I belong to the Hudson Valley chapter, which is the primary driver behind Rhinebeck. I went last year for the first time and have to tell you it's a class act. The Brit bike faction has a strong showing. The Dutchess County fairgrounds are more like a park than a fair ground. It's probably one of the nicest venues for an event I've seen.
The motorcycle timeline is also something originated at Rhinebeck. Last year Frank Westfall riding around on a 1912 Henderson 4. He even had a Henderson mini-bike that somebody built for their kid a long, long time ago.
The meet will also have antique planes from Rhinebeck aerodrome, antique cars, trucks and machinery. The Hell Riders will be there with their Wall of Death. Here's a link to the meet website. http://www.rhinebecknationalmeet.com/index.html The pictures tell the story better than I can.
I don't think you will be disappointed. And there is enough stuff to see and the fairgrounds are so nice that pretty much anyone in the family, whether they are into old bikes or not, will probably enjoy it.
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