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Thread: Best hikes in the Berkshires

  1. #1
    Senior Member
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    Jun 2009

    Best hikes in the Berkshires

    What are your favorite hikes that you've done in the Berkshires?
    Two main types I'm looking for:
    1) Best hikes for a 5-year-old. Looking for rivers/streams, some moderate ups and downs, and some nice views. A Berkshire version of Mt Willard.
    2) Best hikes involving long distance at high elevation. Basically a mini version (if there is one) of the Gulfside Trail or above-treeline Crawford Path.

    Trip pictures

  2. #2
    Senior Member Grey J's Avatar
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    Jul 2013
    Chattanooga TN
    There is no comparable trail to Gulfside in the Berkshires to my knowledge. They just aren't high enough. Mt Greylock is the obvious high elevation choice but at just under 3500 feet, that is not going to be similar to a NH Presidentials experience. It's still a nice hike and of course it's the Mass high point. PS Not just whistling in the dark, I grew up in Mass. Happy trails.
    "I am a pilgrim and a stranger"

  3. #3
    Senior Member Tim Horn's Avatar
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    Aug 2005
    Quote Originally Posted by Billy View Post
    What are your favorite hikes that you've done in the Berkshires?
    Two main types I'm looking for:
    1) Best hikes for a 5-year-old. Looking for rivers/streams, some moderate ups and downs, and some nice views. A Berkshire version of Mt Willard.
    2) Best hikes involving long distance at high elevation. Basically a mini version (if there is one) of the Gulfside Trail or above-treeline Crawford Path.
    The Arch bridges on the West Branch of the Westfield River. Access it near Chester . Just a nice old toll road that runs along the river.

    If you want a view try Alander and Mt Fissell. Nice this time of year but with the Laurel about to bloom there will be hoards of bees on the ridge that is covered in Lauel. Not an issue for me but if you are allergic don't try this hike in June. The Taconic Crest trail is nice hiking. At is the Hoosic Range Trail. There is good hiking in Monroe State Forest. It goes on and on.
    Pick up the AMC guide to MA for starters.
    Yes lots of good hiking in MA this time of year when it is too muddy further north.
    I hope to see you out there this weekend!

  4. #4
    Senior Member weatherman's Avatar
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    Mar 2004
    South Metro Denver Avatar: Basin Ponds Bullwinkle
    Only long high-ish one I've done goes from Williamstown up and over Greylock. You can turn around or keep going a bit further south on the AT, perhaps making a loop with a bike spot. There is really no true above-treeline in MA.

    For 5-year olds there are so many- if you're looking to stay in the general area of Greylock there are some cool "cove" type areas on the west side of the mountain, or if you're looking farther south there are some other good ones (Bash Bish Falls? Sage's Ravine?) that are pretty but not as many views. There are a lot of beaver dams and lodges in the swampy areas that you can check out with kids. Mosquitoes were our biggest problem back when we had preschoolers and tried to hike in the Berks- seemed like anyplace pretty with water had so many that we were driven out in a short time between May and August.
    --would rather be hiking than typing.

  5. #5
    Senior Member TomK's Avatar
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    Oct 2010
    Home: Northwest CT / Avatar: Madison 1985
    Monument Mountain is pretty similar to Mt Willard for distance and elevation gain, and it has a 360 degree view.

    Further south, in Connecticut, I enjoy the Waramaug's Rock at the Steep Rock Association's Macricostas Preserve. A bit more modest with elevation gain, but you can make the return hike a bit longer if you like, by chosing which branch of the trail to use for your return. It has a nice view of Lake Waramaug from the open area at the top of the hill. Low bush blueberries near the top of the ridge. Wouldn't make a special trip for it, but if you find yourself in the area...

    Still a bit shorter, still in Connecticut, I also enjoy the Pine Knob Loop, on US 7, about a mile north of the intersection with CT 4. The parking is opposite the Housatonic River, there are a couple outlooks, a short rock scramble, and one leg of the loop is right next to Hatch Brook, which has some nice cascades, more in the spring, than in late summer. You can make it longer by staying on the AT South, and then taking the Mohawk Trail .1 to the top of Breadloaf Mt, which has a modest view to the west. Return the way you came, or continue on the Mohawk Trail to US 7 and roadwalk a mile back to the Pine Knob Loop trailhead.

    Never loved your plains, your gentle valleys/Your drowsy country lanes and pleached alleys.
    I want my hills, the trail that scorns the hollow/Up, up the ragged shale where few will follow.

    High on my hills of dream, dear hills that know me/And then how fair will seem the lands below me
    How pure at vesper time, the far bells chiming/God, give me strength to climb, and hills for climbing. "Hills" - Arthur Guiterman

  6. #6
    Senior Member Mike P.'s Avatar
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    Sep 2003
    Colchester, CT
    Define Berkshires? If Western MA in general:

    For a five year old, Trail to lower or even upper Race Brook Falls, Trail to South Brace may be too steep to the top but doable to Waterfall, You can drive far enough towards Greylock and Everett that a hike is not too hard. Doing either from lower road crossings (Route 41 or several trailheads for Greylock) are good hikes.

    For other hikes, What I had researched for Berlin and Berlin's summit lookied interesting, however in high water I could not make much headway to the top. You will have lots of company on Greylock for it's views. My favorite trail is the AT south of Mt. Race's summit, you have a 1/4 mile or so of mostly cliff top walking with good views to the East. Brace on the other side of the Taconic Plateau offers views to the West and the Catskills. The view from Jug End is nice too.
    Have fun & be safe
    Mike P.

  7. #7
    Senior Member TDawg's Avatar
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    Jun 2005
    Plymouth, NH
    “5 yr old hikes...”

    Warner Hill on the AT, off Kirchner Rd near Dalton. Can’t be more than a couple miles out and back round trip. But the summit has a view of Mt Greylock from a clearing. Some of my earliest hiking memories were here. Very easy.

    Tyringham Cobble. A little more difficult but a nice 2 mi loop with open fields, mtn views, and some interesting sandstone geology.

  8. #8
    Senior Member Jazzbo's Avatar
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    Jan 2005
    Waltham, MA Jazzbo & Marty meet Bigfoot on Kennebago Divide
    My kids are in mid 20's. When it is your 5 year they are your treasure. The treasure part has worn off having passed through high school and teen age years. 5 year old kids best remember a brook where they can stop to play in the water. Hiking in humid weather means salamanders. Kids love finding salamanders. Cute little critters. Enjoy them while they last.............

    Berkshires have world class "old Growth" forest patches with 160' tall white pines may or may not mean much to even grown-ups. My favorite places in Berkshires are the old growth forest groves in Mohawk and Monroe State Forest. There is also old growth forest grove in William Cullen Bryant Homestead. But to 5 year old a big old trees don't mean all that much. It will mean more to you than him or her.
    On #67 of NE67
    On #99 of NEHH
    On #46 of WNH48

    An atom walked up to me and said "i think I've lost an electron"
    I said "are you sure?"
    It reply "I'm positive."

  9. #9
    Senior Member iagreewithjamie's Avatar
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    Feb 2013
    Worcester, MA
    The best hike in the area is the South Taconic trail. Views for miles, blueberries (if in season), and it's a really great trail. It goes right through Bish Bash Falls.
    The bees are a bit swarmy if you stop for too long, but I went in June and didn't have much of a problem.
    The best part was the laurel. When it all blooms, some of the hills along the way are entirely white and pink.

    For a five year old, you might want to check out Sages Ravine. It's pretty neat.
    Nothin' on the top but a bucket and a mop
    And an illustrated book about birds.
    You see alot up there, but don't be scared:
    who needs actions when you got words?

  10. #10
    Senior Member Stan's Avatar
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    Sep 2003
    Newton, MA
    Windsor Jambs in Windsor SF might offer a 5 year old an interesting look at a dramatic little river canyon for modest effort.

    I find an enjoyable and likely educational walk, especially for a child for whom the experience would seem especially appealing, to be at Audubon Sanctuaries where I like to stretch my legs (they don't seem to be stretching but I enjoy the walk anyway) by redlining the trails. Pleasant Valley in Lenox is one such place with a loop of at least 3 miles, depending on your route, which features the summit of Lenox Mtn. and as good of views as you can expect in most of the Berkshires.

    A child might enjoy a search for quartz outcroppings and perhaps a souvenir for the pocket or the garden and I guess I think like a child because I look for it along the trails. Though not part of trails I'm familiar with but off of a couple roads in the neighborhood of Greylock and paddling put-ins on the Housatonic River are limestone quarry tailings. Here I've found some nice lime stones to place strategically, near lilacs and lavender, in my otherwise acidic home gardens ... as a reminder to raise the alkalinity for those plants. (Adjusting acidity and alkalinity for many cultivars of hydrangea will also effect the colors of the flowers ... I think of it like litmus paper ... but I digress.)

    As for a more challenging hike with some interest in terms of views, a mountain pond and the previously mentioned Sages Ravine, I like a loop which can be done from either the east (Rt. 7) or the west, which I prefer because a loop would entail a mostly gravel road walk. My route starts at Northwest Cabin on the CT/MA state line up Sages Ravine to the AT, north over Mt. Race and Mt. Everett and down along Guilder Pond. There are shorter options available from rt. 7 but the road walk is along a busy highway.

    The excitement, and perhaps a cool dip, at Bash Bish Falls is not to be missed. Yes, there can be mosquitoes but I'd say you can't really expect to be in the best of the outdoors without encountering some sort of annoyance so learn early on how to manage them.

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