I like Island Pond because it's pretty central. I know others have their own opinion on I.P., but when you stay at the Lakefront for instance, you have a gas station right there, Kingdom Cat across the street, and a couple of resturaunts to eat at. The downside is that on a weekend, the trails in and out of town can get ugly, and then there's Teddy the Constable, Thats a whole other thread in itself. If you like to go fast, and not bother anybody, 102 on the powerline, or the diesel pipeline are good. Anywhere out of the yellow area on the trail map really. We like to ride fast too, but you have to be smart about it. The closer you get to town, the more traffic, so use yer head. And watch out for those moose!!! Nearly had a collision with one last year on 96.
Also, if you do book at the Lakefront, be prepared to part with 90 bucks a night. And that was last years price! Try the Chevy dealer in town. He's got places to stay right there for 30 bucks a guy a night, and he does'nt care how late you "check out" on Sunday.
I'm in Westfield, Mass., and I can get there in three hours.
Good luck this winter, and have fun!!!