Visiting Stockbridge, MA, and the Norman Rockwell Museum

Wondering what to do or where to stay in Stockbridge, MA? Check out the Red Lion Inn and the Norman Rockwell Museum.

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Even if you’ve never visited the tiny western Massachusetts town of Stockbridge, MA, chances are you’ve probably sung its name a time or two (or more) thanks to James Taylor’s popular 1970 lullaby “Sweet Baby James.” The song includes the line “The first of December was covered with snow, and so was the turnpike from Stockbridge to Boston,” and when I heard him sing it recently in New Hampshire, a great cheer went up from the crowd at the line, as I’m sure it does every time he sings for a New England audience.

130 miles west of Boston, in fact, and tucked into the Berkshire hills, Stockbridge represents to many the very best of small-town New England. What began as an Indian mission prospered to a resort town with the most famous Main Street in America thanks to a memorable Norman Rockwell painting. While still maintaining its rural village feel, Stockbridge draws throngs of visitors each year — in my case for the chance to eat lunch in one of the nation’s oldest continuously operating historic inns (the Red Lion Inn) and tour a museum dedicated to a beloved American artist (the Norman Rockwell Museum).

If our visit had been a few weeks earlier we would have seen the town aglow in the show-stopping colors of the autumn foliage, and if we’d waited a few weeks, we could have seen Main Street decked out for the holidays, but since free weekends are few and far between, early November it was.

Visiting Stockbridge, MA, and the Norman Rockwell Museum

Visiting Stockbridge, MA should always include a stop at the Red Lion Inn.

We parked on Main Street and followed our grumbling stomachs to the historic gem, the Red Lion Inn, for lunch. The Inn (originally named Inn at the Sign of the Red Lion) was founded in 1773, making it older than America itself. Throughout its history the Inn has had several names, but has always been identified by the red lion. Former guests include five presidents and numerous other notable figures, including Nathaniel Hawthorne and Henry Wadsworth Longfellow.

The facade is a bit peculiar with its four stories of windows in various shapes and sizes, but when you consider the Inn has stood and operated (and grown) continuously from the same spot for over two centuries, you only feel humble appreciation for the opportunity to walk up the steps of its large, wide front porch and (if its nice outside) settle into a rocker…

Visiting Stockbridge, MA, and the Norman Rockwell Museum

The Inn is known for its historic charm — and enjoying the lobby and front porch is free!

…or (if its cold) head inside to settle next to the fire in the lobby, which has the feel of a living room parlor from the 1800s.

Visiting Stockbridge, MA, and the Norman Rockwell Museum

The cozy lobby is a favorite. Visit during the cooler months and enjoy the crackle of the fire.

Today, the Inn has 125 guestrooms ranging from B&B with a shared bath, to deluxe suites. A working Birdcage elevator lends historic charm, as do the “telephone booth rooms” wallpapered with Saturday Evening Post covers, and Staffordshire china above the doorways. Guests and visitors have the option of three different dining options — the upscale main dining room or intimate wood-paneled Widow Bingham’s Tavern on the main level, or the lower-level Lion’s Den Pub.

Visiting Stockbridge, MA, and the Norman Rockwell Museum

Pub fare was the perfect lunch during our chilly early November visit.

Craving pub food with local cider and beer on the side, and mindful of our wallets, we opted for the Lion’s Den Pub, and were instantly pleased with our choice. The low tin ceilings were painted dark red, and booths with plush backs ran the perimeter of the room, snuggled up to tables. We were seated next to a crackling fire (a REAL fire!) that made the whole experience deliciously warm and intimate.

SEE MORE: 5 Best New England Restaurants with Fireplaces

Visiting Stockbridge, MA, and the Norman Rockwell Museum

There’s a fire in the pub, too.

The meal was great, too. We started with herbed cheese, seed crackers, and fruit with our drinks (Berkshire Brewing Company beer and Johnny Mash hard cider) before enjoying sandwiches — a grilled veggie panini for me and a “day after Thanksgiving” style sandwich for him.

Visiting Stockbridge, MA, and the Norman Rockwell Museum

Cozy enough for you?

Full and warm, we headed back out to wander past the seven buildings on Main Street that former resident Norman Rockwell made famous when he painted them at Christmastime, but more on those later!

Visiting Stockbridge, MA, and the Norman Rockwell Museum

The charming Main Street scene in Stockbridge.

Norman Rockwell lived in Stockbridge from 1953 until his death in 1978 at the age of eighty-four. He loved the town, and it loved him back. As proof of this, the Norman Rockwell Museum was founded in 1969 with the help of Norman and his third wife, Molly. The museum’s current home, built in 1993 and just a short ride from Main Street, is set on 36 scenic acres and houses the largest collection of original Norman Rockwell art in the world.

Visiting Stockbridge, MA, and the Norman Rockwell Museum

Next up? The Norman Rockwell Museum.

They have a wonderful website — if you’d like to get a better look at any of the paintings I mention in this post (they allow no-flash photography in the museum, and although it’s hard to capture Rockwell in the best of conditions, I did my best — all images in this post were taken by me), head over and browse the collection.

Right away I sought out one of my favorite Rockwell paintings (and maybe yours, too), 1948’s The Gossips from the March 6 Saturday Evening Post — its most popular Rockwell cover in thirty three years. Apparently inspired by a personal experience, Rockwell didn’t feel comfortable going ahead with the idea until he included his wife (second and third in the third row) and himself (bottom row in the gray hat) in the “gossip chain.” Naturally, he is the final one to hear the gossip, and gives the original whisperer a piece of his mind.

Visiting Stockbridge, MA, and the Norman Rockwell Museum

1948’s The Gossips from the March 6 Saturday Evening Post — its most popular Rockwell cover in thirty three years.

Wandering through the main level took us past the museum’s permanent collection, main gallery, sports gallery, and display of The Four Freedoms. These were some of my favorites…

Visiting Stockbridge, MA, and the Norman Rockwell Museum

Some of my favorites at the Norman Rockwell Museum. Clockwise from L-R: The Lineman (1949), Before the Shot (1958), Repairing Stained Glass (1960), Saying Grace (1951), The Recruit (1966)

The Four Freedoms series was painted in response to a World War II speech by President Franklin Roosevelt, in which he described four principles for universal rights: Freedom from Want, Freedom of Speech, Freedom of Worship, and Freedom from Fear. Originally published by the Post, the paintings then went on tour to sixteen different US cities to raise money for war bonds.

Visiting Stockbridge, MA, and the Norman Rockwell Museum

The Four Freedoms. Clockwise from L-R: Freedom from Want, Freedom from Fear, Freedom of Worship, Freedom of Speech

Rockwell loved using “everyday folks” like family, friends, and neighbors as models in his paintings, including himself! Here, you see a photo of Rockwell posing for a spot in Casey at Bat, along with his likeness in the final result. As soon as the medium became widely available, Rockwell painted from photographs rather than real-life models.

Visiting Stockbridge, MA, and the Norman Rockwell Museum

Norman Rockwell often served as his own model.

In 1963 Rockwell ended his relationship with the Post and began working with Look magazine, which allowed him more creative freedom in pursuing depictions of social issues. Here, photographs of the model and the dress she wore from his iconic 1964 civil-rights-inspired painting The Problem We All Live With are on display (the painting itself hung in the White House from July – October 2011 at President Obama’s request, and was part of a Rockwell exhibit at the Crocker Art Museum in Sacramento during my visit). It shows six-year-old Ruby Bridges on her way in to an all-white public school in New Orleans on November 14, 1960 in the midst of racial desegregation, a thrown tomato smearing the wall behind her.

Visiting Stockbridge, MA, and the Norman Rockwell Museum

The making of The Problem We All Live With.

Another favorite of mine from this era is New Kids in the Neighborhood, again for Look magazine, in May 1967. Two groups of children take each other in, one African-American and one white, but each with a pet and baseball equipment.

Visiting Stockbridge, MA, and the Norman Rockwell Museum

New Kids in the Neighborhood (1967)

One of Rockwell’s most enduring Christmas and small-town America scenes (and a particular favorite in Stockbridge) is Stockbridge Main Street at Christmas, mentioned earlier. He began painting it in 1956, but it took until December 1967 to complete.

Visiting Stockbridge, MA, and the Norman Rockwell Museum

Stockbridge Main Street at Christmas (1967)

Here you can see the buildings as they look today, alongside their painted counterparts.

Visiting Stockbridge, MA, and the Norman Rockwell Museum

Stockbridge Main Street at Christmas — then and now.

Every year on the first weekend in December, Stockbridge celebrates the painting and their beloved former resident by recreating the scene (complete with vintage automobiles) as part of its Stockbridge Main Street at Christmas. The popular weekend-long event also includes a house tour, caroling, and concert.

Stockbridge Main Street at Christmas | Home for the Holidays
The Red Lion Inn in Stockbridge, MA | A Historic New England Inn at Christmas

The lower level of the Norman Rockwell Museum has a jaw-dropping exhibit dedicated to Rockwell’s 323 covers for The Saturday Evening Post over the 47 years he worked with them. Arranged chronologically, the framed covers fill three of the room’s walls, while on the fourth, a short but thorough documentary on the artist’s life runs on a loop.

Visiting Stockbridge, MA, and the Norman Rockwell Museum

Admiring Rockwell’s many Post covers.

It’s a terrific display, and when seen all at once it’s fascinating to observe how Rockwell’s style grew and changed over the years, as the nation he so lovingly and faithfully painted did as well.

Visiting Stockbridge, MA, and the Norman Rockwell Museum

Have a favorite Post cover? You’ll find it here.

I’ve always had a history-nerd soft spot for the original Rosie the Riveter cover from May 29, 1943, so I sought her out right away. In truth, I could have spent hours looking at the covers, but it was getting late.

Visiting Stockbridge, MA, and the Norman Rockwell Museum

A fan-favorite from 1943.

Outside the Norman Rockwell Museum, a path winds behind the museum and takes visitors to Rockwell’s original Stockbridge studio, transported to the museum property and open to visitors from May through October. Along the way, climbing structures done by Rockwell’s son Peter decorate the grounds.

SEE MORE: Norman Rockwell’s Studio at the Norman Rockwell Museum in Stockbridge, MA | Photographs

Visiting Stockbridge, MA, and the Norman Rockwell Museum

Rockwell’s studio is nearby, and is open for tours seasonally.

Unfortunately, I was four days too late to see inside the studio, but that didn’t stop me for posing from a picture at the door. You take what you can get, right?

Visiting Stockbridge, MA, and the Norman Rockwell Museum

This was as close as I could get!

Seeing the inside of the studio is one reason to return to Stockbridge, but it’s far from the only one. I could also check out the Berkshire Botanical Garden for a springtime woodland walk and picnic, take in a summer concert at nearby Tanglewood, tour sculptor Daniel Chester French’s home Chesterwood, enjoy a performance from the Berkshire Theatre Group, or relive the Gilded Age with a summer tour of 44-room historic “cottage” Naumkeag. Whew! For one small town, Stockbridge certainly has a lot to offer, topped with friendly folks and stunning scenery. I’ll definitely be back.

Have you ever visited Stockbridge, MA or the Norman Rockwell Museum?

This post was first published in 2012 and has been updated.

  • My wife and I have visited the Red Lion Inn many times, and have always considered it a treat. Also having been to The Rockwell Museum, it is a must see for anyone passing through New England. One of his works that caught my eye and I bought is “Shuffleton’s Barber Shop”. It captures in oil what is iconic to the imagery of small New England towns but also reveals a hidden, but shared interest of culture in the community.

  • enjoyed your thoughts and words immensely — an amazing beautiful place to visit. Planning on making one myself this winter —


  • Thanks for the many memories of our vacation while we were in your area in the mid 90’s. Especially Norman Rockwell museum.

  • Loved reading this wonderful piece. It is such a great little town and nothing compares to seeing the amazing Rockwell paintings in person.

  • Kathleen

    Rex and I live winters now in North Palm Beach, we are 81 and 76 years of age, and reading this article on Dec 8th, in my FL den, before an early night to bed, reminds me of our great life, six months in the Berkshires, 10 minutes from Stockbridge…over 40 years of mvisits to the Red Lion, and the Rockwell Museum. We even spent our honeymoon night there. My brother use to sing with Molly Rockwell in the choir, and we have memories of times spent with the Fitzpatrick Family, current owners of the Red Lion Inn. I will have dreams of a beer and a pizza at the Lions Den tonite. Thanks.. Kathleen O’Shaughnessy Hearn

  • Been there many times and always seems to be the first time with every visit. Sat on the front porch with my mom and my daughter, having cocktails. Thanks for the memories. I also have a copy of the street scene in my hallway.

  • Thank you for sharing the wonderful photos. It brought back memories of our fall trip to Stockbridge three years ago. I loved the studio and the children book illustrations exhibits. It was wonderful seeing a museum promoting illustrations. Stockbridge was lucky to have Norman Rockwell live there, and he was probably thrilled to live there too.
    The Red Lion Inn and Yankee Candle Shoppe brought back the delights of the town flavors.


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