Here are a few more hikes that you can do with a little one.
Mt. Wachusett – Princeton, MA.
The closest real “mountain” to Boston. Well, it looks like a mountain at least. All trails on Wachusett are pretty short being in the one or two mile range. I suggest taking the West Side Trail from West Princeton Road to the summit. There is a little bit of steepness and rocky footing but it should be fine in dry weather. Despite this mountain’s proximity to Boston and incredible view from the summit, I have never encountered massive crowds here. Wachusett State Park Map
Crow Hills – Westminster, MA.
The Crow Hills are in the western half of Leominster State Forest. There is good hiking with somewhat limited views. There is a cool rock climbing area in the northern end of the area. The yellow blazed Midstate Trail goes through here and is a good place to start exploring this place. Leominster State Park Map
South Monoosnoc Hill – Leominster, MA.
A great spot that is relatively undiscovered. This is the high area of hills that you can see off of RT 190 as it merges to RT 2. It is sparsely traveled, which makes it ideal for those with ill-behaved dogs or with small children who walk around aimlessly. This is a great hike for those with very small children as there are some good views from up here but the footing is flat and stable throughout.
Mt. Everett – Mt. Washington, MA.
We did this from the parking lot of the state park, which lies most of the way up the mountain. There is a road that goes up to the summit which is a nice option for those with very small children. The summit is really interesting with a lot of good directional views. Mr. Race a bit further south has a 360 view for those willing to put in an extra few miles but you might want to save that for adult time only. This is a bit further from Boston than the rest of these here at over two hours or so but well worth the trip – especially if you stay overnight.
Blood Hill – Ashby, MA.
There is one way to the top. Go down Erickson Rd. and follow the sign to the trailhead. This is a flat hike with no scrambling which is perfect for hikes where you must carry your child. It is a lot like the Monoosnoc Hill area in Leominster. This hike is recommended as a winter hike since the footing is good.