Entry-level mountaineering - Catskills, Adirondacks, or anywhere else nearby

Thanks, guys.

Jay, I'm definitely not planning on doing anything solo, but thanks for the heads-up. I'm having trouble finding information on Black Mountain winter ascents. Would you be able to point me in the right direction, or give me a little more info as to what it would entail in terms of what I've been posting until now? Specifically when I should go to give me the best chance of finding what I'm looking for, and what gear I should bring. I did find this, though: peakbagger.com/peak.aspx?pi…
is the route you're thinking the one marked after the south margin, or the more prominent gully further north?

Thanks again, everyone. Really appreciate it.

Ah, found it. This quote stolen from Jason Brechko, who masterminded the crazy scheme to climb up Black this way:

Black Mountain Gully: 700', NEI 2-3+ Jason Brechko, Andrew Brechko 1/21/12

When viewed from Bolton a steep gully can be seen bisecting the west face of Black Mountain. Climbing it is more of an adventure in route finding and back country travel than a steep ice climb but is a fun adventure none the less with spectacular views of the narrows and the tongue mountain range.

Park at the Black Mountain trailhead. Hike into Black Mountain Ponds and after the last pond where the trial intersects the lake trail that climbs Black's SW ridge, continue heading NW trending slightly down hill. Keep an eye up slope until you can see both sides of the steep forested gully high above you. Hike to the stream in the north side of the gully about half way up the mountain. Head up to the first ice and follow the stream bed through a few tiers of grade 2-3 ice bisected by fairly long walking sections. Finally you will end up a NEI2 flow a couple hundred feet tall with steeper finishes possible. From here the gully narrows. Exit onto the north ridge of the gully via a left facing corner right of a brushy slab. Follow the ridge up till you see a cliff band with steep 50' flows. A fat and beautiful 3+ pillar will lead you to the summit plateau and spectacular views. Continue NE to find the trail which you can follow tot he summit and back to the parking lot.