Just did my first off-road since...1965. Yep--I'm that old! In the Sonora Desert, Arizona. Summer job with a mineral company in International Scouts (three sticks). The bug never left me. My report here is on my first real rock crawl.
A guy in my neighborhood with a serious off-road Wrangler recommended the "Ma Bell Trail," in Northampton, MA. (May come up on maps as "Florence.") Search 805 Sylvester Road, Northampton/Florence, although #805 couldn't be located by my on-board navigation. It's unmarked, but I found it!
I would describe it as an easy to intermediate rock crawl. If you've done the Gunstock NH OffRoadeo, and have Sasquatch or equivalent lift, you can do this. It's a 1.5 miles, deadend near the top, then descent the same route. Good loose rock to handle, and moderate ledges to creep over. The first rise looks intimidating, but once you get up that you'll feel empowered. (Some lift is helpful but stock Wranglers do it.) It's deciduous woodland, so should be lovely for October foliage.
https://www.where2wheel.com/trails/trail/full/196
The town of Northampton is very eco-sensitive, so be especially careful about landscape preservation and NO LITTER!
Fellow newbies--go for it!