…Assuming I was using a “smallish” boat, of course. Like “life raft” small, if need be.
Having lived in California all my life, I have to admit my ignorance about the geography of New York’s waterways. And my old warhorse atlas hasn’t been as much help as I’d hoped it would.
So…can anyone help?
You could come pretty close, a little south of Sauerties you would hit glenerie falls which would most likely be the end of your trip. about 1 to 2 miles away.
But then again I have heard some talk about taking a jet ski to Hunter Mountain in the summer - but just talk and after a great many beers.
You can sail quite a large boat up the Hudson River, say to the town of Catskill. Does that count as “into the Catskills?”
If you want to get nearer to the hills/mountains of that name, you could take your raft up the Esopus river. There is at least one dam to get past (right in the town of Saugerties) but it quickly becomes very scenic.
I think you can (unless you hit falls or other barriers), but don’t go via the Hudson. Go up the Delaware River.
I was checking out the Delaware when stuyguy posted. From the Delaware Bay, up the river to Hanock, NY, then the East Branch to East Branch, NY, then Beaver Kill until you run out of water. Unfortunately, I have not been able to pin down just where you’d run out of water.
Alternatively, do take the Hudson, but go all the way up to the Mohawk at Albany, then west to the Schoharie Creek and South to the Schoharie Reservoir just South of Gilboa.
(If you consider portaging acceptable, then the East Branch (past the Downsville Dam and Pepacton Reservoir) and West Branch (past the Cannonsville Reservoir) of the Delaware River, as well as Schoharie Creek (past the Schoharie Reservoir), will take you well into the Catskills.)
Back in the colonial days, people used to sail from New York to Albany and back, and there are still plenty of boats to be seen on the route. As the Catskills are a bit further south than Albany, I can’t see why you couldn’t do so yourself, although I’ll admit to not being familiar with the Hudson River itself, only its eastern banks.
Historically speaking, men used to bring their trappings to the coast via canoes from the Catskills. Makes sense if man hasn’t screwed up the waterways we could get back.
this site might help… 
I used to have a lightweight aluminum canoe w/ a mini 5hp outboard that was excellent for upstream adventures. Most of the time it was just my brother and I. We’d take a couple of paddles, fishing equip. and a few camping items (save the motor for emergency ie: injury or necessity ie: getting out of storms/rough or fast water).
A good new lightweight five horse outboard motor will get a canoe back downstream in a hurry. Take an extra can of gas if your gonna be far in between supplies. Twenty or thirty miles at a stretch should be the most you’d want to isolate yourself. That’s a couple of days upstream paddling easy, fishin, sightseeing, eat, camp etc. (depending on the current of course). Unless you’re experienced, then I’ll shut the f…up.
20 miles is a long way if your in a hurry.
We’d often stay gone for days. One time we went camping and were gone all spring.
Of course you may be in a hurry and have a rig that’ll get ya there quick. Oh, yeah you were talking bout a raft. :smack:
anyway
Had some damned fine times. 
Sorry ‘bout the hijack, just remembering some good ol’ days.
Danke shoen, all!