Berkshires MA: A Getaway For Every Season

Last Updated on November 29, 2022 by Editor

WHY GO: Arlo Guthrie’s Alice’s Restaurant, was set in the Berkshires MA.  Norman Rockwell lived and composed his iconic Saturday Evening Post covers here. Inexplicably, Herman Melville wrote Moby Dick at his home in Pittsfield, far from any sea. And Edith Wharton designed her ideal home in these rolling hills.

Food Truck garden downtown Lenox MA

In addition, you’ll find a 1700’s minister’s home in the woods, saved by a couple with Decorative Arts cred, and a mansion built for a Gilded Age heiress.

In the summer, Berkshires MA towns are jammed with Tanglewood and Jacob’s Pillow bound culture-vultures with elaborate picnics, garden music, and dance on their minds.

Grounds at The Mount open for hiking Lenox MA

But in the quiet off and shoulder seasons, many attractions are open and you can get a luxury room for a relative song. One such lodging, The Apple Tree Inn, has just been reborn as a center of indie music and excellent food.

The weather might be iffy, and snow might linger on lawns, but this Getaway to the Berkshire Region will warm your heart.

The perfect French Onion Soup Zinc Bistro Lenox

For a complete Western Massachusetts vacation add the Northern Berkshires towns of

North Adams MA  and Williamstown MA to your itinerary.

And for updated information on the area, check in with Visit the Berkshires.

Things To Do In The Berkshires MA

Norman Rockwell Museum exterior, Stockbridge MA

TOUR: Norman Rockwell Museum, Stockbridge

Norman Rockwell, who “chronicled the American Century as no one else did, with an eye for everyday drama and extreme attention to detail” was only 22 years old when he began creating covers for the Saturday Evening Post.

The Norman Rockwell Museum in Stockbridge MA houses the largest number of original Rockwell’s in the world, based in the town where he lived the last 25 years of his life. Visit to hear tidbits and background about the life of one of America’s most popular illustrators.

Ruby Bridges, Norman Rockwell Museum, Stockbridge MA

Explore the large scale original paintings of Rockwell’s iconic Four Freedoms (of Speech, of Worship, from Want, from Fear) based on FDR’s “inalienable rights.” The illustrations toured the country during WWII, famously raising $145 million for War Bonds – the most successful drive ever.

Rockwell’s Controversial Depictions

In the turbulent, racially divided 1960’s, The Post shied away from controversy. So Rockwell moved to Look Magazine, which was more than willing to print the artist’s bold portrayals of “Murder In Mississippi” and “The Problem We All Live With,” depicting Ruby Bridges’ historic walk to her just- desegregated school.

Stockbridge Main Street by Norman Rockwell, Norman Rockwell Museum, Stockbridge, MA

Rockwell was born in 1894 and died in 1978. He bore witness to both the first flight at Kitty Hawk and the Moon Landing – along the way illustrating Tradition and the Past while honoring the American Spirit.

Start your tour downstairs by watching a 12 minute video of Rockwell’s life in a room that displays all 323 of his Saturday Evening Post covers. Changing exhibitions of Rockwell’s work and of American Illustrators past and present provide new views several times a year.

Download the Museum’s App on your smartphone for audio tours, videos, photos and more to further enhance your visit. The scenic 36-acre campus offers trails and park benches, river views, sculptures by Rockwell’s son Peter, and the relocated historic art studio from the Rockwell’s former backyard.

Both Rockwell’s Studio and the Terrace Café are open seasonally (Memorial Day through late October). $20 adults, $10 students. Open Thurs-Tues, 10-4 year round and till 5 in season.

The Mount Edith Whartons home from backyard fountain Lenox MA

VISIT: The Mount, Lenox

Edith Wharton, author of The Age of Innocence, Ethan Frome, and The House of Mirth, was the first woman awarded the Pulitzer Prize for fiction. This was at a time when society women were expected to marry and oversee the home.

Wharton did oversee the home – the design and building of her own, The Mount, in 1902, based on the principles detailed in her influential book, The Decoration of Houses (1897).

Fountain garden at The Mount Lenox MA

The past few years have seen major improvements at The Mount. Wharton’s library has been restored – with many of her First Edition books. And, Wharton’s most-used rooms have been set up to reflect her specific quirks.

For example, Wharton believed that lighting over the dining table cast unflattering shadows on herself and her guests; so, her salle a manger features only wall sconces and candlelit tables. Also, Wharton aways ate with a dog bed at her foot. She, like the late Queen Elizabeth, wanted her pups close at hand (or foot in this instance).

The Mount walking trails Lenox MA

Perhaps the most exciting updates at the Mount are the extensive, and beautifully maintained formal French and Italian gardens behind the home, accessed via unique terraced grass steps. Though designed the way Wharton envisioned them, she never saw these gardens in her lifetime.

Grass steps lead down to formal gardens at The Mount Lenox MA

The gorgeous grounds are free to wander, and offer miles of trails, which explains the uptick in visitors during pandemic. Home open daily May-Oct 10-5. Weekends Nov. and Dec. 10-3 for Holiday Tours. $20 adults, free for children under 18.

Ventfort Hall exterior - Lenox MA

TOUR: Ventfort Hall, Lenox

In 1893, Sarah Morgan – sister of finance tycoon, J.P. Morgan – took $900,000 from the $3 Million that her father left her to build this 58-room, 28,000 sq. ft. Jacobean-style summer house, Ventfort Hall, close to downtown Lenox MA. As this was the “Gilded Age,” Sarah spared no expense – buying fireplace marble and Renaissance-era door frames from Italy, and furnishings from Europe.

Ventfort Hall grand entrance Lenox MA

The Westinghouses were neighbors, so the home was built with the latest technologies: electricity, telephones, and of course indoor plumbing and gas. The best money could buy. Sadly, Sarah lived only three years more – and died in 1896, leaving husband, George and three grown children: Caroline, George Jr, and Junius II.

Hallway in Ventfort Hall Lenox MA

Afterwards, Ventfort Hall rotated through a variety of owners and uses. Members of the Vanderbilt Family moved in for a time. From 1961 – 1977, it housed the Fokine Ballet Co. In the 1980’s a nursing home developer began interior demolition on the grand home. By then, the Ventfort Hall Preservation (VHP) group was formed to save the partially demolished building. In 1997 the movie, Cider House Rules, was filmed there, which must have provided a pop of cash to restore it.

Edith Wharton place setting Ventfort Hall Lenox MA

Upstairs, George Morgan’s sleeping chamber now serves as a museum. Currently, the room is set up for the 80th birthday of Giraud Foster, (owner of Bellefontaine – now Canyon Ranch). Among his 8 guests were Edith Wharton and her husband.

Sarah Morgan bedroom Ventfort Hall Lenox MA

Sarah’s room next door sports twin beds and fringed fuchsia chairs – a vignette drawn from photos of the home as it was when Sarah lived there. George’s Louis Vuitton steamer trunk, emblazoned with his initials, G.H.M., is down the hall.

Although you won’t find any original furniture in the cavernous ground-floor rooms, architectural elements have been restored to a certain extent. The stunning mahogany and oak woodwork and intricate wooden staircase remains intact.

Ventfort Hall carved staircase Lenox MA

Take a guided tour or ask for an audio tour to learn about the home, the family, and the ongoing restoration. It’s a mesmerizing look into the grandiosities and devil-may-care attitude towards spending, during the Gilded Age. Open year round daily, 10-4, $18 pp.

Bidwell House exterior Monterey MA

TOUR: Bidwell House, Monterey

For all you decorative arts and colonial-era architecture fans out there – the Bidwell House, 25 minutes from Lenox, is a sweet, hidden surprise. In 1760, Rev. Adonjah Bidwell moved to what was then the center of “Township #1,” which is now pretty much in the middle of rural woods.

Bidwell built this Georgian Saltbox in the Connecticut River Valley style, with additions put on in 1790 and 1830. Three generations of Bidwells lived here until 1850, when the Carrington family farmed and made charcoal for the Richmond MA Ironworks Co. From 1910 through the 50’s, the home cycled through an art school (hence it’s location on Art School Rd.), camp, and a retreat from the city.

Bidwell House red barn and gardens Monterey MA

Bidwell House Restored

In 1960, Parsons School of Design grads, Jack Hargis and David Brush, purchased the home with a focus on fabrics and textiles. They invested heavily in a historically appropriate restoration of the home itself. Using Rev. Bidwell’s inventory as a “shopping list,” they furnished the home with period appropriate pieces and added their own fabric-focused flair. The couple left the home as a museum upon their death. It opened to the public in 1990.

The Bidwell House is rare in that it sits on its original foundation and retains its original 1760 front door. The outbuildings, like the 1800’s red woodshed, are also original. Plus, the surrounding property has increased in acreage from 40 to 190 over three Bidwell generations.

Bidwell House dining room MA

Bidwell House Tour

A tour takes you through two floors of well-curated rooms. Docents point out the difference between the older Georgian-style parts of the house, with exposed beams, and those built in the Federal style (hidden beams, cleaner lines). You’ll learn about hallmarks of Queen Anne chairs (vase-shaped chair backs), and cabriole legs (curvy, flared out), and what heart-shaped peek-a-boo holes in interior doors mean.

Bidwell House interior Monterey MA

Hargis and Brush had a way with exhibiting their collections: displaying an array of Redware on shelves. “Bidwell would have been horrified to have people see these,” said my guide, Richard Greene. “These clay jugs were the Tupperware of the day.”

portrait of Mary Grey Bidwell at Bidwell House Monterey MA

Mary Grey Bidwell, Progressive Before Her Time

One of the most effecting stories, though, at least to me, was of Mary Grey Bidwell, wife of Rev. Bidwell’s son, Barnabas, who served in the Massachusetts legislature. A beautiful woman, Mary’s portrait hangs in the Best Parlor. When her lawmaker husband was in Boston, the two, like John and Abigail Adams, corresponded by letter.

And so, we have Mary’s thoughts in her own words. As did President George Washington, Mary had a very compassionate view of “The Hebrews.” In 1807 she wrote, The revolution in France will either in this, or succeeding generations, restore the Jews to Palestine, and render that despised people more respected.

She was also concerned about the “poor oppressed Africans,” considering slavery to be a “stain on the nation,” and implored Barnabas to vote with his conscience.

Bidwell House docent, Richard Greene, MA

More people learned about the Bidwell House during the pandemic, as curators started to offer lectures and programs on Zoom. By virtue of both this and the fact that visitors are invited to walk, bring their dogs, or, in season, X-country ski on six miles of bucolic trails, the Bidwell House has grown in popularity.

$15, Guided tours of the house run from Memorial Day (May 30) through early October, and are held on Mondays, Thursdays, Fridays, and Saturdays. Tours are available by appointment only and must be booked 24 hours in advance. Monday tours should be booked by the previous Friday. Email bidwellhm2@gmail.com to make a reservation. The grounds, and gardens are open daily, dawn to dusk, free of charge, and include a number of outdoor self-guided tours.

Naumkeag Gilded Age Mansion in Berkshires MA

VISIT: Naumkeag, Stockbridge

Built in 1884 on 48-acres, the Gilded Age Naumkeag was summer home to Joseph Choate, a prominent New York attorney and U.S. Ambassador to Great Britain, and his wife, Caroline. Designed by McKim, Mead & White, several generations of the Choate family lived in this a 44-room shingle-style home, until Mabel Choate bequeathed it to The Trustees in 1958. Open in season for tours, it’s best known for popular seasonal programming, like the Pumpkin Show and Winterlights. 

Flower box at Berkshire Botanical Gardens Stockbridge MA

VISIT: Berkshire Botanical Garden, Stockbridge

Stop to smell the roses and plenty of other blooming plants at the Berkshire Botanical Garden. In addition to lovely gardens, BBG offers classes and programming year round. Open May-Oct, $18, free on Tuesdays. 

WALK: Pleasant Valley Wildlife Sanctuary Mass Audubon, Lenox

This 1,000-acre Pleasant Valley Wildlife Mass Audubon Sanctuary now features a boardwalk that brings you up close and personal to muskrats, beavers, and other marshy animals (among many others).

Objectify Exhibit, Berkshire Museum, Pittsfield MA

VISIT: Berkshire Museum, Pittsfield

Considered a “Local Treasure,” the Berkshire Museum has been delighting and educating the surrounding communities and tourists alike for over 115 years. Melding science, nature, and art, you’ll stroll through galleries showcasing aquatic life around the world, birds and animals mounted in old-fashioned dioramas, and a large Paleontologist-in-training “dino-bone-digging” pit.

The Victoriana display, “Objectify,” dredges up a Sperm Whale jawbone, humanoid Chimp skeleton, a 2,300 year old Mummy in sarcophagus, and paintings and sculptures from storage – displaying them right upon the crates in which they were stored.

Hall of Innovation, Berkshire Museum, Pittsfield, MA

My favorite exhibit, and certainly a crowd-pleaser, is the Feigenbaum Hall of Innovation, which posits “All kids are born scientists and engineers,” and stresses, as Thomas Edison said, that  “Just because something doesn’t do what you planned it to do doesn’t mean it’s useless.”

Starting with the innovative iron plow that Thomas Melville (Herman’s dad) introduced at the 1818 Pittsfield Agricultural Fair, this gallery invites visitors to consider Unexpected Outcomes, Overcoming Obstacles, and How to Define Success in interactive ways.

In effect the Hall of Innovation reflects the collaborative spirit of past and present Berkshire’s innovators. $15 adults, $8 kidsMonday through Saturday,10 a.m. to 5 p.m. Sunday, Noon to 5 p.m. 

The Guthrie Center, Great Barrington MA

VISIT: The Guthrie Center at the Old Trinity Church, Great Barrington

Yes, Arlo Guthrie’s friend Alice, of  Alice’s Restaurant lived in this church. Now, it’s The Guthrie Center, an interfaith “BYOG” (Bring Your Own God) house of worship on the first Sunday of every month, and a community hall of sorts. Come for a free lunch (Wednesdays), free legal advice, a concert, drum circle, or other event. Just check the website for calendar offerings.

VISIT: Chesterwood, Stockbridge

Have you ever been curious about the man who sculpted the Lincoln Memorial?  Daniel Chester French was one of the most celebrated artists of his day. Chesterwood was both his summer home and studio. $20, adults, $10 children. May to Oct 10-5.

VISIT: Frelinghuysen Morris Museum and Studio, Lenox

Fans of modernist, abstract art will want to peruse the work and collection of Suzy Frelinghuysen and her husband George K. Morris. Visitors can see their work hanging beside that of the most famous Cubists of the day, including original Picasso’s at the Frelinghuysen Morris Museum and Studio. $20 adults $18 seniors for self-guided tour, Thurs-Sun 10-3  June 20-Labor Day.

Arrowhead, home of Herman Melville, Pittsfield MA

VISIT: Arrowhead, Pittsfield

Herman Melville wrote his masterpiece, Moby Dick, while living in his small bright yellow house, Arrowhead, right on a main road. Open daily from Memorial Day Weekend through Columbus Day. 9:30 am. to 5 pm. Tours begin hourly, with the first tour at 10 am. and the last tour at 4 pm. Tours are approximately 45 minutes long. Check website for tour dates and rates.

Railroad Street Shopping Dining area Great Barrington MA

SHOP/EXPLORE: Downtown Great Barrington MA

Railroad Street

The boomerang-shaped Railroad St. in downtown GB features numerous independent shops and restaurants, including the always-has-a-line SoCo Creamery,  Bizen Japanese Restaurant and Sushi Bar. And….

Railroad Street Collective Gallery Great Barrington MA

Railroad Street Collective

What began as a 2 month pop-up in November 2020 has become the permanent Railroad Street Collective. Ten local artist “residents” share time and pool their resources at this innovative art and gift shop. It’s clear that owner, Kristen Kanter, has a keen eye for some of the best craftspeople in the area, with wares that range from kids toys and clothing to eye catching, reasonably priced artwork.

Robins Candy Great Barrington MA interior

Robin’s Candy 

Much can be written about Robin Helfand’s MBA Corporate background, her stint at Dean & Deluca, and founding of her own specialty store in upstate NY. But suffice it to say, you come to Robin’s Candy for the vast array of sweets in a vibrantly colorful fantastical space.

Downtown Lenox MA

SHOP/EXPLORE: Downtown Lenox MA

There are art galleries, unique craft shops, and tony clothing emporiums galore in downtown Lenox. Our favorites include Concepts of Art-Lenox Judaica for the latest in Mezuzahs, and Purple Plume for artsy women’s clothing and accessories.

Stockbridge MA shops and restaurants

SHOP/EXPLORE: Downtown Stockbridge MA

Most of the gift shops, galleries, and restaurants in Stockbridge can be found on and around the block that the Red Lion Inn dominates. Be sure to walk down alleys where, in warmer months, you might just find an outdoor table set for 10.

Clemens Kalischer, Photographer, Image Gallery, Stockbridge, MA

Clemens Kalischer-owned Image Gallery

The Image Gallery has been located next door to the Red Lion Inn for years. Holocaust survivor and world-famous photographer, Clemens Kalischer died in June 2018 at the age of 97.

Kalischer left his German homeland in 1933 when his parents saw “the writing on the wall.”  Although he served as Norman Rockwell’s principal photographer, Kalischer was best known for his portraits of immigrants arriving in New York City from DP camps after the war.

Restaurants in the Berkshires MA

Zinc Bistro interior Lenox MA

EAT: Lenox MA Locals Recommend

Alta Restaurant and Wine Bar for New American, Brava for small bites Italian, Zinc Bistro for one of the best French Onion Soups on the planet; Pizzeria Boema for a quick salad or mozz and marinated veggie skewer; sweets at Mielke Confections; baked treats at Haven Cafe and Bakery.

Big Elm Brewing Taproom Great Barrington MA

EAT: Great Barrington Locals Recommend

Baba Louie’s for funky inventive pizza combos like the “Dirty Brutto” pie, piled with roasted red potatoes and roasted garlic. Number Ten – a “classic steakhouse” with some twists, and the new kid on the block, Big Elm Brewing Taproom whose neighbors include the very good Greek Aegean Breeze.

Where To Stay In Berkshires MA

Although there are tons of places to stay in the Berkshires, from B&B’s to franchise hotels, we present the oldest icon and latest sensation below:

Apple Tree Inn guest room with wood burning fireplace

STAY: Apple Tree Inn, Lenox

An old-fashioned hotel no longer, the Apple Tree Inn in Lenox is now the hippest place to stay in the Berkshires. New ownership, a renovation, great new chef, and live indie music four nights a week, this old-newbie is a Maven Favorite, and thus earned its own Apple Tree Inn review here.

Red Lion Inn Stockbridge MA

STAY: Red Lion Inn, Stockbridge

The Red Lion first opened in 1773 as a rough and tumble stage coach stop. It then evolved into a way-station for prosperous sojourners.  If original sloping floors could talk, they’d tell of the tens of thousands of guests who have wandered down these mazelike hallways filled with enough art, including that of hometown hero, Norman Rockwell’s, to make historians and museum-goers giddy.

Rockwell’s painting of Main Street Stockbridge in winter depicts an unlit, closed-up Red Lion Inn. From the mid-1860’s, when the Berkshires became a summer country escape for city folk, until the 1960’s, the inn was open only in summer tourist season.  Now, wintertime is prime time. If you visit when the snow starts to fall, you’ll see why.

First Impressions of Red Lion Inn

Stepping onto the wide white porch and through the door, you’ll be hit with a nostalgia not necessarily your own. Deeply colored upholstered Victorian chairs and couches face a blazing fireplace. A collection of teapots line shelves and cram crevices all around.

Lincoln Table at the Red Lion Inn

I nearly bumped into the “Lincoln Table” – from the old Union League Club of New York. It was bequeathed to long-time Red Lion Inn owner, Mrs. Plum, right after the Civil War. Charles Dickens and Abe Lincoln were purported to have dined on this very piece of furniture. Who am I to dispute this claim?

Service at the Red Lion is laid back –  the kind of nonchalance you’ll find in a rambling old hotel. It’s all good.  You’ll be attended to presently. But there’s really no rush.

Rooms at the Red Lion Inn

In the 1990’s the Red Lion had seen better days.  And then it was refreshed. Country Victorian with modern amenities, each room harks back to the time when city-folk came here for fresh air and homey ambiance.

Choose a room in the main inn or in one of the cottages just a block away – each with its own parlor and fireplace.

Widow Bingams Tavern Red Lion Inn

Dining at the Red Lion Inn

Burgundy carpeting, pewter plates and crystal chandeliers bring a turn-of-last-century ambience to the Main Dining Room.

Roast Turkey with Farmhouse Stuffing, Mashed Potatoes and Gravy is the comfort food signature, of course. But Quinoa Pasta With Harvest Vegetables is also quite delicious and would satisfy any picky vegan.

Not in the mood for a fancy meal? Order Yankee Pot Roast and Prime Rib “Popover” at the Widow Bingham’s Tavern. That’s also where you’ll find complementary coffee each morning, as well. Just the Facts: Rooms off season start at $109 per night. In season starts at $250.

Berkshires All Season Getaway Pin

Berkshires MA Pin

3 thoughts on “Berkshires MA: A Getaway For Every Season”

  1. Your article would be better named “Southern Berkshire County, Massachusetts: A Getaway for Every Season” since you’ve totally ignored everything north of Pittsfield. Northern Berkshire County is home to world-class art museums such as the Clark Art Institute and Mass MoCA, scenic gems such as Mount Greylock, countless hiking and biking trails, and many quality restaurants and lodging. While south county may have more internet sources to consult for such an article as yours, a little more digging would have produced a much more balanced piece.

  2. Hi DJ – Please re-read the introduction. There’s so much in Northern Berkshire County – I broke it out into two more posts and included links in the intro to this one. For a complete Western Massachusetts vacation add the Northern Berkshires towns of

    North Adams MA and Williamstown MA to your itinerary.

  3. HI Malerie – In response to your response to my comment above, I did indeed read the introduction to this piece and saw the links to information on North Adams and Williamstown – just 2 communities among many in the northern part of Berkshire County. That’s why I posted what I did. I stand by my comment that “your article would be better named Southern Berkshire County, Massachusetts: A Getaway for Every Season” since you’ve totally ignored everything north of Pittsfield in the information provided. It would make more sense to just call it that since that’s what you’ve written about.

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