Thoughts on a ten mile single car day hike in Southern New England

Looking for suggestions for a hike of 10-11.5 miles in southern New England.

Doing it as part of a Scouting Merit Badge. Must be at least 10 so the Pumpelly trail up Monodnock is a mile short. We have a rail trail in town we could bore ourselves on. Looking for views some elevation but less than 3,000 feet total (and probably less than 2500)

The two I'm thinking of right now are:

CT Option: Lion's Head & Bear on the AT from Route 41. (think it's 11 RT, I'll double check my CT/MA Guide, about 2200 elevation RT approx.)

Or

May also check how many miles it would be to head up Undermountain, Paradise Lane, up & over Bear, out to Riga Road & up Round and then back by the AT to Riga Junction & then all of Undermountain.

MA Option: Starting at Cheshire Harbor, Old Adams Rd trailhead, Old Adams Rd to AT, North on AT over Saddleball & Greylock, then back on AT & Cheshire Harbor. (Have to double check the mileage but I think it's 10+. I have Greylock only from Cheshire Harbor as 1900 elevation gain, approx. so total should be under 2500 Ft. when doing Saddleball)


Other options? (Holyokes? is it five miles from the Notch to the Holyoke House?) Taconic Crest? (I'd have to read up on where they were having parked car issues) Is there a trail system and something to see in Beartown (think that's the name of the forest in Western Mass not far from Otis and Blandford) Another five mile & back section of the AT in MA? (Becket & Walling from 20 out beyond Finerty Pond is a bit boring?)

I don't think Stratton from the south on the AT/LT is long enough

Catskills? (Other than one of the long approaches to Hunter, not sure that's 10 RT either so as nice as the CT or MA options) They aren't up for a Devils Path trip, at best Indian Head & Twin but don't think that's ten.

Thanks for any help or options

According to the Williams Outing Club guidebook, it's 6.8 miles from the Hopper trailhead to the summit of Greylock via the Money Brook trail and AT. It's 4.1 miles to the summit via the Hopper trail. You can do the math. It's probably my favorite loop on Greylock.

Here's a good loop I did a while ago. Start at Mt. Washington State Park headquarters. Hike up the Alander Mountain Trail to Alander Mountain(great views to the west). Then take the Loop trail south to the South Taconic trail. Continue south to Brace Mountain(great views in all directions) Backtrack slightly north to the Mount Frissell trail and take it past the tri-state marker to the CT highpoint on Mt Frissell(view south). Backtrack to the Ashley Hill trail and take it north back to the Mt Alander trail .8 miles from the trail head. Without the tri-state marker and highpoint, I have the mileage at 9.9 miles, so adding those should make it over 11. There is nothing steep on the loop and you get a bunch of great views. HERE is a great map of the area, and HERE is a state forest trail map.

You could go up Statton, over it and down to the pond, then around the Stratton Pond Trail back to Kelly Stand Road. There is a .5-1 mile easy jaunt back to the car. Total trip: an enjoyable ~11 miles. The last four are flat as Lincoln woods. Maybe not quite that flat- there are rocks and roots, but I can't recall any elevation to write about. Very nice trip: mountain, fire tower, pond.

Mike P. said:

Must be at least 10 so the Pumpelly trail up Monodnock is a mile short. We have a rail trail in town we could bore ourselves on. Looking for views some elevation but less than 3,000 feet total (and probably less than 2500)

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Monadnock has lots of trails. You can add distance very easily. For instance, could add Monte Rosa to the above hike.

Doug

Isnt there a through trail going over Pack Monadnock?? I'm on the road and cant think of the name. I thought it was at least 20 miles.

The Wapack is 21+ miles long, but doesn't any/many true loop options. One that might do is using the Ted's and Carolyn's trails on North pack for a 6 mile loop, then adding the 4.8 mile out and back to South Pack.

I'm was thinking the SW Mass idea would be closer, but they are both about the same from Colchester at 2:20 hrs.

Quietman said:

The Wapack is 21+ miles long, but doesn't any/many true loop options. One that might do is using the Ted's and Carolyn's trails on North pack for a 6 mile loop, then adding the 4.8 mile out and back to South Pack.

I'm was thinking the SW Mass idea would be closer, but they are both about the same from Colchester at 2:20 hrs.

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Oddly, The Greylock hike while further away, may be the easier one to reach as it has a lot of highway and then 7 moves pretty well. (better than 4 and 44 in CT)
Monadnock also is mostly highway.

Thanks for the suggestions. Don't really want to hike another 1/2 mile past the Monadnock summit if I do Pumpelly but there are tons of other trail options & the 25th WMG Guide (the old Brick) actually had a Monadnock section. When I hike in the S.Taconic, I always think of the Mt. Washington Road as cheating but in this case, I may look the other way as it's a mileage total we're looking at, not what trail and method did I reach the summit by.

Just barely outside New England, lots of nice hikes that length and longer in Harriman...

Maybe outside your driving range, but technically in southern New England, is the Skyline Trail in the Blue Hills just south of Boston. Several 10-mile loops are possible. I did this with two scouts for the 20-miler requirement of the Hiking Merit Badge. The whole trail is 9 miles end to end, and Camp Sayre is conveniently 1 mile from the trail, so we just did everything twice. You never get higher than 635' but you get a couple thousand feet of elevation gain. And from Great Blue you can see Boston (8 miles) and Monadnock (68). And only 1:40 from your town.