Planning on a trip up to Poughkeepsie for parents weekend visit to Marist College - but not very interested in what the college has planned for tours. (Coming from Long Island, have own car)

So we were planning on going into Rhinebeck, but just read that it is the same weekend as the Rhinebeck Fall Festival.

How crowded is the Rhinebeck Fall Festival?

How is the parking in the area?

How crowded do the streets in town get from the spill over from the fair?

Love the idea of Rhinebeck's Town, but not lovers of crazy big festivals, we're more of a smaller fair kind of people.

Should we skip the fair and try to get into FDR's Home or the Vanderbuilt instead? I was planning on only doing that this time if it were raining!

Thinking of the restaurant GiGi's or Double O Grill - which would be better for 2 women and 2 Freshman Students?

Any thoughts, Ideas or suggestions - Welcome!

Is this the crafts fair? I've been to one there in the summer, but the bigger crowd seems to be in August when they have a county fair.
The fairgrounds are actually sort of walkable from town, so you can consider that option too.
It is a big sprawling fairground, so I never found the fairs themselves that crazy crowded. Frankly a fall weekend is going to be really busy anywhere in Dutchess county--all the mansions, towns, fairs, so just pick what seems most enjoyable to you and go!

If you're talking about the Rhinebeck Crafts Fair, it's a big one, but it really doesn't impact that much on the downtown area.
I'll have to disagree with the previous poster. The fair really isn't that walkable from the center of town. However, it is worth going to, as it's probably the best one of its kind in the area.

Vanderbilt is quite nice, worth an hour's stroll or whatever.

You're smart to get out of Poughkeepsie. I grew up there; it's not very appealing. (Marist is a very nice campus, however.)

Gigi's is v. good; haven't been to Double O Grill. Street parking in Rhinebeck is decent, tho I have no idea what it's like during a fair.

Well Howard, I did say "sort of walkable"
I've done it. From Beekman Arms to the fairgrounds is probably about a mile?mile and a half? I'm a NY city girl and 20-30 blocks counts as walkable to me. There are sidewalks much of the way, so it's not like walking a suburban road.I didn't want to deal with getting a car in and out of the parking area when I went to the county fair a few years ago, and the weather was nice that day, so walk I did.

janie, I'm a walker, too....but think it's a bit much to walk, especially since you have to do a lot of walking once you're at the fair!
Anyway, it's

Oops, pressed the wrong button! As I was saying.....It's a marvelous fair and the OP should go.....along with seeing the Vanderbilt Mansion and FDR's home and museum.

I love Fodor's! In 1 hour got reply's to my request for information. Thanks! to you both!

The Rhinebeck Crafts fair is one of our favorites. It's a big property (self contained)so it does not get too crowded. It's worth going to if you like crafts. The town doesn't really get a bit "overflow" from the fair.

Last time we were in the area (August) we ate in a new restaurant - Shadows on the Hudson in Poughkeepsie. Very good and reasonable, nice water views.

The Vanderbilt and FDR mansions are both worth visiting if you've never been. There's also the Wilderstein mansion (FDR's "girlfriend").

Have fun!