Great Boston area hikes w/some gain

[TwinMom+1]

Any recommendations on great Boston area treks with some elevation gain? I run a meetup for folks on the autism spectrum and their friends/family, and lately I get limited enrollment when I book hikes in NH. Looking for new Massachusetts area ideas to accommodate the group.

I run Wachusett, Watatic and Blue Hills group hikes regularly, and am contemplating a Middlesex Fells from the East journey (thank you Mohamed Ellozy for your classic site's post about this). Our family loves Mt. Grace outside Orange MA but last year I had no takers for it. Haven't run a group hike at Mt. Holyoke/Trail of the Seven Sisters although our family loves it and it's my this year's goal to drag the hubby the full 10.2 RT circuit from Holyoke to Bare Mtn - which, with its numerous PUDs, actually is around 3000' gain dep on how you count it. Plus there's a great ice cream store at the trailhead.

Feedback welcome, as are fellow hikers who enjoy hanging out with quirky yet lovable types with a rainbow spectrum of pretty amazing people.

 

[nartreb]

You've already named most of the obvious hills around Boston. I would add Prospect Hill in Waltham. I like to start from the north parking lot, cross the grassy field and follow the (somewhat eroded) trail up the middle of what was once a ski slope. At the top of that slope, rejoin the road, follow it to the old radar tower, then follow Skyline Trail to the viewpoint on the south peak. Several loop variations possible.

If you're willing to accept less elevation gain and less of a wilderness feel, you can make some loops with good views in the Arnold Arboretum and in Mt Auburn Cemetery. (The latter has a tower you can ascend.)

 

[TwinMom+1]

I would add Prospect Hill in Waltham. I like to start from the north parking lot, cross the grassy field and follow the (somewhat eroded) trail up the middle of what was once a ski slope. At the top of that slope, rejoin the road, follow it to the old radar tower, then follow Skyline Trail to the viewpoint on the south peak. Several loop variations possible.)

Thanks Nartreb!- we tried finding Prospect Hill in Waltham a year ago but got lost and ended up in some housing development of McMansions. We thought perhaps the place was no longer a hill but maybe I missed something. I'll have to go surf to see if there's another Prospect Hill. Any guidance on where to find the trailhead?

 

[JToll]

There is a nice loop trail in Myles Standish State Park

 

[nartreb]

Thanks Nartreb!- we tried finding Prospect Hill in Waltham a year ago but got lost and ended up in some housing development of McMansions. We thought perhaps the place was no longer a hill but maybe I missed something. I'll have to go surf to see if there's another Prospect Hill. Any guidance on where to find the trailhead?

The north trailhead has a big parking lot on Totten Pond Rd, across from Veterans Memorial skating rink. Google Maps shows the north end of the park road at "Prospect Hill Park", the parking lot is alongside it; you can also search for "Prospect Hill Playground."

There are several other trails with rather informal trailheads. If you ask Google for directions to "Prospect Hill" or "prospect hill lookout", you're likely to be directed to one of those, e.g. on one of several formerly-continuous streets named Prospect Hill Rd. In that case you're parking next to somebody's house and scanning the edge of the woods for an unmarked (but very well-worn) trail. Or you might get sent to the south end of the park road, which I think is always gated.

As usual, it helps to have a good map:
caltopo map with TF Outoors layer selected
Note that the parking lot at the north end of the park road was rebuilt over the past year, not a major change but most maps don't show the new shape of the parking lot and the new one-way loop to the playground.

 

[peakbagger]

Jazzbo took me on a bunch of variations of hikes around the Walden Pond area, if you avoid the actual loop around the pond there are a lot of nice fairly wild and unused paths and a few hills.

 

[Billy]

Hi TwinMom+1,
Were you on Mt Eisenhower on Sunday July 17th?
If so, I was the guy who used your camera to take a picture of you and your boys as you were packing up to leave.
It was nice to meet you.

 

[TwinMom+1]

Hi Billy - yes that was us! Belated thanks - that was such a bluebird day - I hope you had fun too. Eisenhower was our 1st 4K 20 years ago, when the boys were just 8 years old. It was fascinating being back at where we first discovered the guys' love of being above treeline and comparing reality vs memory. The talus field at 2.8 mi from the trailhead was not the scary field than I remembered, and I'd also forgotten how tantalizing it was to hear the cog and spiral through the last bit of brush before the big yellow "STOP - this is the home of the world's worst weather" sign. Sadly I think I was faster 20 years ago but heck, the shared enjoyment was even better.

 

[TEO]

Charles W. Ward Reservation in Andover. Trail Map.

 

[NHClimber]

Nobscot Hill in Sudbury, MA.

 

[mc.lynch]

Trustees of Reservations has many interesting hiking properties in MA. Most have trails with a moderate amount of elevation gain. A few charge non-members a small amount for parking, but otherwise they are free to hike. I have hiked all of the properties in Boston metrowest many times and found them enjoyable and was able to get in plenty of elevation gain in most of them.

https://thetrustees.org/places-to-go/?_place_type=regional-trail-link%2Cwoodlands-parks&_experience=outdoor-recreation&_activity=walking-hiking