I got to try the biggest paved-road climb in the Hudson valley and it was somewhat interesting. It's from Ellenville up to Cragsmoor (by the southern border of Ulster county on or parallel to Rt 52, can find it on this map (http://maps.google.com/maps/ms?ie=UTF8&hl=en&msa=0&ll=41.72623,-74.152222&spn=1.039263,1.785278&z=9&msid=115487569681665383360.0004500780f0c26f41b8a))
It goes on at least four different roads, so I'm just calling it "Cragsmoor West" -- because Cragsmoor is the named village at the top, but there's another worthy climb to it from a different direction. (somebody else called it "South Gully", but there's no sign out there on the roads with that).

Total climbing is about 1700-1750 vertical feet. (I think the second highest is Sugar Loaf at 1650-1700ft, third is Slide Mt rt 47 at 1450ft ... or perhaps Rt 44 Minnewaska from east side, depending on how choose to count it.)
lots more details about "Cragsmoor West" (http://www.roberts-1.com/bikehudson/r/m/climbs/index.htm#Cragsmoor_West)That page has some others of my favorite climbs in the Hudson valley (also shown on this map (http://maps.google.com/maps/ms?ie=UTF8&hl=en&msa=0&ll=41.72623,-74.152222&spn=1.039263,1.785278&z=9&msid=115487569681665383360.0004500780f0c26f41b8a)). I've been doing climbs up there longer than in New Jersey, but there's so many in southern New York that I'm not going to attempt to make a list ranked by steepness difficulty like I've tried for NJ."Vista Maria" was the climb that got me to come to Cragsmoor that day. Thought I grew up in the Hudson valley and was an officer of a Hudson valley bicycling club for several years, the only way I ever heard of it was on the NYCC website -- thanks to Hank Schiffman for putting it out there (and also the "Cragsmoor West" climb under a different name).

Vista Maria Rd has a very steep section, 450 vertical feet at 14%, and much of that is 16% of more. The whole climb is about 1300 vertical feet together with three other roads, and two of those roads have steep sections of their own.
Toughest in the Hudson valley? Vista Maria is a good candidate -- I'm open to more nominations.
lots more details about "Vista Maria" (http://www.roberts-1.com/bikehudson/r/m/climbs/index.htm#Vista_Maria)
Whoops -- "Cragsmoor West" is not the biggest climb in the Hudson Valley. Turns out that Mt Greylock in northwest Massachusetts is surrounded mostly by land that drains to the Hoosic River, which flows into the Hudson River. The climb on paved roads up the north side of Mt Greylock is almost 2800 vertical feet. So I'd better say, "Cragsmoor West is the biggest climb in the Hudson valley south of Albany".Ken

I have got to make my way up there this summer... that looks like fun. Unless I make an effort to get out of the city for a nice ride the only real hill I regularly tackle is the Queensboro Bridge. I know, it's not that much of a hill, but with a nice headwind and a skull splitting hangover it'll test yer mettle... (yes, I feel better now)

And thanks for all the work you do Ken, your site rocks. I've been using it for years on the few occassions I get to ride further north...

I have got to make my way up there this summer... that looks like fun. Unless I make an effort to get out of the city for a nice ride the only real hill I regularly tackle is the Queensboro Bridge.
Thanks -- I remember last time Sharon and I rode across the Queensboro bridge we were glad we've got some real low gears on our tandem.

But if most of you hill training is on the Queensboro bridge, I'd say don't try either of the climbs I reported. Think about . . .
Bear Mountain -- rewarding views at several points, interesting curves and steepness variations, and much of it is fun as a descent -- and it's in range of the Garrison train station (Metro North) -- and can be combined with some larger tours.

Ken

Here is a difficult route in New Paltz. You can add at least three climbs to this ride--Yagersville, South Gully, and Glade--to make it a death ride. http://trail.motionbased.com/trail/activity/6074956

Nice! Thanks Ken. Very informative & detailed. I'll have to try to ride both of those climbs this summer, along with the Devil's Kitchen.

I've gone down Vista Maria and that descent down into Ellenville. One helluva glide, however, going down the road is somewhat patchy at times so you can't just bomb it. Once you hit SR52 though, that is paved and a nice fast descent into downtown Ellenville.

Jay