By Rachel Louchen The Rural Intelligence region is never short on things to do. But come the holidays, each weekend is packed with festivals, strolls, bazaars, parties and performances that have become beloved traditions. While some of these holiday happenings are fairly new, many of them have been going on for decades and it could hardly be the holiday season without them. Here are some of the most anticipated and celebrated traditions that evoke the holiday spirit year after year. Litchfield County
Photo: Lyn Stirnweis
Kent Holly DaysNovember 28 – January 4Kent Holly Days begins with a champagne stroll on November 28, but then keeps the holiday spirit running with a month of events. There is the nightly brass band and hot chocolate society, book signings, trunk shows, and the gingerbread contest, which is serious business. A highlight of the month-long Holly Days is the Kent Historical Society's Colonial Christmas Celebration and the complimentary horse-drawn carriage rides from Kent Greenhouse.
New Preston Winter StrollSaturday, December 6, 3 - 6 p.m.The entire charming Village of New Preston really lights up for the season when each storefront is ornately and beautifully decorated with festive lights and creative window displays. Inside, proprietors hand out complimentary drinks and treats amidst live music. The sixth-annual stroll is also unique because the entire town is pedestrian friendly; most of the antiques, clothing, home design, and book stores are all within walking distance to each other.
Photo: Don Perdue
Nutmeg's Nutcracker, TorringtonSaturday, December 6, 2 p.m. & 7 p.m.; Sunday, December 2, 7 p.m. One of the longest regional traditions is Nutmeg Ballet's Nutcracker at the Warner Theatre in Torrington, now in its 45th year. The entire town looks forward to The Nutcracker’s return and the high-caliber performances by the ballet company, so it's not unusual for attendees to attend multiple performances. Audiences of all ages will be delighted as they are whisked away on a magical Christmas journey through the Land of the Sugar Plum Fairies. Dutchess County
Parade of Lights in Pine PlainsSaturday, November 29, 5 p.m.If you’re going to wait out in the cold for a parade, it better be worth it, and the Pine Plains Parade of Lights does not disappoint. The 29th annual celebration begins with a day of events that includes decorating the town's tree and a visit from Santa and Mrs. Claus prior to the parade. The procession of cars and floats are, true to its name, all decked out with lights that set the entire hamlet aglow.
Sinterklaas, RhinebeckSaturday, December 6, 10 a.m. - 10 p.m.Sinterklaas is an extremely old tradition, dating back 300 years in the Netherlands. But it has a very modern presence in Rhinebeck, with a day-long, town-wide celebration of performances and open houses. Events include live music, dancing, theater, puppet shows and storytelling followed, at dusk, by a starlight parade, plus food and drink and a late-night party for adults.
Columbia County
Hudson Winter WalkSaturday, December 6, 5 - 8 p.m.The words "cheerful" and "hip" seldom figure in the same sentence, much less one that's about the holidays. Yet, somehow, Hudson's Winter Walk is both. There is the Santa parade, street musicians, fireworks, and people in costume, and shops and restaurants turn into warm and welcoming havens. Fireworks launched over Warren Street conclude the festivities, but many of the shops and restaurants stay open late.
Berkshire County
It's A Wonderful Life at Shakespeare & CompanyDecember 5 – 28We consider It's A Wonderful Life required viewing during the holiday season. Shakespeare & Company has taken a cue and hosts a live radio show, where the story of George Bailey and the angel Clarence come alive on stage. The production was so successful when it premiered last year that it returns this winter and just may become a longtime tradition, much like watching the film has been to so many generations.
Stockbridge Main Street at ChristmasFriday, December 5 - Sunday, December 7 Dreaming of an idyllic New England Christmas? The Stockbridge Chamber of Commerce offers one that's straight out of a Norman Rockwell painting. Literally. For the past 25 years, the organizers have gone to great lengths to create a tableau vivant of Norman Rockwell's iconic painting, "Stockbridge Main Street at Christmas". Same decorations, same vintage cars — the only difference in the recreation is that the Red Lion Inn is all lit up; when Rockwell did his study, it was closed for the winter.
Williamstown Holiday WalkSaturday, December 6, 3 - 6 p.m.Williamstown decks the halls for its 31st annual Holiday Walk. The event has an old-fashioned New England feel to it with caroling and horse-drawn carriages, and classic events like visits from Santa and the live reading of A Christmas Carol. Don't miss Saturday's Reindog Parade, when dozens of family pets are dressed up as, you guessed it, Santa's faithful animal sidekick.
Photo: Joanna Geige
Great Barrington Holiday StrollSaturday, December 13, 3 - 7:30 p.m. The 6th annual Southern Berkshire Chamber of Commerce's Holiday Stroll is the chamber’s largest community event, often attracting more than 3,000 attendees. This year features 50 food and product vendors, crafts, music, caroling, face painting, live window displays, a character parade, hayrides, and gifts to the kids from Santa Claus. The evening ends with a spectacular fireworks show that rivals any held on the Fourth of July.
