So my wife and I are interested in relocating to a homesteading property in 3-5 years. We're looking at a few parts of the country, but New England has a lot of appeal for us. Originally we were hoping to take over a family farm in Michigan, but the more details I learn, the situation clearly isn't going to work. Edit 3-18-15: spoke too soon. Maybe it will work. It's at least still on the table. So instead we were thinking of tacking a few days onto our summer trip to Baltimore.
Not a lot of time to explore, but any places in, say, Vermont/New Hampshire/Maine that would give us a good sense of the area? Rural but not super remote, as she will need to work full-time for quite a while after relocating and neither of us wants her to have a monster commute.
I know that's a very vague prompt, but Mustachians go!
So you want to visit someplace nice, with an eye to living there? This is mostly a function of what sort of job your wife would be doing, as you aren't going to find too many high tech or biotech firms in the rural areas.
Most inland lots in Maine that are away from lakes are inexpensive. All of Maine is pretty, wooded, rolling hills. Be aware that Maine has an income tax and sales tax, and unlike Massachusetts, they have relatively few services. The areas closer to Boston are a little more expensive and the drive into Boston will be crazy.
Southern NH is a good compromise on distance to Boston vs price, but NH has very expensive property taxes since they don't have an (earned) income tax. Southern NH (and SW Maine) is more exurban than rural nowadays. The rush hour traffic can be horrendous to Boston. (And if you're homesteading without an income, you'll still have a high tax burden, and if you're living off interest and dividends, NH taxes those.)
Vermont is not bad either, and the people there are different, a little more friendly than NH and Maine. Taxes are more like MA and Maine. You'll have to find someplace near a city to work at though. The commute traffic is not bad.
Northern VT, NH, and ME is for the most part relatively less well off, it's more rural, and land is much less expensive.
If I were you, I'd visit the NH White Mountains and Lakes region, maybe the Upper Valley. If you can get to the Maine shoreline, try to get to Acadia NP. Visit some of the smaller cities in the region: Lowell, Nashua, Manchester, maybe Portsmouth, Bath, etc... to get an idea of what it might be like to work there. Then plan to rent for a year when/if you move here, to let things settle out while you get a feel for how you two like the area and if the rural north is to your liking.