Best 3-5 day Hike CT to Vermont

[goody5534]

Looking for suggestions???

[Cookerhiker]

Start at River Road outside Kent, CT, hike north to Great Barrington, Rt. 7. About 50 AT miles plus a few miles walking from Kent to the River Road trailhead. Highlights include beginning with a nice easy walk along the Housatonic River followed by some up & downs in CT in a nice forest. After ascending Bear Mountain, you have a steep rocky descent into Sages Ravine, a beautiful place to camp. You then ascend the ridgeline; the best is first: Race Mountain. Proceed along the ridge, passing over Mt. Everett the 2nd highest AT point in MA and eventually down the ridge to finish with an easy 5 miles to Rt. 7. Have a good lunch in Great Barrington.

If you can, hike in mid-spring (May) or Fall.

[takethisbread]

In season

Falls Village Ct to Great Barrington is a great hike with the Falls and Sages Ravine huge highlights.

Dalton Ma to Manchester VT would be a full 5 days likely but it is great as well, with Greylock, Stratton Pond and Stratton mtn.

Those two would be my picks.

[Driver8]

Start at River Road outside Kent, CT, hike north to Great Barrington, Rt. 7. About 50 AT miles plus a few miles walking from Kent to the River Road trailhead. Highlights include beginning with a nice easy walk along the Housatonic River followed by some up & downs in CT in a nice forest. After ascending Bear Mountain, you have a steep rocky descent into Sages Ravine, a beautiful place to camp. You then ascend the ridgeline; the best is first: Race Mountain. Proceed along the ridge, passing over Mt. Everett the 2nd highest AT point in MA and eventually down the ridge to finish with an easy 5 miles to Rt. 7. Have a good lunch in Great Barrington.

If you can, hike in mid-spring (May) or Fall.

I agree with Cooker and Bread. Either of those hikes would be excellent. If you want to mix and match, Salisbury to Jug End, Rt 41 to Rt 41, would be a good day or two, depending on your pace, then Cheshire to North Adams would, likewise, be a good day or two. Then a Stratton loop to top it off, skipping around with the automobile/s.

One nitpicking bit, Cooker: Mt. Everett is exceeded in height by several Mass peaks, even outside the Greylock Range. It's about the 10th highest peak in the state.

[Cookerhiker]

Start at River Road outside Kent, CT, hike north to Great Barrington, Rt. 7. About 50 AT miles plus a few miles walking from Kent to the River Road trailhead. Highlights include beginning with a nice easy walk along the Housatonic River followed by some up & downs in CT in a nice forest. After ascending Bear Mountain, you have a steep rocky descent into Sages Ravine, a beautiful place to camp. You then ascend the ridgeline; the best is first: Race Mountain. Proceed along the ridge, passing over Mt. Everett the 2nd highest AT point in MA and eventually down the ridge to finish with an easy 5 miles to Rt. 7. Have a good lunch in Great Barrington.

If you can, hike in mid-spring (May) or Fall.


I agree with Cooker and Bread. Either of those hikes would be excellent. If you want to mix and match, Salisbury to Jug End, Rt 41 to Rt 41, would be a good day or two, depending on your pace, then Cheshire to North Adams would, likewise, be a good day or two. Then a Stratton loop to top it off, skipping around with the automobile/s.

One nitpicking bit, Cooker: Mt. Everett is exceeded in height by several Mass peaks, even outside the Greylock Range. It's about the 10th highest peak in the state.

I wasn't purporting to speak for the rest of the state, i.e. the non-AT corridor. That's why I said "2nd highest AT point in MA."

[Driver8]

OK - I missed the "AT", C/h - but Saddle Ball, Fitch and Williams are higher than Everett, among which only Saddle Ball meets the common definition of a proper independent peak, so I gather.

Anyhoo, it's all very pretty and worthwhile. I think Greylock and neighbors are a must. The views from up top G/l are awesome on a clear day - I saw Mt. Washington both times I was up there last September - and the boreal forest on Saddleball is one of the most beautiful forests I've ever seen.

[OldFeet]

How many miles to you plan on covering? My first section was from VT route 30 to route 9 which is about 40 miles. This takes you past Stratton Pond, a very pretty spot, and over Stratton and Glastenbury Mountains. From route 9 south to route 2 in North Adams, MA is about another 18 miles and passes a couple of beaver dams. There's a pretty steep climb on both sides of route 9 but some great views from the top of Harmon Hill south of 9.

[Cookerhiker]

....My first section was from VT route 30 to route 9 which is about 40 miles. This takes you past Stratton Pond, a very pretty spot, and over Stratton and Glastenbury Mountains......

Wow, what a coincidence! That was my first AT section hike also - my first backpacking trip over 30 years ago.