What's the most fun town activity that happens in Rhinebeck annually?

Sinterklaas is a great event in Rhinebeck each year. Activities have already begun and Sinterklaas "arrives" by boat in Rhinecliff on Sat, Nov 24th. The actual Sinterklaas celebration is on Dec 1st. Rhinebeck will close Market St between Rte 9 and the municipal parking lot to allow for a safe, pedestrian experience in the village. It runs all day and culminates with a parade. More information can be found at www.SinterklaasRhinebeck.com or search Sinterklaas Rhinebeck on Facebook for schedules and details.

Anjanette had pretty much all my answers for fun stuff to do in Rhinebeck, but one she didn't mention is the Sheep and Wool Festival, which is quite a bit of fun, and I believe it's every October, or at least every fall.

Well, there's quite a few fun activities, actually. Every year (now going into year thirteen) there is the amazing Woodstock Film Festival. Although it centers in Woodstock itself, there are events and screenings in Rhinebeck and other area towns. There are also a plethora of chocolate tastings at Oliver Kita Chocolates. There is a Bark-a-thon in August. There is a "Sassy Senior Fashion Show" at Arbor Ridge. And, there is an artists for autism benefit concert.