The holidays are upon us, and once again, Chappaqua is ready. After the turkey has been served, Friday, November 28th sees the sun go down, and with the community gathered, the town’s 30-foot tree takes centerstage to kick off the season.
Once the switch is flipped, said Georgia Frasch, former President of the New Castle Historical Society. “There’s lots of oohs and aahhs. People clap and the kids all come and meet Santa.”
Candy canes in hand, the kids don’t shy away from Santa’s cheer and adding Horace Greeley students who lead the caroling makes the evening even more festive. “It’s really sweet,” boasted Frasch.
For the last four years, the Horace Greeley House has hosted an annual toy train exhibit. Opening on November 22nd, the 10 AM – 4:00 PM weekend showings are pretty down home, according to Historical Director, Mia Michelson-Bartlett. “It’s a charming little experience,” she assured.
The staff takes several weeks to set up, and families go from room to room to view. Six or seven runs are being prepared and will include LEGO Around the World, the Polar Express and Santa’s Holiday Train.
Kids aren’t the only ones who are eager to get all aboard. An older generation appreciates the exhibit, too. “They are grandparents who remember playing with trains from their childhood,” explained Frasch.
Even so, they may still need a history lesson, and the Historical Society delivers. “It very quickly transformed the town,” said Michelson-Bartlett of the 1846 construction of the New York and Harlem River Railroad which extended from the city into Westchester as far as Chappaqua. The main factor involved farming. “You could export your goods to New York City very quickly, and keep them fresh,” she explained.
The sea change then centralized the town. “The area around the train built up, and new businesses opened to service the folks coming in,” Michelson-Bartlett revealed.
It doesn’t get too heavy, though. “There are larger train shows, but for families with young kids, I would call this a little more bite sized,” she added.
Alongside the grandeur of the Victorian house and the holiday decorations, the on-time tickets leave kids with their mouths gaping. The villages, the mountains and all the beautiful little lights, she said, “The children are in awe.”
And to make up for the non-hands-on aspect of the delicate exhibit, the society provides a touch room where the kids can play with toys and trains and take a photo while sitting on a mini train.
Parents need some playtime, too. December 5th gives mom and dad the chance to unwind, socialize, shop, and sip wine.
Wine Around Town, puts the locomotion in the soles of Chappaqua resident’s feet and makes the most of the local feeling. “It’s a nice time to sip and stroll,” said Linda Bosco, Chappaqua Chamber of Commerce member. “People go from store to store, bring their friends, and every store has a different promotion. It’s a really great night,” said Bosco.
Then Desires By Mikolay’s Winter Wonderland comes as close as possible to making sparks fly. “They really cut up the ice, so it looks like it’s snowing,” described Tara Mikolay, owner of the high-end jewelry store, where the annual ice sculpting takes place.
A 45-minute process, a sleight of hand that puts pulling a rabbit out of a hat to shame. “It’s really kind of cool to see something turn from a block of ice into something magical,” she added. “The sculpture really textures the spirit of the season”.
Of course, Santa will be there with hot chocolate, but kids won’t be the only grateful ones. “It’s our way of saying thank you to the community,” said Mikolay.
Finally on December 14th, Chabad of Bedford joins in and lights the Menorah at the Community Center. Arts and crafts will be part of the program, but the gathering is more of a religious celebration, according to Frasch.
However, no credentials will be checked. “All are welcome,” Frasch added.
Together, these moments create a season of celebration Chappaqua treasures now and will for years to come.
Explore Special Promotions at Desires by Mikolay
The 5TH Annual Wine Around Town, sponsored by the Chappaqua Millwood Chamber of Commerce will be on Friday, December 3, 2021 from 5-8 PM, it was announced today. 
The holiday season is upon us and it’s time to shop, plan celebrations and also enjoy all our communities have to offer at this special time. Here are a few ideas to help celebrate and enjoy the season all while having fun locally:
5. Enjoy a screening of a Big Band Holiday program from Jazz at Lincoln Center in the New Castle Town Hall Assembly Room. The program runs from 6:30-9, p.m. Friday, Dec. 6 starting with refreshments provided by the Friends of the Chappaqua Library and will feature songs both “sacred and secular.”
8. Why not spend some time in early December learning about the traditions of various cultures, communities and religions? Besides boasting many resources for learning about Christmas and Chanukah, the North Castle Public Library has several books about Kwanzaa (Dec. 26-Jan. 1) and a CD of Kwanzaa music for loan. The Chappaqua Library also offers a book about the Hindu festival of Diwali (this year, celebrated already in October), titles about Chinese New Year, and more.
9. To offset the effects of kugel and cookies, give snowshoeing a try. Skip Beitzel, owner of Hickory & Tweed in Armonk, said “Snowshoeing is great. My adage for snowshoeing is, ‘snow and they will go.’” Beitzel, whose shop sells snowshoes for all ages, said his customers snowshoe on local golf courses or on the bike path that runs through Millwood. Those seeking a more arduous experience may even take their snowshoes to ski areas to use them when climbing uphill. “Why not snowshoe as a family?” Beitzel said, since after all many families ski together, and snowshoeing can be done easily and locally–providing there’s snow.
The Chappaqua Orchestra Concert and Tree Lighting at the Greeley House are a time-honored tradition in New Castle that take place the first weekend in December. This year, however: “We’re kicking things up a notch,” confirmed Leslie Weissman, co-founder with Peg Kafka-Sackler of The Northern Westchester Artists Guild (NWAG), a not for profit consortium of some 75 area artists. NWAG took the initiative to spearhead Holidays Around Town and the plans are as follows: