Suggestions for a Berkshires vacation.
May 27, 2006 6:46 AM   Subscribe

Vacationing in the Berkshires this summer...

My husband and I will be vacationing in the Berkshires this summer and need suggestions on what to do, where to eat, etc.

We love coffee, microwbrews, architecture and nature.

We actually were thinking of heading into New Hampshire and Vermont too because we will be in the Berkshires for 8 days. So, anything within a 2 to 3 hour radius is fine.

Any suggestions would be helpful.
posted by alexmikayla to Travel & Transportation around Massachusetts (17 answers total) 7 users marked this as a favorite
South county (Lenox, Great Barrington, etc) is more heavily touristed and much more upscale; it's where most of the obvious stuff like Tanglewood, Jacob's Pillow, etc are located. Lots of good restaurants and artsy tchotchke shops in both of those towns.

Pittsfield is the dividing line between south and north. There is no reason whatsoever to stop there. But there's a great pub on Rt. 7 a bit north of Pittsfield called the Old Forge -- gets busy early on weekends, so be prepared for a wait, especially if you want the patio.

North county is a little quieter and less tourist-oriented; it's also where I live, so I'm a bit more familiar with it :) The Miss Adams Diner in Adams is decent; there's not much else there. North Adams is scruffy but nice. It has MassMOCA, of course, which is usually worth a visit, and a few little coffeehouses on main street (Cup & Saucer has free WiFi). Also Hickory Bill's BBQ (half a block off main street) is excellent. (Get it to go; have a picnic.) Williamstown is your basic picturesque New England college town; the Clark museum is surprisingly good.

Plenty of good hiking around Mt. Greylock (which is basically between Adams and Williamstown) and east between Savoy and Florida. But I'm a lazy bastard so I don't know where any of the trailheads are.
posted by ook at 8:27 AM on May 27, 2006

MassMOCA is definitely worth the trip by itself. We stayed at the Holiday Inn which was fine, but I've heard very good things about MassMOCA's boutique hotel, Porches.

Williamstown has nice University architecture and a couple coffee shops. Can't help much on nature, but for microbreweries, I recommend Vermont!
posted by Xalf at 8:39 AM on May 27, 2006

Just remembered I had a bunch of Williamstown-area trail descriptions from one of my more active friends, who I hope won't mind if I repost them here. The directions probably aren't clear enough, I'm afraid, but hopefully this'll give you enough google fodder to find more detailed maps. (Or you can pick up a trail guide just about anywhere.)

Pine Cobble boulder field, aka "Chestnut Trail". Trailhead, such as it is, is on Chestnut Street, one of the streets off of North Hoosac (in Williamstown). Probably a bit over a mile up there, and then back for a round trip of around two miles. It is uphill, but nothing like the Dome, or Greylock, or even Pine Cobble. The boulder field at the top is great fun for scrambling.

Taconic Crest to the Snow Hole: Trailhead is at Petersburg Pass (go west from Williamstown, about halfway to Troy.) Around 3 miles to the snowhole, so 6 miles round trip. Nice views at the clearings. Pretty steep beginning, and at least one steep section about a third (quarter?) of the way through, but if memory serves, the rest is pretty flat. It gets pretty windy where the forest opens up in to clearings.

The Dome: big round peak north of Williamstown. the trailhead is on White Oaks Road, further up than the parking area for Broad Brook. 6.2 miles round trip. The top of the Dome is a really neat ecosystem though: evergreen forest and upland bogs that are much more like Canadian forests than the typical New England forest. It isn't a bare mountain top like Greylock, but there may still be some views down where the trees are deciduous.

The Hopper trail. Trailhead is near the Green River swimming hole, on Hopper Road. This is one of the many, many ways up Greylock; it's 2.4 miles up to Stony Ledge, or 4.1 up to the summit.

So there's that.

Also, back to my favorite hobby: I should mention that Rip, the bartender at Cafe Latino (in the MassMOCA complex, to your left before you enter the museum itself) is the best bartender in the world. Their food isn't bad either.
posted by ook at 9:00 AM on May 27, 2006

On preview: repeating a bit of others' posts here; too lazy to edit.

Outdoors stuff: Mount Greylock is a must. The easiest way to the summit is to drive. Climb the stairs to the top of the War Memorial and drink in the view. If you feel like a hike, the visitor's center has plenty of maps and good advice.

Shorter, but pleasant and rewarding hikes may be found at Monument Mountain just north of Great Barrington.

Also the Taconic Crest Trail offers pleasant, mostly flat ridge walking with great views, much of it on old woods roads. A major trailhead is at the parking lot of the abandoned Petersburg Pass ski area, just west of Williamstown on Rte. 2 (a/k/a the Taconic Trail.) The old ski area can be fun to poke around too, if you're into that sort of thing. Be prepared to share this trail with (illegal but present) ATVs.

Also consider Williams College's Hopkins Memorial Forest or the popular Class of '33 trail on Berlin Mountain. The Class of '33 trail offers strenuous, but rewarding hiking to the top of Berlin Mountain and the TCT.

Some good sources for local outdoor knowledge: The Williams Outing Club publishes a guidebook. They keep a copy in the stacks at the Milne Memorial Library in Williamstown or you can purchase it locally. Also, the folks at The Mountain Goat are a great source of hiking advice, maps, guides and gear. Also The Arcadian Shop in Lenox.

If you venture into Vermont, consider hiking to the top of Stratton or Bromley Mountains on the AT (convenient trailheads -- email me for directions.) Also lots of good trails around Mount Equinox south of Manchester, VT (and definitely do the beautiful drive to the summit, complete with its own Shining-esque abandoned inn.) Also within the 2-3 hour range is Mount Monadnock in New Hampshire (supposedly the second-most climbed mountain in the world after Mount Fuji.) It's about 1.8 miles and 1800 ft of vertical to the top from the main parking lot. Great views off a rocky summit.

You can also look into whitewater rafting on the Deerfield River, but I've never done it myself. The river valley between Charlemont, MA and Readsboro, VT is worth checking out if you're in the neighborhood -- it feels like a little bit of West Virginia transported to the Northeast.

Architecture: visit The Mount (Edith Wharton's estate and gardens) which has been recently restored. Disclaimer: my brother used to work there.

If you haven't done so, make your reservations ASAP. When Tanglewood is in full swing, weekend vacancies are next-to-non-existent.
posted by Opposite George at 10:02 AM on May 27, 2006

We love coffee, microwbrews, architecture and nature.

For the architecture part, spend an afternoon strolling around Williams College, and maybe check out this exhibit at the Williams College Museum of Art.
posted by soiled cowboy at 10:16 AM on May 27, 2006

Check out the Williamstown Theater Festival, the Berkshire Theatre Festival (Stockbridge) and Shakespeare & Company (Lenox).

Also consider visits to the Norman Rockwell Museum (Stockbridge); Herman Melville's home, Arrowhead (Pittsfield), the Chesterwood Estate (Stockbridge), Hancock Shaker Village (Pittsfield) and Edith Wharton's The Mount (Lenox),

'Discover the Berkshires' suggests some day trips.

Also of interest: Bershire Books.
posted by ericb at 10:42 AM on May 27, 2006

I gotta say, Pittsfield is pretty unremarkable--it's a giant Superfund site, actually--BUT for some of its excellent architecture. Really gorgeous Victorian houses. And also Herman Melville's Arrowhead, where he lived for awhile.

Also, if you decide to go to Vermont, there's the Bennington Potters and the Blue Ben Diner.
posted by veronica sawyer at 10:48 AM on May 27, 2006

Whoops, didn't preview.
posted by veronica sawyer at 10:48 AM on May 27, 2006

On the total indulgence end-of-the-scale consider a three-day retreat at the flagship Canyon Ranch in Lenox.
posted by ericb at 11:18 AM on May 27, 2006

There have been lots of great suggestions here. I definitely second Chesterwood and the Hancock Shaker Village (the big one on route 20 as opposed to a smaller shaker site in Chatham, NY).

I would also recommend dining and/or taking in some music at Club Helsinki in Great Barrington, MA. There are tons of good restaurants in Great Barrington (and it's a neat little town to walk around too). The sushi place Bizen has gotten very good reviews in the past, though I have never eaten there myself. Stop in Guidos in Great Barrington (or Pittsfield) for some great gourmet food if you feel like cooking (they have prepared stuff too).

You should also go to the Red Lion Inn in "downtown" Stockbridge, MA. Sip your drinks in wicker rockers on the porch and then eat. You'll feel like you're in a Norman Rockwell painting. And you are since he painted the Inn numerous times!

The Clark Museum has a fabulous collection. As the story goes, Mr. Clark wanted to put his art collection somewhere relatively safe in the event of a nuclear holocaust -- and Williamstown was it!

You should also take a drive over to Northampton, MA and nearby Amherst (via the route 9 scenic route or I-90 east to 91 north to I think it's exit 16 or 18). Northampton is the larger of the two. There are lots of shops and restaurants and bookstores in dowtown Northampton. It's a downtown that hasn't been decimated by suburbia and such (just like Great Barrington is). Smith College in Noho has a nice art museum too. Paul and Elizabeth's is pretty popular (in Thorne's market on Main Street) but there are tons of nice restaurants. The Raven is one of my all time favorite used bookstores. Given the 5 colleges in the Northampton-Amhert area, there are a lot of great books available. And by all means, be sure to take in some music at the Iron Horse Music Hall (or one of it's several venues in downtown Noho). It gets a never ending stream of top notch performers coming though.

While I have spent much time in "the big city" of Northampton (just kidding), I have grown very fond of the somewhat smaller Amherst (it's only about 10 miles east via Route 9). The Emily Dickenson home is well worth a trip. You can also pay homage to her at her grave in the little graveyard behind the Mobil station on route 116 in downtown Amherst. All the women students from the nearby colleges make the pilgrimage. Judies is the popular and ecelectic place to eat. Stop in The Black Sheep for some nice sandwiches and coffe and pasteries.

While all the places I've mentioned so far are in or within close proximity to the Berkshires, I have to put in a plug for a little longer trip to Saratoga Springs, NY (aka Saratoga via I-90 west to exit B-1 through Albany to 87 north (the Northway) at exit 24 to exit 15 or so.) Saratoga is another hopping place with an old fashioned vibrant downtown. It is quite the hotspot from the end of July to Labor Day due to Saratoga Race Course (the flat track, not the harness track) being open. Lots of folks from NYC and everywhere go to the track and then eat/drink at one of the many restaurants in Saratoga. Siro's is pretty darn popular and will be happy to take your money in exchange for a nice meal. Though, I'd probably go back into Saratoga and try Hattie's or Wheatfield's. Food at the track really really sucks (crappy pizza and such), so be sure to bring you own lunch from perhaps the gourmet deli in Saratoga called Putnam Market.

Nearby SPAC is our version of Tanglewood. You can see better from the lawn at SPAC (Tanglewood is flat as a pancake) and the food selection at Tanglewood was minimal last time I was there. At least you can eat at the Hall of Springs at SPAC. Tanglewood has James Taylor every fourth of July, though, which is a dream come true in my estimation. Make reservations early if you want to do an overnight trip. Housing will be tight in August.

Enjoy. The Berkshires are lovely. They are truly a gift.
posted by bim at 1:04 PM on May 27, 2006 [2 favorites]

Calrification: Great Barrington has NOT been decimated by suburban malls and such. It's quintessential New England. The emphasis in my sentence wasn't clear. Mea cupla.
posted by bim at 1:26 PM on May 27, 2006

And you are since he painted the Inn numerous times!

The Red Lion Inn is there on the right in Rockwell's Stockbridge Main Street at Christmas.
posted by ericb at 1:30 PM on May 27, 2006

Yup. :)
posted by bim at 1:45 PM on May 27, 2006

And you can also visit the Kripalu Center in Lenox if that's your thing.
posted by bim at 2:00 PM on May 27, 2006

You should also take a drive over to Northampton, MA

If you make it to Northampton, be sure to check out the Art-O-Mat at Faces of the Earth on the main drag. Also, the Whatley Antiquarian Book Center is a great used bookstore a couple of exits up I-91 (x22 or 23, I think.) Their stock ranges from bargain stuff to collector's items. One more thing, if you're into needlecraft, weaving or spinning the WEBS Retail Outlet in Northampton is a 21,000 square foot warehouse loaded with an amazing collection of yarns and fiber.
posted by Opposite George at 3:31 PM on May 27, 2006

In Williamstown, on Water St., there is an absolutely baddass music store called Toonerville Trolley Records. If you like browsing through all kinds of neat stuff, popular and otherwise, go there. The owner, Hal, is able to keep an amazingly huge stock, especialy considering the store's size.
posted by Snyder at 8:03 PM on May 27, 2006

I just want to second the recommendation of Northampton & Amherst. I moved up here just to be closer to those two lovely burgs.
posted by clango at 8:20 PM on May 27, 2006

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