For most who have not been there, Christmas Eve in Woodstock is all about Santa’s arrival, which has taken many wondrous forms over the years. Will he be coming from the sky, down Tinker Street, up over the rooftops – or in some strange fantabulous contraption out of some rock ‘n’ roll stage manager’s fever dream? It hardly matters because those who attend year after year know that the best parts of Christmas Eve are often atmospheric, no matter the weather.
First off, there’s the magic of the Woodstock Village Green in winter, ablaze with shop lights and a magnificently decorated tree and menorah. Then there’s the music, from traditional carolers and brass band offerings, at times, to the ever-present rock bands, with backup singers and horn sections most years.
Of course, Santa hands out stockings to everyone. It’s a mad crush to get to them, but everyone’s friendly and accommodating, which brings up the best of the best: the feeling of both anticipation and tradition, old-style holiday suspension of disbelief and a postmodern hipsterism that allows folk to reminisce about past Santa arrivals and the tricks of the trade and many local personalities behind this evening put on by old rock ‘n’ rollers.
Things kick off around 5 p.m. or so; it’s good to get into town and park a bit early. But in the final round, everyone gets home about 7, flushed and bright-cheeked from the chill, yet aglow with holiday magic.
Join the family! 
