Go biking here quite often a lot of shade good when it's hot

started at the southern terminus at rte 63 North of Northfield Mass. and South of Hinsdale. The trail starts across rte 63 from the large parking lot, up on the berm. The trail is in poor condition at this point. The trail is not much more than a unused fire road. A better starting point would be the Hinsdale rail station. My highlight was the Ashuelot Covered Bridge. I returned to my car from that point.

I have found a nice way to link to the Windham Depot to Derry Trail. At the southern end, cross over Rockingham Road onto Seasons Lane and turn left onto Coteville Rd. At the end of Coteville there is a short path through the woods that comes out on Franklin St Ext. Follow Franklin and turn right onto Mitchell Ave. At the end of Mitchell is a path that goes to the Windham Depot.

It’s a nice short trail, and I don’t think many people know about it.

We rode much of the trail on a tour from the MA/NH line area north of Winchendon, MA to Keene, NH. It's a beautiful, relatively flat route with some great views though high water source areas, ponds and some views of Mt Manodnock then descends along the river into Keene. We were on semi-loaded touring bikes, so jumped off on roads when they paralleled the trail since the surface is a little bumpy. Hybrid or MTB's (as recommend) would be more comfortable, but for those on touring bikes, the direct route through some road less areas is well worth it.

***WARNING! This portion of the trail is challenging. I wouldn't attempt it w/o experience or a wider/gravity tire***

I started at the parking lot on Church St. Ext. It is right next to the Plummer's Landing parking lot, which is the launch site for using the river. You want the lot just past Plummer's Landing.

The trail starts off quite wide and is a very low, grassy area. It is not a well-worn dirt path. However, after approx a half mile the trail suddenly narrows and is a slender dirt line with tall, hip level grass and brush.

There are several sections with lots of very large tree roots and deep ruts in between them. There are also lots of large rocks that create issues for your pedals. You definitely need to evaluate pedal height and position to get through spots and avoid damaging your bike.

Good elevation changes at some points. Some areas were too steep to ride up. Other parts were right against the edge of the river with little to no room for error. A few deep holes were also washed out in the middle of the trail.

I'll also add that there are two bridges that are not bike friendly. There are steps at both ends, so you need to pick-up your bike.

This "greenway" section ended at E. Hartford Ave in Uxbridge, right across the street from Tri-River Health Center. All things considered, I successfully completed this portion of the trail, but it was really difficult. If I had known how it was, I would not have attempted it solo or w/o wider tires. Now you know too. For you "fat tire" folks, have a blast!

I started on a very warm day, at the parking lot on Glenwood Rd. in Rutland. This trail matches the description perfectly! Beautiful, well-shaded ride and that is pretty continuous. I learned Rutland is the higher point of the ride, so all my work was on the way back from Oakham. But, it was very manageable and well worth the 16+ miles roundtrip.

Nice stretch of paved trail between Winchendon and Gardner, MA. It’s a quick 14 mile out and back with only one small stretch where you have to merge onto a road to find the trail again.

We bicycled a sort of loop, from Mosely Woods parking lot, along Merrimac River, crossing to Salisbury and then returning via I-95 bridge bike path. The latter was our true goal, as this was a mighty project! From the start and throughout, we had some head-scratching moments trying to find our way on the network of rail-trails and roads. I'm not sure if it's the fault/responsibility of the municipalities, the DOTs, or the trail organizations, but there are few, if any, signs indicating bikeways. This struck us as odd because in many other areas throughout Essex County in Massachusetts, and in parts of NH and ME, we have seen copious signs for the East Coast Greenway in remote countryside locations.
Before I say more on that, we enjoyed the gravel-paved Marsh Trail and Ghost Trail. The latter was shaded and welcome on a very hot summer day. The mile or so of asphalt-paved trail that parallels I-95 and crosses the Merrimac is great for getting from A to B, but it's open and not especially pleasant except for the river views, which can be enjoyed from two bump-outs on the bridge and include historic interpretation signs. (A note: if you are nervous crossing major bridge structures on bicycle, this is a good crossing. I have minor such fears, but felt completely comfortable.)
Back to signs. There are signs. But I don't think they are always where they should be, nor say what they should say. More than once, we came to intersections of various kinds and it was unclear where each option would take us. In some places there are posts with trail names and mileage., but few signs to provide context. Within long stretches of the bike paths there were posts indicating mileage (for what reason, I have no idea). Coming from the Ghost Trail there was no explicit sign to point the way to the I-95 crossing. And in Newburyport, we did not see any signs pointing the way to the trail, crossing via the Route 1 bridge. Coming off the I-95 crossing into Newburyport, we had to intuit the way back to Mosely Woods on a neighborhood road.
My suggestion is that if you are solo or with a partner, have fun and explore, and if you have to do a bit of back-tracking, no big deal. If you have kids, it might be better to thoroughly plot your route, as you don't want to be fumbling on roads with cars with kids or a larger group. That said, it would be a nice adventure to cross by two different bridges and experience a variety of trail types and scenery that runs the gamut from marsh, woods, industrial (including a massive solar array), neighborhood, etc. It is almost all flat, and eminently do-able for people of various fitness levels and bike types.
A note: the Route 1 bridge does not have a bike lane, so you must walk your bike across on a sidewalk, and will likely encounter others either on bike or foot in either direction.