In Great Barrington, Mass., full of cute boutiques and restaurants, the Berkshire Mountains tempt hikers. (Michael Kearns/For The Washington Post)

About halfway through our weekend visit to Stockbridge, Mass., I told my friend Mike, “I kind of wish we’d see just one ugly sight. Just for contrast, you know?”

He knew what I meant: Each church we passed was more pristine than the one before, every lawn well manicured, every dog appropriately groomed. Living in downtown Hartford, Conn. (not a bad-looking place, itself), as we do, we’re accustomed to having the pretty parts grounded by a grain of grit. So this incessant beauty was getting to be a bit much.

We put the top down on the Jeep the Saturday before Memorial Day to drive 90 minutes northwest to see the Norman Rockwell Museum. We got a later start than we had hoped, then stopped to help a couple from Brooklyn change a flat. By the time we got to the museum, it was nearly closing time.

We hadn’t packed for overnight travel, but we decided to stay the night and try the museum again the next day. Once we found a spot where our phones could get signals — an ongoing challenge in this hilly land — we called the famous Red Lion Inn to see if a room was available. Surprisingly, on this holiday weekend that marks the start of one of the area’s peak seasons, one was — but the inn wanted $285, plus tax, for a room with two single beds, and it had a two-night minimum. Fueled by spontaneity, we drove down the road toward Great Barrington, where a cluster of chain hotels seemed like our best bet. Just a few minutes out of Stockbridge, though, Mike pulled a U-turn. He had spotted a roadside motel and figured that we should check it out.

It was the first of several serendipitous moments that made our Memorial Day weekend in the Berkshires, well, memorable.

I had promised my editor that I wouldn’t use the too-easy word “picturesque” when writing this story. But, honestly, that word might have been invented to describe the village of Stockbridge. Norman Rockwell captured his adopted hometown’s quaint, quintessential New Englandness in his 1967 painting “Stockbridge Main Street at Christmas (Home for Christmas).” To my mind, the scene could use a few potholes.

Settled in 1734 by British missionaries as a reservation for a Native American tribe that had helped out during the French and Indian War, Stockbridge today is a tourist haven, with boutique-style shops and restaurants up and down the main drag. The Red Lion Inn, which dominates the streetscape at the town’s main intersection, opened in 1773 as a stagecoach stop. The stagecoaches are long gone, replaced largely, it appears, with Jeeps.

We didn’t book that room at the inn, but we did take part in the Red Lion tradition of sipping a drink on the porch. I ordered a gin and tonic; when the server asked what kind of gin I preferred, I said, “Surprise me.” That turned out to be a sound strategy; he chose locally crafted Greylock gin, which I liked so much that I stopped at a package store (New Englandese for liquor store) for a bottle to bring home. We didn’t get to try the Red Lion’s food, though, as local law prohibits the serving of food on the porch. Instead, we were given a tiny bowl of “salty snacks” — exactly as they sound — to go with our drinks.

Illustrator Norman Rockwell’s studio is preserved on the grounds of the Stockbridge museum that bears his name. (Michael Kearns/For The Washington Post)

Stockbridge is one of several smallish towns (notably neighboring Great Barrington and Lenox) nestled among the Berkshire Mountains in western Massachusetts. Among its many crowd-drawing attractions is the Norman Rockwell Museum, which houses the world’s largest collection of original Rockwell art, most of it illustrations for covers of the Saturday Evening Post and Look magazine.

The museum, which attracts an astounding 200,000 visitors a year, rotates its stock of paintings in the galleries frequently, so sometimes a picture you really wanted to see isn’t on view. But there always is a pleasing assortment of beloved images hanging there. And Rockwell’s iconic “Four Freedoms” paintings — so familiar yet still compelling in person — are always there, in a central gallery of their own. We strolled around for an hour or so and then joined a crowd for a lively gallery talk before walking across to Rockwell’s art studio, which is furnished to look just the way it did when he last used it.

That bottle of Greylock gin wasn’t the only souvenir I bought. Stockbridge and Great Barrington have lots of little shops filled with pretty things to spend money on. I resisted the urge to add to my collection of vinyl LPs in one funky little place, but I did indulge in a handmade pair of earrings at a crafts store, where I also admired an eensy, weensy blown-glass butterfly. When Mike went to buy it for me, though, it had already been rung up with my earring purchase. The shopkeeper was sorry about messing that up, so she kept Mike back a moment as we were leaving, pressing something into his hand. On the street, he gave it to me: a small, hand-carved wooden heart.


You’re not likely to starve in these towns — at least, not if you’ve got money to burn. We passed a busy-looking Mexican restaurant on the way to Great Barrington, but we wanted to nose around a bit more before choosing a place to eat. In town, we found many kinds of eateries, with cuisines including Indian, Japanese, Mediterranean and American. Bypassing Baba Louie’s, a purveyor of organic sourdough pizza that gets high marks on but was packed when we arrived, we stopped at GB Eats, a homey diner where we sat at the bar and ordered way more food — a couple of sandwiches, fries and a big salad — than we needed.

Besides a jumbo-sized mimosa, the highlight of GB Eats was our server, who proudly and knowledgably shared historical information. He recommended that we visit Monument Mountain, where Herman Melville and Nathaniel Hawthorne reportedly once picnicked and discussed Melville’s ideas for a novel he was working on. Something about a white whale. . . . The story, which we heard from others around town, sounds apocryphal. On the other hand, Melville did dedicate
“Moby-Dick” to Hawthorne.

The Briarcliff Motel was a real find. Owners Richard Proctor and Clare Weatherall, both thoroughly British, renovated this 1960s strip motel, turning it into a simple-but-chic modern hotel. We got one of the 16 rooms because another guest had accidentally booked two when she needed only one. After we checked in, I wondered aloud about the weather and whether we needed to put the top up on the Jeep. After we freshened up (having bought travel-size toiletries and socks from the dollar store) and called our new friends from Brooklyn to make sure that they had their tire fixed, we headed out for the evening. Taped to our doorknob was a note from the gentleman who had checked us in: “Only a 20% chance of rain, but the tiny storm cells look intense.”

The furnishings at the Briarcliff are mostly from Ikea (which made me feel right at home); clusters of unframed vintage photos, handwritten notes, tiny prints, and other scrapbooky items are tacked to the wall between the beds; the office has a box full of DVDs for guests to borrow; the room keys are real keys, not cards. But perhaps our favorite feature was the outdoor gas-fire pit, ringed by chairs. We landed there late Saturday night after sharing some drinks with an impossibly young and attractive couple from Manhattan at the Red Lion’s four-seat patio bar. The only other guests at the fire pit were a couple in town for a martial-arts conference. A briefly uncomfortable political conversation yielded to more genial chat, during which we learned that these were the guests who had booked the extra room — the one we were about to retire to. The couple also said we really should have stopped at that Mexican restaurant down the street, Xicohténcatl, which was a favorite of theirs. Next time!

In the morning, we brought back to the room a tray of really good coffee, hard-boiled eggs and fresh-baked scones and muffins that Richard and Clare set out in the office for breakfast. Monument Mountain is right across the street, so we started our day there. After chatting with an enthusiastic volunteer, we determined that the day was too hot — and my flip-flops were wholly inadequate — for a hike. Instead, we headed for the Rockwell Museum, which pleasantly occupied us for the next several hours.

Our Jeep tour (top up for fear of rain) took us past some of the area’s other marquee attractions: Chesterfield, home of sculptor Daniel Chester French (best known in the D.C. area for creating the statue of Abraham Lincoln at the Lincoln Memorial); The Mount, home to novelist Edith Wharton; Tanglewood, a sprawling outdoor space that serves as the summer residence of the Boston Symphony Orchestra; and the Kripalu Center for Yoga & Health, an international retreat destination in its own right.

But the highlight of our day had nothing to do with architecture or the arts: For us, it was all about the cheese. We drove to Rubiner’s Cheesemongers & Grocers on Main Street in Great Barrington, where we sampled, sniffed and squeezed our way among the offerings. An hour later, we emerged with a bag full of stinky cheeses and sausages. It was time to head home. Thank goodness the Jeep top was up, because it rained so hard that we kept getting text-message alerts about local road closings due to floods.

Mike and I love going for long, random drives and seeing where the road takes us, letting spontaneity and serendipity work their magic. For that, the Berkshires is perfect.

In fact, let’s face it: This was pretty much a perfect place. Lack of warts and all.

LaRue is a freelance writer and director of writing programs at the Mark Twain House & Museum in Hartford, Conn.

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If you go
Where to stay

Briarcliff Motel

506 Stockbridge Rd., Great Barrington


Stylishly renovated 1960s roadside motel. Rooms from $90.

Red Lion Inn

30 Main St., Stockbridge


Centrally located, venerable destination with rooms, restaurant and a tavern. Rooms from $169.

Where to eat

GB Eats

282 Main St., Great Barrington


Friendly joint with escalated diner fare, staffed by folks with local pride. Sandwiches start at $10; salads at $9.

Rubiner’s Cheesemongers & Grocers

264 Main St., Great Barrington


Small shop selling a variety of cheeses, sausages, and other delicacies, with patient, informative staff who are generous with samples.


50 Stockbridge Rd., Great Barrington


Real-deal Mexican meals made with local and organic ingredients. Known for its mole, margaritas and live Mexican guitar on weekends. Entrees from $20.

What to do

Norman Rockwell Museum

9 Glendale Rd. (Route 183), Stockbridge


Museum featuring the world’s largest collection of art by illustrator Norman Rockwell, with special exhibitions of works by other artists. Admission $18; seniors $17; children 6-18 $6; free for children 5 and under.

Monument Mountain

Route 7 (across from Briarcliff Motel), Great Barrington


Hiking trails with sweeping views of the Berkshire Mountains, including Mount Greylock, the highest natural point in Massachusetts.
$5 parking fee.


4 Williamsville Rd., Stockbridge


The country home, studio, and gardens of 19th-century American sculptor Daniel Chester French. Open Memorial Day weekend through Columbus Day weekend. Admission $18; seniors $17; children 13-17 $9; free for children younger than 13. Grounds-only admission $10.

The Mount

2 Plunkett St., Lenox


Estate of 19th-century American novelist Edith Wharton, with house and garden tours, as well as and special events and exhibitions. Open May 14-Oct. 31. Admission $18; seniors $17; children under 18 free.

Hoosac Valley Train Rides

Trains depart from North Adams train station, 98 Crowley Ave., North Adams


A 10-mile, hour-long — and round-trip — train ride between North Adams and Adams, Mass., with scenic views and onboard narration. Weekends May 28-Sept. 18; special excursions in the fall and during the Christmas season. Admission $12; children 4-12 $8; children younger than 4 free. Reserve in advance.


— J.L.