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You are blessed to live in an overlanders play ground. This site lists every Class VI road. No guarantee any one raod is going to be easy on a given day as conditions change pretty rapidly (and if you want easy generally avoid the stuff around Unity/Claremont at least til the Spring), but...

you're in my neck of the woods. the pilgrimage attracts overlanders and is advertised as an overlanders event is but its rustic lux base camping (ie food trucks) + offroading. its more like a vendor exhibition meets an all-vehicle Jeep Jamboree. they also make up their own trail rating system...

CT is terrible. There's no real overlanding route, no real public trails for whatever version of offroading one may like and certainly no ability to integrate a 4-6 rated trail into an overlanding trip. Primitive camping in CT is no better. Pretty much Nipmuck state forest is it and you need a...

Long time lurkers. We joined to participate in this discussion FWIW. Anyway, we don't think the labels are useful. We came to overlanding / offroading after decades of hiking/climbing/backpacking. In that world the same debates rage about who's "really" doing the sport. Weekend backpackers vs...