Escape To Series



Escape to: Southern Berkshires

By the Editors of Farewell Travels with Patricia Hubbard

New England weekend getaways

Photo courtesy of

Head up to the southwestern part of Massachusetts in the warm weather months, and you will quickly realize you are not the only ones that had the idea. These hills are well known for their cultural assets (Tanglewood Music Festival, Jacob Pillow’s Dance Festival) and rural beauty (sprawling farms, tidy little villages, dozens of lakes and ponds) and they attract visitors from around the world.

But in the chillier months (right through the winter), the Berkshire Hills are just--if not more--appealing.

Here’s what you need to know.
“Tiny Tim and Bob Cratchit (God Bless Us Everyone),” 1934, Norman Rockwell (1894-1978). Oil on canvas. Cover painting for “The Saturday Evening Post,” December 15, 1934. Private Collection. ©SEPS: Curtis Publishing, Indianapolis, IN.
Norman Rockwell and then some. You can feast your eyes and spirit on the 20th-century America memories captured by Norman Rockwell at the Norman Rockwell Museum which holds the world’s largest and most significant collection of his work, including paintings, drawings, photographs, letters and materials.

But that’s not all. In addition to the museum’s permanent collections, there are always wonderful temporary exhibits. In coming months, a special exhibit showcasing his interpretation of the holiday sAlex Ross, Mythology: Superman, 2005, courtesy of the artist, SUPERMAN, ™ & © DC Comics. Used with permission.eason called "Norman Rockwell: Home for the Holidays" (running Nov. 16 – Jan. 21) includes original drawings for Hallmark cards, paintings inspired by Charles Dickens’ classic story, A Christmas Carol, a point-of-purchase Coca-Cola Santa, and costumes and props featured in his artwork. Pictured here is “Tiny Tim and Bob Cratchit (God Bless Us Everyone)” 1934, Norman Rockwell (1894-1978). Oil on canvas. Cover painting for “The Saturday Evening Post,” December 15, 1934. Private Collection. ©SEPS: Curtis Publishing, Indianapolis, IN.

Also opening in November (on the 10th and running through Feb. 24, 2013) is "Heroes and Villains: The Comic Book Art of Alex Ross," one of the greatest artists in the field of comic books. (Illustration: Alex Ross, Mythology: Superman, 2005, courtesy of the artist, SUPERMAN, ™ & © DC Comics. Used with permission).

Take a hike. Two of our favorite Massachusetts hikes--Monument Mountain and Bash Bish Falls--are in the Southern Berkshires. At Monument Mountain, you can literally follow in thBash Bish Fallse footsteps of literary greats Herman Melville, Nathaniel Hawthorne and Oliver Wendell Holmes. All three hiked in these woods as young men. The trail system is a loop that starts at the parking lot and takes you up to the rocky peaks. Along Route 7 south of Stockbridge and a few miles north of Great Barrington, it’s easy to find.

Bash Bish Falls also holds a place in America’s creative past, as it has been a favorite subject of painters and photographers since the mid-19th century. The state’s highest single-drop waterfall, it has two cascades, shooting down some 60 feet. The falls are next to the 4,169-acres Mount Washington State Forest which has 30 miles of trails. Take a picnic in here on a crisp day and you’ll not want to leave. Bash Bish Falls State Park is accessible from Route 41 in the town of Egremont.

Stockbridge Christmas, New England weekend getawaysA Holiday Must. When choosing when to visit the southern Berkshires, consider the weekend of November 30th – December 2nd for this year’s annual Stockbridge Main Street at Christmas. The town, which was made famous by Norman Rockwell’s painting of the village, becomes a magical A Stockbridge Mainstreet at Christmas (Home for Christmas), Norman Rockwell Oil on canvas.” McCalls, December 1967 ©1967 Licensed by Norman Rockwell Licensing, Niles, IL From the permanent collection of Norman Rockwell MuseumNew England setting festooned with wreaths and lights.

Be sure to stay through Sunday, as the scene depicted in his painting (A Main Street at Christmas) is recreated complete with vintage cars parked in the spots in the painting. The festivities include horse-drawn rides, a visit from Santa, Roger the Jester and more.

Pictured right is A Stockbridge Mainstreet at Christmas (Home for Christmas), Norman Rockwell Oil on canvas.” McCalls, December 1967 ©1967 Licensed by Norman Rockwell Licensing, Niles, IL From the permanent collection of Norman Rockwell Museum.

A meal you'll remember. It’s pretty safe to say you’ll not find the likes of Great Barrington’s Gypsy restaurants in the Berkshires, new england weekend getawaysJoynt Café anywhere else in New England. Or anywhere else in the world. The ultimate family-run restaurant (not just mom and pop, but five kids, a son-in-law and three grandchildren are involved), serves everything from salads and pizzas to oven-baked Manzo Focaccia Burgers which are 100% grass-fed sirloin, chicken or homemade vegetarian lentil patties with a variety of accompaniments. Pictured here is the Yo, Adrian!, made with bacon, mozzarella, feta, sweetened pecans, avocado, mixed greens, tomato & Pear vinaigrette. Everything’s homemade and locally sourced.

There’s live music Thursday through Saturday night and an open-mike Wednesdays. Lunch and dinner are served all week long and on weekends, breakfast too. Seriously consider getting one of their Sweet Potato Pies to take back home. In fact, it makes a great addition to the Thanksgiving Day england weekend getaways

Oh no...really good ice cream. If you are watching your weight, don’t go near SoCo Creamery at 5 RailRoad Street in Great Barrington. In fact, don’t even go to their website. You will weep. In the summer months, there are lines down the street for the ice cream here which is in a league of its own with flavors such as Earl Grey Supreme, Crème Caramel and Salted Caramel. Need we say anything more?

Say cheese. Every time one of us travels through the Berkshires, we time it so we can have lunch at Rubi’s Coffee and Sandwiches at 264 Main Street in Great Barrington. There, you  can take your pick from a menu of grilled cheese sandwiches. The restaurant is right behind (and related to) Rubiner’s Cheesermonger and Grocers so you can count on a fabulous selection. On Friday and Saturday nights, they serve oysters and champagne along with a more robust menu.

On the slopes. Drawing skiers and Butternut ski areasnowboarders from Connecticut, New York, New Jersey and Massachusetts, Butternut Ski Area (near Great Barrington) is a good solid intermediate mountain. It also has a seven-lane tubing park, making it one seriously fun family winter playground.

Old but new. We always love to hear about historic buildings that come back to life and this is the case with the Monterey General Store, which just reopened in September after being shuttered for some time. It’s already the go-to place for great coffee and baked goods (also soups and sandwiches) for the residents of Monterey, which is 8 miles east of Great Barrington. While it’s full of old-fashioned charm (with restored woodwork throughout), it’s also very now with gourmet and local farm items.

Well, well, wellness! The fall and winter months are always a great time to push the reset button on your body – and one of our favorite places for this is Canyon Ranch health resort in Lenox. Whether you’re interested in fitness, preventive health care, nutritionCanyon Ranch, spas in new england  (including shedding a few pounds), spiritual growth or pure relaxation, the professionals here can personalize your stay to suit your needs. Rates are all-inclusive and cover accommodations, all meals (healthy snacks too), dozens of activities and classes (including yoga, fitness walks, hiking, tennis, athletic training) and use of all facilities. On top of that, every stay includes a generous allowance toward spa treatments (from classic massages to Asian therapies and Ayurvedic body treatments), sports instruction and integrative wellness services with caring experts.

Whatever time of year you visit, you’ll find plenty of opportunities to get outside and breathe in the fresh New England air and enjoy activities from kayaking and stand-up paddle boarding to snowshoeing and cross-country skiing. It’s the perfect vacation for mind, body and you.

Culture all year round. While you may want to come back to hear a concert under the stars at Tanglewood, you’ll also find the performing arts alive and well all winter long in the Southern Berkshires. Shakespeare & Company is in Lenox and The Mahaiwe Performing Arts Center is in Great Barrington. Check out their winter programs.

There’s no place like this home. Just over the border in Connecticut, you can stay in one of the few buildings in the northeaRock Hall, New England weekend getaways st designed by Addison Mizner, known as the “Architect of Palm Beach.” Rock Hall in Colebrook is a 10,000 square foot grand manor inn (built in 1912) on 23 private acres. It’s owned by Michael and Stella Somers, who have made it a truly luxurious retreat with  just five guest rooms all uniquely decorated with exquisite pieces and fabrics from Europe. Four of the rooms have wood-burning fireplaces and two have balconies. Breakfast and various snacks in the afternoon (including home-made gravlax) are prepared by Michael, who is the Chef du Maison. The owners can arrange a ride in a horse-drawn carriage through the autumn woods or over the snowy landscape in a horse-drawn sleigh come winter. It's a dreamy way to cap a day of exploring the nearby Berkshires.

Photo Credits: Thank you to The Norman Rockwell Museum, the Berkshire Visitors Bureau, and Ski Butternut who provided images for this page. All others were provided by the various property owners.



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