Winter Walk Brings Holiday Magic to Hudson

The annual event unites locals for an evening of music, entertainment, and shopping in Columbia County.


Visitors to this weekend’s Winter Walk can expect a family-friendly night of music, performance, and plenty of local charm. Since its modest start as a simple shopping night, Hudson’s largest event has grown all throughout the city, with 20,000 visitors shutting down Warren Street from tip to tail to taste local food, enjoy musical performances, and engage in some charitable giving.

As Executive Director at Hudson Hall, Tambra Dillon is head coordinator of this beloved annual event, but she credits a more diffuse source for its success: “The community,” she explains. “The whole community comes together and makes it happen.”

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Photo by JD Urban


Highlights of 2018’s program include a Bed & Breakfast tour, planned and run by the B&Bs themselves; performances by local musicians, poets, and eccentrics; and a return of Rip the Nut, a piece from choreographer Adam H. Weinart that interpolates Rip Van Winkle’s story into Tchaikovsky’s classic Nutcracker Suite, with both professional dancers and close to a hundred children from Hudson Hall’s after-school programs.

Recurring programs include a meeting with Santa and the beloved window-decorating contest, both of which take place with a particular Hudson charm. “It’s good old-fashioned fun,” says Dillon.

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Photo by JD Urban


When did the winter walk start?

The first Winter Walk was 1997. Our mission is: we’re a cultural organization that’s equally interested in expanding economic opportunity. This organization was conceived to be an anchor in the city that would further the revitalization of Hudson, which, in the 1960s through the 1990s, was in pretty dire shape.

It’s phenomenal what’s happened in the last five to ten years. So they started just on the sidewalks in the two blocks, and it was designed to be a way to animate the streets and do late night shopping and make people feel safe to come back and patronize antique shops and the fledgling shops starting to come back to Warren Street.

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Photo by JD Urban


Are you in charge of planning the performers?

A lot of businesses have their own favorites or people they want to invite, but for other businesses that want to participate, we’ll ask them what they want and then we’ll place a performer with them. The businesses sponsor the performers, and they all get paid.

We’ve hired a young artist to help us reach out to the younger community coming to Hudson now, so we have younger acts and try to keep it fresh and keep it representational.


Photo by Claudia Cinquegrana

Photo by JD Urban


Do you prefer certain kinds of acts?

There’s a lot of music, because that’s easiest for the shops and is conducive to shopping, so that’s everything from contemporary music to classical music to world music. We have flamenco guitarists, harpists, violinists, there are choirs, there are school bands, famous musicians like Ben Folds to unknown students: it’s everything.


Photo by JD Urban


What is your favorite part?

I’ve been to Winter Walk before I started working at Hudson Hall, since 2009 or 2010. My first impression was how delightful it all was. It wasn’t just a generic street fair with another zeppole truck, another tube sock vendor. There are a lot of amateur performers that are so much fun to watch. 

It’s quirky, it’s fun, it’s sincere. It’s fun to walk up and down the street. My favorite part is the window displays. You never know what’s going to happen. The two judges are anonymous, and we allow them to create their own categories, and they’re as creative as the windows! Two years ago the First Presbyterian Church unveiled their restored rose window and got the ‘Jackie O Preservation Prize.’ So there’s usually about a dozen categories that people make up, and it’s fun.

This interview has been edited for concision.

Related: 8 Holiday Festivals to Welcome December This Weekend

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