On our road trip from Long Island to New England (and back) had the option of returning along coastal Connecticut from Rhode Island (RI), or to travel back on an inland route via The Berkshires. For maximum variety, and with the pull of visiting the Norman Rockwell Museum we decided to take the in-land route and were not disappointed. Find out why…
From Newport, RI to Stockbridge, Massachusetts
Our sat nav promised a 2.5-hour journey from Newport, RI to Stockbridge, MA, however in reality it took longer, mainly due to an accident outside Providence. Somewhere along the way we entered the third new state of the holiday – Massachusetts – and driving became much more enjoyable once we entered the Berkshires area with 2 lanes of traffic rather than 3 and lots of trees.
Where are the Berkshires?
The Berkshires are a region crossing two states:
- Western Massachusetts (in-between the Housatonic and Connecticut Rivers) and
- Northwestern Connecticut (‘the Northwest Hills or Litchfield Hills’).
The Berkshires are highlands and part of the larger Appalachian Mountain range. Note – there are bear warnings through the area so if you are hiking then be bear aware!
Where to base yourself in the Berkshires
Largely led by the road trip route we were taking, and to be near the Norman Rockwell Museum we ended up staying in the town of Stockbridge in the Southern Berkshires – the area in the southwestern corner of Massachusetts, bordering Connecticut to the south and New York to the west.
The Southern Berkshires are less than 2.5 hours from both New York City or Boston, making it popular with wealthy urbanites seeking a quiet sanctuary from the city in pretty, picture postcard, sleepy towns.
The area is known for its scenic hills and outdoor recreation – the perfect place to get out for lovely hikes in the mountains, or perhaps take a kayak out on the Stockbridge Bowl Lake.
Couple that with great restaurants, a vibrant cultural scene (music, arts and theatre) and numerous places of historical interest (Native American history, Shaker villages and ‘summer cottages’ of the rich and famous) and it doesn’t take long in the Berkshires to appreciate why they are so popular.
We stayed in a Guest House called the Devonfield Inn (see later) just outside the town of Lee, which was a great base for the things we wanted to see including the Norman Rockwell Museum in Stockbridge.
Lee, Massachusetts
High Lawn Farm
Pop into High Law Farm in the rolling fields above Lee to meet the resident dairy cows on this farm which has been supplying the Berkshires with milk since 1923. The dairy cows looked happy and healthy as they ate hay in the barn or tried out the back scratcher and walkthrough pen, like an amusement park for cows.
Then sample lunch from the on-site creamery, which offers fantastic artisanal cheese and charcuterie platters. We tried a grilled cheese, stuffed full of melted Brie equivalent and flavoured with mustard. Absolutely delicious.
For those who prefer ice-cream, you an buy the farm’s own ice-cream in a full range of flavours.
Café Triskele
Book dinner at the popular Café Triskele which offers French dishes such as escargot, Moules frites and steak frites. It was speedy service and delicious food.
Murals – look out for the pretty Welcome to Lee mural in town, and also the stars and stripes pedestrian crossing.
Stockbridge, Massachusetts
Norman Rockwell Museum & Studio
I have Lana del Rey to thank for my introduction to artist Normal Rockwell (naming an album after him). Coming from the UK, his work had not crossed my path, however Rockwell is one of America’s best-known artists and illustrators, working for the Saturday Post for 40 years, capturing elements of American life in his pictures, often with humour.
As the Civil Rights Movement evolved, Rockwell’s paintings became more political and so moved to Look magazine where he could be freer in his work. He produced an iconic series about Segregation and Integration which are so well regarded that they often feature in US school textbooks.
One of these paintings called The Problem We All Live With depicts six year old Ruby Bridges, an African-American girl being escorted to school by Marshalls for her own protection during the New Orleans school desegregation crisis in 1960. Weirdly, I was reading Travels with Charley by John Steinbeck on this trip which covers his visit to New Orleans and this exact scene on pages 189 – 207. His writing has stayed with me as it gives a very stark account of his findings.
He also painted The Four Freedoms series in the 1940s based on President Franklin D Roosevelt’s Four Freedoms State address identifying essential human rights – Freedom of Speech, Freedom from Fear, Freedom from Want and Freedom of Worship. All four of these paintings are on display in the Norman Rockwell Museum and they are incredible. It was hard not to be moved by them.
You can book a tour of his studio which sits in the Museum grounds. This is the original studio; however, it is not in its original location, having been moved from Stockbridge main street (literally cut in half, transported on lorries and reassembled). The studio was full of the props and trinkets he collected on his world travels, many of which appear in his paintings.
Rockwell lived from 1894 until 1978 and would have seen incredible societal changes throughout his life. He lived in Arlington, Vermont, before moving to Stockbridge, MA and painting a street scene of ‘downtown’ Stockbridge at Christmas – every year on 2 December, Stockbridge recreates his snowy scene, bringing in vintage cars and Christmas trees. What a lovely homage to Norman!
The town of Stockbridge
Stockbridge is a picture-perfect town with just a handful of shops and places to eat on a neat and tidy high street. Shops include the Stockbridge General Store, Country Store, Berkshire Bank, BerkCheers boutique, and many other craft shops.
The Red Lion Inn – Norman Rockwell used to live over the road from the Red Lion Inn and regularly popped in for drinks after he’d finished work. You can sit on the verandah and watch the world go by (slowly!), find a quiet corner inside the historic bar area, or find a table in the garden at the back.
Once Upon A Table – book a lovely dinner at the Once Upon a Table restaurant, conveniently situated next to the Red Lion Inn for after your pre-dinner drinks. The restaurant uses locally sourced foods where the dishes allow, and we enjoyed a tasty meal there – crab cakes, sea bass with mango salsa and berry crumble with ice-cream.
Native American history – Stockbridge was built on Mohican land and there are artefacts on display at Colonial-era Mission House and museum. This is a National Historic Landmark that tells the story of the Stockbridge Mohicans and missionary John Sergeant. A Mohican Walking Tour can also be booked.
Chesterwood
Chesterwood was the summer estate and studio of Daniel Chester French (1850–1931), the sculptor who made the statue of Abraham Lincoln for the Lincoln Memorial at the White House.
Lenox, Massachusetts
The Mount, Edith Wharton’s home and sculpture trail
Having read The Age of Innocence by Edith Wharton before coming to the Berkshires, I was keen to visit the home that she designed for her and Teddy her husband, having left Newport as they weren’t keen on the microscope of life there. Edith and Teddy lived at The Mount from 1899 to 1911.
The design was based on an Italian property in stunning white marble. She kept the home symmetrical with false doors and windows to keep the effect (only the servant quarters to the side throw off the symmetry). Best of all, the house is ‘at one with nature’, surrounded by tall pine trees and pretty garden views.
The house design deliberately breaks from the Gilded Age fashion of Newport houses and does not have a fancy entrance wall straight into a ballroom. Instead, guests to The Mount would be met (and vetted) by staff who would then show them to the upstairs Reception room where Edith and Teddy would be waiting to receive them.
They were married for 28 years but did not have children, instead keeping 4 to 6 dogs at any one time. Edith was the breadwinner and wrote over 40 books, including The House of Mirth. She was the first female recipient of the Pulitzer Prize for The Age of Innocence in 1921. Sadly, the couple were divorced in France (less scandal there) after she discovered he had embezzled $1.5 millions of her money to fund an affair.
They sold The Mount and Edith remained in France until she died. Having designed the house herself, she must have been very sad about this, as the house and gardens are stunning – far nicer, and more livable, that the Gilded Mansions in Newport.
Hilltop Orchards
Pop in to Hilltop Orchards to sample some orchard fresh apples, Apple Cider Vinegar donuts or cider.
Tanglewood
Tanglewood is an annual music festival taking place in the towns of Lenox and Stockbridge from late June to September. It becomes the summer base for the Boston Symphony Orchestra who play in an outdoor arena (the Koussevitzky Music Shed) set in large gardens filled with beautiful trees, with views across the rolling hills of the valley.
TIP – sadly, we didn’t book a performance early enough and so everything was sold out when we were in town. However, you can visit in the morning (for free) to stroll through the grounds whilst the BSO are rehearsing. People were bringing deck chairs and sitting under the trees, chilling out and listening to free music – lovely!
Shakespeare & Company
If you want to enjoy an outdoor performance of Shakespeare and contemporary plays, then head to the Shakespeare & Company theatre in Lenox.
In fact, the Berkshires is an area rich in cultural opportunities with several theatres close together including the Colonial Theatre in Pittsfield, the Unicorn Theatre, and the Playhouse in Stockbridge – great if you are in the area for a while, frustrating if, like us, you are passing through and not able to access all these amazing possibilities!
Further north in the Berkshires
Other ideas further north in the Berkshires, include:
- Arrowhead Farm, Pittsfield, MA – where Herman Melville wrote Moby Dick – guided tours are available.
- Hancock Shaker Village, Hancock, MA – a historical Shaker Community.
- Mass MoCA (Massachusetts Museum of Contemporary Art) in North Adams – sadly this was closed on the day we were in town (Tuesday).
When to visit The Berkshires
The Berkshires are a year-round destination, depending on the experience you are looking for:
- Summer season – Tanglewood music festival, outdoor theatre and picnics.
- Autumn/Fall – leaf spotting, maple syrup and cider, what New England does best.
- Winter – snow, skiing, and fresh mountain air.
- Spring – flowers and perfect conditions for walking.
We were travelling in the third week of July and had lovely warm weather in the mid 20s Celsius.
Where to stay in The Berkshires?
We stayed in the Devonfield Inn, just outside Lee, which we booked via Booking.com and it was perfect for our two nights in the Berkshires.
It’s a lovely old clapboard house surrounded by pine trees, with large lawns in front of the house to sit and enjoy the peace and quiet. There were communal rooms such as a lounge, TV room and kitchen with tea and coffee making facilities. There is also a lovely swimming pool at the property, which was very welcoming, as were the hospitable staff!
The Devonfield Inn served a fantastic breakfast each morning, which changed daily. I lucked out with banana and chocolate chip cookies one morning – tick!
The Berkshires is not very ‘rock and roll’ but it is the perfect place to get away from a more hectic pace of life and get back to nature. Make a date to visit the Norman Rockwell Museum and work everything else around it!
Heading back to New York or Newark on Route 7
If you have time as you head back to the airport, drive south on Route 7 to enjoy this quiet corner of northeast Connecticut overflowing with unique shops between Great Barrington and Sheffield (Antiques Alley).
We drove south to Great Barrington but then turned west on Highway 23, before picking up the Taconic State Parkway south, then finally west towards Shenandoah and Newark Airport
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