The Berkshires
Do as we do! Living here, Claire has some ideas from personal experience about how to spend a spare chunk of your time.
The best little…
Let’s not overcomplicate things! We’d wholeheartedly recommend…
- Coffee: , also good for working
- Breakfast: , expect a line
- Lunch: , walk in
- Nice dinner: , make a reservation
- Casual dinner: , walk in
- Pizza: , make a reservation
- Farm stand:
- Ice cream: and pat the baby cows
- Late-night drink: ’til 1 a.m.
- Picnic supplies: or
- Historic house: , underrated
- Shop: , a 50-year-old legend
- Flat nature walk:
- Hike:
- Swim:
- Scenic viewpoint:
These are all places we go often ourselves. We love them all.
Walk to town
Wake up and give yourself 2.5 hours to walk the 4 miles from the inn into town via Under Mountain Rd. I think it has got to one of the prettiest roads in America. It literally has it all:
- scenic pastures
- a charming duck pond at (an excellent high-end B&B)
- a stunning boardwalk that winds you through boggy woods before you emerge onto a gorgeous vista at , which adds 0.6 miles total out and back
- , an equestrian center in a Gilded Age estate farm that offers trail rides and you can also just swing by to pat the horses on the nose in their stables
- gorgeous historic homes, especially once Under Mountain turns into Cliffwood St. Particularly impressive are 101 Yokun (the Winthrop Estate/Ethelwynde), 106 Cliffwood (Underledge), and 80 Cliffwood (Belvoir Terrace). My personal favorites are 71 Cliffwood and 13 Cliffwood.
Right before you enter town, check out the at the intersection of Cliffwood and Main Sts. I love this little fountain because it makes me feel like I’m in Italy. I also love it because Emma Stebbins was a sculptor who was the first woman to receive a public art commission from New York City (the centerpiece of Central Park’s Bethesda Fountain) and she summered in Lenox. It was dedicated in her honor by three of her friends when she died in 1882.
Coffee and a hike
Wake up and drive to , a charming roastery with a mix of indoor and outdoor seating, from which the hotel gets its coffee.
Stroll around West Stockbridge. There’s a bunch of good shops, a beautiful old book store, and some sculpture gardens — but our favorite thing to do is just to stand on the bridge over the river.
Hike , a 1.1 mile loop leading to a beautiful waterfall.
Go antiquing
Check out and the in Great Barrington; , , and along Route 7 in Sheffield; and in West Stockbridge; or , , , and in Lee.
Working morning
Grab a coffee at . My signature order is a hot mocha with one shot of espresso. And their pastries are pretty good — I think the best in town. Lenox Coffee is a real locals spot; see if you can eavesdrop on any good gossip.
Read the Berkshire Eagle — the best local paper in America — or get some work done on your laptop in the Reading Room at the . I love this building because it reminds me of boarding school / makes me feel like I’m about to sign the Constitution.
Industrial heritage
It’s not as suitable for sightseeing as the many Gilded Age mansions, but keep an eye out for remnants of the Berkshires’ old mills and factories hiding in plain sight. The William Stanley Overlook on the in Great Barrington commemorates the birthplace of his and George Westinghouse’s alternating current transformer (and of the Stanley water bottle). Some street lamps still trace back to Westinghouse. A former Crane Stationery headquarters is now a multifunction event venue in Dalton, aptly named . The was once a major source of Chester Blue granite, and is now a good swimming hole if you’re willing and able to scramble down some rocks. Berkshire Hathaway owes half its name to up in Adams, now an apartment complex. is “the last un-condofied mill in the Berkshires” (used for photo shoots); is still operating. is an icon of GE’s reign in Pittsfield, a hulking monolith of an electrical transformer assembly building.
Other ideas
Follow the “Arlo Guthrie’s Historic Garbage Trail Walk to Massacree HD” six miles through Stockbridge and Great Barrington along the path described in “Alice’s Restaurant Massacree” (Alice being our former owner): from the original location of , to , to the , to the defunct , and down to the . Read more.
Get takeout sandwiches at . There’s nowhere to sit, so do the walking loop and eat your sandwich on a bench there. Or substitute , where Tartine founder Chad Robertson trained.
If our live music isn’t enough, try the , , , or . Mark Greenlaw’s Music in the Berkshires is the definitive guide to smaller local shows (aside from ).
Take your kids to all the animal spots: the little duck pond at , the stables at , the calf barn at , and the variety of animals at the .
If the kids have been extra good, buy them a toy at (fancier and farther away) or (less fancy and closer).
For another rainy kid-friendly night, get fried chicken or cauliflower at and then see a movie at the .
Get a classic diner breakfast at and then walk around , the ruins of an old historic home.
Get a sandwich at , a nice old-fashioned general store, and then go see .
For a rainy kid-friendly night, eat at and then go bowling at .
Get brunch at and then tour .