We're looking for an overnight loop near the Boston area. I've checked out the Pemi Loop Hike in New Hampshire, but it's strenuous and we think it might be a little too much for the more novice members in my party. We have 3 days off in November. The Pemi Loop takes 3-4 days, so even if we chose it, it might be pushing it. Any other recommendations?

EDIT I meant that we are from Boston and are willing to drive up to 3 hours away to hike. We have done plenty of day hikes that distance away. I've hiked Mount Monadnock with this same group and we thought it was good terrain for our skill level. So something like that for a few days would be ideal.

We all have a 3 day weekend in November off, so we thought it would be fun to try an overnight.

None of us have hiked overnight before, so I'm not too familiar with how campsites work. I'm guessing it varies a lot depending on the trail. But if I can get any and all suggestions for 2-3 day loops in New England, that would help greatly. Then I can start looking into details and finding the right hike for us.

Also, it doesn't have to be a loop. As long as I can get back to my car to drive us home that works.

  • Hi! I see you've been around the network for some years but this is your first post here, so, welcome! Commented Oct 18, 2017 at 2:53
  • How near is "near"? If by "Pemi" (no, not gonna follow a link to get essential information on the question) you mean the Pemigewasset Wilderness, then that's not near Boston, else you would have asked about New England. Commented Oct 18, 2017 at 10:57
  • Oops. Sorry. I guess the Boston part was misleading. Ill update the question with many more details.
    – honestemu3
    Commented Oct 18, 2017 at 15:44

1 Answer 1


There isn't a lot of wilderness near Boston, but there are many local trails. Camping is not allowed on most land that local trails pass over. However, it is sometimes possible to get permission. It is probably possible to string together a loop on local trails with pre-arranged camping permission in specific areas. You would have to do a lot of digging to find the many local trails, find a decent sized loop, then look for camping permission at a few selected sites along that loop.

If you are willing to spot a car instead of requiring a loop, then you have many more options. There are more regional trails in the area than most people realize. These are long enough for 3 days of hiking. The closest such trail to Boston is probably the Bay Circuit Trail, which runs through 37 towns in Eastern Massachusetts. I don't know what camping restrictions there might be, but I'd start out assuming camping is not allowed without specific permission that needs to be obtained in advance.

For a littler further from Boston but a more wild experience, check out the M+M, and Midstate Trails.

If you are willing to get further from Boston such that the question is really about New England, then there are many more options. These include the Berkshires in western MA, the Green Mountains in VT, the White Mountains in NH, and many other more wild areas than anything near Boston.

  • Are there possibly (private or public) campgrounds around? European long-distance hiking trails within countries like Germany and France pass through many towns, so may be comparable to the more densely populated areas of New England, but they also pass near many private campgrounds where of course anyone is free to approach, camp, and pay for it, provided they have place (no problem in November) and open (may be a problem in November). I'd have no doubts recommend that in France or Germany but I don't know enough about New England to know if this is feasible.
    – gerrit
    Commented Oct 19, 2017 at 0:04
  • @gerrit: There may be a few private campgrounds around, but these are sparse in populated areas like around Boston. The local trails around Boston are used for day hiking. There is no infrastructure specifically set up to accommodate over-night hikers. In the more rural areas like the M+M and Midstate Trails pass thru, there are many spots in the woods suitable for backpack camping. Whether that is allowed is a completely different matter. 3 hours north of Boston in the White Mts, backpacking is common, and there is infrastructure to support it in some places. Commented Oct 20, 2017 at 11:28

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