at the event, one year playing on the flatbed of a truck. “This will be my second year at the Colony, sans the Colony Cats this time. I have an extensive Christmas repertoire, including some that I’ve written. We didn’t know what to expect last year, thinking that parents would just take their kids home after Santa.

“But within a few minutes, the Colony was packed with kids with their parents, grandparents and extended families, and also hipsters and millennials. A few others will be joining me onstage this year: some super-special surprise guests. I feel really fortunate to be part of it. People are ready to sing. It’s a political act with a strong sense of connection and energy. You see so many people that you know. You get to catch up and hang out. It’s the thing I like about living here: the sense of community. It’s rather – very – old-fashioned and heartwarming.”

The Colony’s kitchen and bar will be open, serving hot chocolate, mulled cider and hot toddies. People can drop in and get warm in front of the fireplace before heading home. The doors open at 5 p.m., and the show starts at 6 p.m. The Colony is located at 22 Rock City Road in Woodstock. Admission is by a $10 suggested donation at the door.

Woodstock Christmas Eve/Santa’s Arrival, Monday, December 24, 5 p.m., Village Green, Mill Hill Road/Rock City Road/Tinker Street, Woodstock.