The Backpacking Trip You Need to Add to Your Bucketlist: The Monadnock-Sunapee Greenway

sockedinhikes Member, Moderator Posts: 22
edited July 2023 in ROUTES & TRAILS

As the northeast settles into the deepest depths of winter I can’t help but feel a little bit nostalgic for the first backpacking trip I ever went on, the Monadnock-Sunapee Greenway Trail. It was 2019, late April, and the snow had finally abated, only to be replaced by a myriad of mud, but I was determined to make the most of my week vacation and was incredibly stir crazy after spending the last few months indoors. I had heard through the grapevine (aka Instagram) about the Monadnock-Sunapee Greenway which was a 48-mile trail running north to south from the summits of Mount Monadnock to Mount Sunapee in southwestern New Hampshire. After purchasing the map and guidebook, a brand new HMG Southwest 40 pack, and several hundred dollars worth of new backpacking gear, I was stoked to take on this mini thru-hike that even comes with a patch upon completion. 

I was more than ambitious in my planned itinerary, thinking it realistic to tackle what would ultimately be 55-miles due to approach trails, in three days, with zero experience backpacking and only having done one 20-mile hike in my life. Needless to say, by the end of the three days I was hurting badly. Despite losing five toenails, this hike will always be one of my all time favorites and after hiking it for the second time in 2021, this time in May, I firmly believe that this is the perfect backpacking trip for those looking to get away for a few days or those who are planning on a thru-hike and looking to shakedown their gear. 

The Route

Both times I hiked the MSG I went from south to north. Starting at the base of one of the most hiked mountains in the world, Mount Monadnock, in Jaffrey, New Hampshire, your hike begins by ascending the mountain from any of the half dozen trails leading to the top, and then descending the northern side on the Dublin Trail to the base, where the MSG heads into the woods. Across a dirt road and directly off of a small parking lot is the first sign that you’re about to step onto a backpacking adventure - the small wooden box attached to a tree containing the trail register for the MSG. From now on, all you have to do is follow the white blazes that mark your way north to the top of the final mountain, Sunapee. 

The first day heading north is by far the easiest in terms of elevation, running along a variety of dirt roads, paved roads, and old forest roads. There are a handful of maintained shelters along the entirety of the trail and both times I hiked this trail I chose to stop at the same two shelters, the first being Crider Shelter after a hefty 20-mile day. 

Day two is perhaps the most exciting day, if you choose to complete your hike in three days, because it takes you through the town of Washington and right past the Washington General Store which caters to hikers. Inside you can charge your devices, grab some snacks for the trail, and have a trail-worthy meal from the small full-service kitchen that even offers beer and wine. The next 5 miles of trail are over a series of small humps and the summit of Lovewell Mountain. I chose to stop at the Max Israel Shelter which is nestled into a large coniferous forest. You feel like you’re deep in the woods while only being a few miles from town. 

The final day is perhaps the hardest if you follow the route I took. Although it only registers around 15-miles in length it is spent almost entirely in the woods on single track, navigating PUDs (pointless ups and downs). As a final challenge the hiker heading north sets out to climb along the granite slabs leading through the southern part of Pillsbury State Park before skirting along the edge of Lake Solitude. Another trail register is nestled at the base of the final climb to the summit of Mount Sunapee. Unfortunately, the one major downside of this trail is that if you finish it on top of Sunapee it’s pretty anticlimactic. There is no real terminus marking the finish and the top of Sunapee is covered in buildings because Sunapee has a ski resort on it. 


I would consider the MSG a moderate hike that can be completed in anywhere from 3 to 4 days. Over the 55-miles (give or take) you will gain or lose around 10,000’ of elevation and summit around a dozen named peaks.  


Getting to either of the termini is pretty easy, however if you are planning on parking a car at Monadnock State Park you have to let the park know and pay a fee per day. I chose to park at the Mount Sunapee resort parking lot which doesn’t cost any money, however I called ahead just to make sure that it was ok to leave my car there for a few days. 

Once on the trail, because it runs through a series of small towns and along roads, there are certainly many places to bailout if you need to get off trail. There are no fees to stay at any of the shelters along the trail and water is abundant but should be filtered. Respectfully, the MSG trail association asks that backpackers stay at the designated shelters and not stealth camp along the trail. 

When To Hike

The MSG can be hiked any time of the year but I would recommend avoiding it in the early spring because it can be pretty wet and muddy. The best times of year would be summer or fall.

Final Thoughts

This hike has been referred to as a mini Appalachian Trail by a few different 2,000 milers over the years. You walk along a wide variety of terrains, including rock scrambles, mini balds, and if you choose to go southbound, finishing on top of Mount Monadnock means you will have 360 degree views for miles reaching as far as Boston on a clear day. The shelters, trail magic, and Washington General Store only add to the feeling of a tiny taste of trail life. So whether you’re looking to complete a shakedown before a longer thru-hike or just trying to satiate your inner hikertrash while navigating the “real world,” I recommend this hidden gem. It is truly an up-and-coming “short” long trail so make sure it’s on your bucket list for 2023.