Best way to enjoy the holiday season in Woodstock

While some folks dread the start of winter, in Woodstock December marks the start of a month of festivities, when the community comes together and we have time to appreciate friends, neighbors and visitors.

The shortened days offer long nights with time to gather in front of a fireplace and either catch up with others or finally enjoy reading that long-anticipated book. And yes, seasonal changes are always reminders about the passing of time, offering a bit of a mental check-in, to review our actions, obligations and align our values.

One of the best community events always happens the first Friday of December – which this year coincides with the actual start of the month. The Woodstock Holiday Open House is a Norman Rockwell-type celebration in the village. Our unique stores are open and serving cider, carolers are found throughout town sharing the joys of the season and most important, good cheer abounds. The festivities start at 4 pm., as dusk settles on the Green, and continue through 8 pm. It’s a perfect time for some shopping, stopping into a restaurant for a warm meal and to just ease into a holiday frame of mind. With so much going on in the world it’s nice to take a few hours and just enjoy a special night.

Entertainment options abound throughout the month. Yes, it’s Woodstock, so of course music is a key component of gatherings. If you want to do some good, and listen to some of the area’s most talented musicians (who happen to be world-renowned) than attend December’s holiday concerts at Levon Helm Studios. Many musicians are performing throughout the month, but “The Sounding Joy: A holiday concert to benefit the Washbourne House” has been a staple of spirit and generosity for more than a decade. This year these concerts are held on the nights of Dec. 15 and Dec. 16. There are different musicians each night, Kate Pierson, Natalie Merchant, Marco Benevento, etc., but always the gathering to support a local shelter for victims of domestic violence leaves people unified in spirit.

For a really special Woodstock event head to the Green on Dec. 24 as Santa makes his annual, albeit not traditional, Christmas Eve Arrival. Forget just reindeer, the man in red hasPeople on the green in snow rushing past stores landed on the Green via elephant , escorted by a jazz band and one year he was even shot in from a cannon. The unconventional arrival, which evolved since an initial Christmas Eve celebration on the Green in 1932 according to the Historical Society of Woodstock is followed with a conventional community  gathering of elves and stocking distribution for children.

New Year’s Eve is always a time of celebration, and while many venues have dinnner specials and live music this year Bearsville Theatre has a wonderful party planned with music and Yellow type explainging a New Years eve party at Bearveill Thetaer, with drinks on the right. celebration. The renovated theater offers an amazing concert experience and it’s a great way to ring out the old and embrace the new – something we do every season, but especially when the calendar reminds us that time is passing.

Remember the Woodstock Inn on the Millstream is always the perfect place to stay whenblue sign covered in snowy branches says Woodstock Inn on the Millstream visiting Woodstock. This December consider upgrading to a fireplace room and  embrace the warmth of making special memories during this holiday season. 

We look forward to hosting you at our little sanctuary in the heart of the Village and if you’d like a personalized room recommendations always feel free to call or text the innkeepers at 845-663-8152. 

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