Rockwell Wonderland: Road Trip From Boston to the Berkshires

The Berkshires in Western Massachusetts are well worth a weekend escape from Boston

If Norman Rockwell were alive today, his portraits of modern families would hardly resemble those from the 1940s. Smart phones might be swapped out for books, takeout boxes for casseroles, and FaceTime calls for actual human interaction. But let’s face it, most of us would give up such contemporary comforts and dive right into a Rockwell painting if we could—even if just for a weekend. While we can’t offer time travel or teleportation, we can tell you to head west to the artist’s homeland for the next best thing.

The Berkshires is a picturesque region (painted by another Rockwell—Rockwell Kent—above) about two hours west of Boston. Why more weekenders don’t skip New Hampshire, Maine and Vermont remains a mystery as in the same amount of time or less, they could be surrounded by lakes, highlands, history and more. Thanks to various arts initiatives, hiking trails and wellness resorts like Canyon Ranch and Kripalu, The Berkshires is a no-brainer weekend destination.

The Old Inn on the Green in New Marlborough

Mansion Life

Old Inn on the Green in New Marlborough is a must-try for their candle-lit fine dining and wide selection of wines. The entire restaurant area of the inn goes sans electricity in an effort to give diners a sense of what it must have been like when it was a stage coach stop for people going from Boston to Albany.

Another magnificent property from a bygone era is The Kemble Inn, in Lenox. Just around the corner from the town’s charming center, the Gilded Age mansion’s white wooden exterior is classic but once inside, you’ll find an impeccably furnished modern interior, filled with both quirky and refined design elements. It’s a blissful juxtaposition. The property is an ideal home base for your area adventures.

Stroll into town to pop into indie boutiques and art galleries and pay special attention to MacKimmie Co., a carefully curated home, apparel and gift shop with spectacular wares from around the world. Just down the block, you’ll find Nudel, a farm-to-table, casual restaurant serving up a rotating menu of new American food to both tourists and locals alike.

For fancier fare in Lenox, the dining room at the Wheatleigh hotel offers French-inspired food in an exquisite 19th-century Italianate mansion set on 22 acres of grounds originally laid out by Frederick Law Olmsted. Call for reservations, as they are often closed for special events.

The Red Lion Inn Stockbridge

Take in Stockbridge

To soak in more history (or to channel your inner Daisy or Gatsby), Lenox’s Ventfort Hall Mansion and Naumkeag House and Gardens in Stockbridge are two of many spectacular options. Naumkeag, a Trustees of the Reservation property, has original furniture and art and ten acres of idyllic gardens deigned by Fletcher Steele.

Stockbridge—one town over from Lenox—is yet another area that seems stuck in time in the very best way.

Main Street Stockbridge is utterly charming and has been the subject of many a Rockwell illustration—the artist lived there with his wife and children. The celebrated Red Lion Inn is right on Main Street. On a nice day, you’ll find visitors rocking their worries away on the property’s famous rocking chair filled porch. Insider tip, they have free WiFi, which you will want to access when you’re jonesing for coverage in the mostly dead zone.

Just a short drive away is the Norman Rockwell Museum, which features Rockwell’s art studio, the largest collection of his art and rotating exhibitions on American illustration. Also, make sure to check out the nearby Chesterwood, the home, studio and gardens of Daniel Chester French, sculptor of the Lincoln Memorial.

Monument Mountain in Great Barrington

A Town for All Seasons

Great Barrington makes for phenomenal day tripping—it’s a buzzing South Berkshires anchor town thanks to area colleges and private schools and lots of folks with second homes there. Most of the businesses are open year-round.

Wear your walking shoes to cruise the town center which is chock-full of stylish boutiques, gift shops stocked with locally made goods and charming eateries. 

Turophiles will delight over gourmet cheese shop Rubiner’s Cheesemongers & Grocers and Rubi’s Cafe right on Main Street. Fromagier Matthew Rubiner learned the tricks of the trade in Boston and now has a bustling store and casual lunch spot around the back. Here you can find delectable dairy products, charcuterie and fine accompaniments.

Rubiners Cheesemonger's and Grocers

Jewels & Brews

If you’ve had your fill of shopping and are in the mood to walk off your decadent lunch, enjoy the bucolic landscape on the Riverwalk along the Housatonic River. Put your phone on silent and soak in Mother Nature and her splendor.

At the far edge of Great Barrington is a jewelry store—McTeigue & McClelland—in an old mansion where artisans make the jewelry on-site. More area picks include antique stores and tasting rooms in Sheffield, including Big Elm Brewing and Berkshire Mountain Distillers; Grenadier Pottery is one great reason to find the tiny town of Monterey; West Stockbridge is home to No. Six Depot Roastery & Cafe; and affordable local art can be found at the St. Francis Gallery, a former church in South Lee.

With several towns to discover and hundreds of locales to experience, you might want to turn your weekend Berkshires getaway into a week-long retreat.