The Berkshires are a mountain range extending the western length of Massachusetts and spilling into nearby states. Sprinkled throughout the region are small towns and cities awaiting exploration. The Berkshires have it all – adventure, solitude, romance, culture, and more. Situated just a few hours’ drive from two major cities, New York and Boston, this area is pastoral but within reach.
With ample activity offerings and places to sightsee, it’s the perfect place to visit in New England if you’re looking for a charming and sophisticated getaway that’s remote yet accessible.
Traveling to the Berkshires from New York City is a scenic trip. The winding roads and getting off the beaten path is the perfect segue for your trip. The Berkshires is quintessential and friendly with excellent outdoor activities regardless of the time of year.
Fall is ideal to see the foliage with the peak season usually the second week in October. It is also a haven for weddings using nature and the rolling hills as a beautiful backdrop for your special day.
Staying at the Wheatleigh is a must. This 19-room estate is luxurious and welcoming. It was built by Henry Cook in 1893 as a wedding gift for his daughter. The grand entrance with the circular driveway and gorgeous fountain wraps you in opulence as you arrive. The property is sprawling and meticulously maintained and provides a sense of peace and serenity once inside estate. The views are spectacular from anywhere on the manor. You can enjoy the sculpture garden, heated pool, outdoor terrace or the lobby lounge and take in all the beauty. There is also a tennis court with the option to schedule a lesson with a local instructor. If you prefer to relax, schedule an in-room massage or book the terrace room on the second floor where you will be lulled by the sound of the entry fountain.
The level of service is as magnificent and adds to the experience before you arrive. Upon booking, you choose the amenities you desire. From the type of pillow to still or sparkling water in your room. There is a special homemade treat that awaits each guest when they arrive in their room. Your stay includes valet parking and breakfast. While there is a Nespresso machine in your room, coffee and tea are also served in the main lobby beginning at 7:30 am each day.
Located off the main lobby you will find The Protico fine dining restaurant. Chef Jeffrey Thompson provides an elegant tasting dining experience filled with seasonal flavors of the Berkshires. The weekly wine selection is paired with the Chef’s creations. It is not to be missed.
The Berkshires are an outdoor paradise and fill you with a sense of awe. Hiking is highly recommended during your stay. There are numerous guided hikes available as well as parks and trails you can enjoy on your own. The Berkshires will satisfy any craving for nature. Climb the highest peak in the state or take a more casual ride along a rail trail.
Lenox, Great Barrington, Stockbridge and Lee are all characteristically quaint towns comprising the Berkshires with art galleries, shops and restaurants.
Three recommendations in Lenox I particularly enjoyed:
*Haven, a great breakfast spot with delicious hearty entrees.
*Alta Wine Bar for a light lunch, pre-dinner or dinner with fresh homemade dishes and welcoming patrons.
*Scoop, to enjoy tasty homemade ice cream
If you would like to stay closer to main street area in Lenox, The Kemble Inn is a short walk from town. This gilded age mansion provides charming 9 rooms for its guests. Most of the rooms have fireplaces which add an extra layer of coziness. You feel right at home during your stay. Enjoy breakfast overlooking the scenic grounds and views of the mountains. I am delighted I was able to stay at the Kemble Inn before the current owner, Scott, sold it. The new owners will take over in November 2021 and continue to showcase this treasure. Under the current ownership, children 12 and over are welcome at the Inn.
Stockbridge was home to Norman Rockwell, an icon of 20th century American illustration art, for twenty-five years. Here, a museum was established in his honor in 1969. This temple to Rockwell’s work offers a deep dive into this life, highlighting his artistic growth, how he posthumously became the state artist of Massachusetts, and the societal impact of his popular illustrations. The museum is dedicated to equity, and it illuminates the connections between art and justice through its exhibits and programs.
Back in Lenox, The Blantyre, with its feel of a country estate, welcomes you like a family member. This luxury resort was built in 1902 and it set on 110 acres for guests to enjoy and explore. Settle in and enjoy the spa, tennis courts and other activities on the property and in the area. Whether you are looking for the perfect foliage trip, a summer get-a-way or you want to experience the holidays in a winter wonderland, Blantyre can accommodate all your needs.
Enjoy Café Boulud which highlights Chef Boulud’s take on the Berkshires. Enjoy the perfect wine pairing with your meal from the vast selection of an 8,000-bottle wine cellar on property.
There are three categories of rooms for your stay. The main house features luxurious suites and rooms full of history, character, and comfort. The Carriage House is a short walk from the Manor House, and provides a diverse selection of rooms and amenities close to the spa and pool. The Cottages are independent residences for those looking for a little more privacy.
Tanglewood is best known as the summer home of the Boston Symphony Orchestra. Situated in the beautiful hills of the Berkshires, it offers orchestral concerts and many other performances all summer long. With performances by the Boston Symphony Orchestra and the Boston Pops, as well as choral groups and popular artists, your visit will be a feast for the ears.
Hilltop Orchards is an experience. No matter the time of year you visit, you’ll be in for fun, good eats, savory sips, and an engaging time all around. Hilltop Orchards is committed to sustainable farming practices. Visitors can take a walk through the orchards or the property’s trails, pick apples seasonally, and participate in a cider or wine tasting at Hilltop’s Furnace Brook Winery. Be sure to swing by the farm store for the best apple cider donuts, seasonal produce, cider and wine, and other local goods.
A long weekend is the perfect length of time to enjoy the Berkshires. Many have gone for a long weekend and ended up buying a vacation home there after they fell in love with the charming area.
Away With Donna contacts who book Virtuoso rates through Classic Travel will receive free VIP benefits. These extras may include: room upgrade, daily breakfast, spa treatment, resort credit, early check-in or late check-out. Click here to book your hotel online at Classic Travel
