5 of the Best Hikes in New England

If you know anything about my hiking style you know that if I hear about a trail that is less traveled then I’m going to be instantly drawn to it. Whether it’s a day hike or a backpacking trip, the more remote the better, in my opinion. So when I stumbled upon the myriad of short long trails that are scattered throughout New England and are less-known I was instantly intrigued. While I’ve spent the last few years focused on hiking the White Mountain Guide, prior to that I had tackled a few of these short long trails and this spring I am stoked to take on a few more. These trails are all hikes that can be done in less than 5 days, and whether you’re planning on doing them as backpacking trips or day hikes in segments, you will not be disappointed. So without further ado, let’s get into the hikes!

1. The Wapack Trail

This 21 mile trail runs from the north side of North Pack Monadnock to the southern trailhead on Mount Watatic in Massachusetts. Running over the summit of a half dozen named peaks all under 2,300’ high, do not underestimate the difficulty of this traverse. Whether you’re looking to set out on an overnight or want to take on all 21 miles in a single day, this hike will leave you feeling accomplished. Overall elevation gain hits above 5,000’ regardless of which direction you go. I have hiked this trail twice and both times I went southbound, completing the hike in a day. If you choose to complete this as an overnight, you will want to book camping ahead of time at either the shelter on trail, Windblown Camping, or at a local hotel or state park. The beauty of this trail is that it can be hiked much earlier in the season because it is located in southern New Hampshire. Furthermore, if you choose, you can connect to the Midstate Trail prior to the summit of Mount Watatic and continue hiking right down into Massachusetts. Find more information on the Wapack Trail website.

2. The Metacomet-Monadnock Trail (New Hampshire)

The Metcomet-Monadnock Trail in New Hampshire has an interesting history. Originally, when developing the New England Trail, the plan was to continue the trail through New Hampshire, and the Metacomet-Monadnock Trail is a remnant of this plan that fell through. Running at 18 miles (not including the approach trail on Mount Monadnock), this trail is a lot more rugged and harder to follow than all of the other trails in this article. From the summit of Mount Monadnock, the trail runs south into Massachusetts where it ends on a dirt road. Taking you through a series of hardwood and softwood forests, and over the summit of a few smaller mountains, as well as to the summit of Mount Monadnock, this trail gains over 5,000’ of elevation. There is a town along the trail where you can stop for snacks and a half mile from the trail in the town of Troy, New Hampshire, there is the option to tent at the Troy Tent Site. If you continue straight past the southern terminus you will connect to the New England Trail and can continue your journey south into Connecticut. Or, if you’re going northbound you can continue from the summit of Mount Monadnock onto the next trail I want to talk about: the Monadnock-Sunapee Greenway. Find more information on the Metacomet-Monadnock Trail website.

3. The Monadnock-Sunapee Greenway

The Monadnock-Sunapee Greenway is a trail that I have hiked twice now, and in 2019, it was the first overnight hike that I ever did. Running 48 miles in length, not including the two approach trails, this hike is the perfect shakedown hike to do before a longer thru-hike. Once referred to as a mini Appalachian Trail, the Monadnock-Sunapee Greenway even has a town stop with a convenience store that caters to hikers, an end-to-end patch you can add to your collection upon completion, and several shelters along the trail. This trail is located in southern New Hampshire and runs from the summit of Mount Monadnock to the summit of Sunapee Mountain. It is a great hike to do in shoulder seasons when you’re waiting for the snow to melt in late April or in fall. Rather than going into all the details again, I’m going to direct you to the post that I wrote last year: The Backpacking Trip You Need to Add to Your Bucketlist: The Monadnock-Sunapee Greenway

4. The Tully Loop

This loop hike is located in north-central Massachusetts and runs 22 miles in length. The perfect overnight, I’ve done this hike twice and backpacked it once. The Tully Trail coincides with the New England Trail for a small section. The beautiful four-sided shelter at Royalston Falls sits right along the trail and is the perfect spot to spend the night. Furthermore, this trail winds through stunning hardwood forests on Tully Mountain and along the edges of Tully Lake. This hike gains over 3,900’ of elevation regardless of which way you go. Parking is available at the Tully Lake Campground which is where I started and ended my hike. The Tully Trail is very well maintained and easy to follow. 

5. The Grafton Loop (West Branch)

The Grafton Trail is located in Grafton Notch, Maine. I have backpacked the western half of this loop hike twice now and although there is the option to complete the 36 mile loop instead of only completing one half of the trail, so far I’ve only done the western side. This section of the Grafton Loop is 15 miles long and gains over 4,800’ southbound or 5,600’ northbound. The western branch of the Grafton Trail coincides with the Appalachian Trail from the trailhead in Grafton Notch before branching off on the summit of Old Speck Mountain where the AT runs south. After reaching the summit of Old Speck, the Grafton Trail continues down into the wilderness and seemingly away from civilization. There are four maintained tent sites available along the trail. There are no bailout options along the trail once you pass the Appalachian Trail, so know that once you enter this section of trail you’re more or less committed. An unofficial herdpath is marked with a cairn in Miles Notch and this could serve as a bailout if needed however this is still halfway through the hike. The trail is rugged, remote, and while maintenance has been done in recent years, there are still some pretty overgrown areas on the trail which can be difficult to navigate for some.

At a Glance: New England's Top Short Long Trails

Additional Short Long Trails of Note

This spring and summer I am planning on hiking a few additional short long trails that are located in New Hampshire. The 50 mile Wantastiquet-Monadnock Trail, 75 mile Sunapee-Kearsarge-Ragged-Greenway, and the eastern section of the Grafton Loop are on my radar for the 2024 hiking season.