The Berkshires

Autumn conjures up thoughts of cozy, crisp, fire-side evenings and leafy, color-filled morning walks. Every city dweller yearns to leave the concrete jungle and truly enjoy this picturesque conception of the fall. Nestled directly between two metropolises, Boston and New York, lies a perfect escape where such visions are realized – The Berkshires. The Berkshires attracts people not only for its cultural and autumn-driven activities, but also for the luxury hotels and restaurants.

The Blantyre | 16 Blantyre Rd, Lenox, MA 01240, United States

Tucked in the Berkshire Hills, The Blantyre is a beautiful, Tudor-style country manor that offers all of its guests an unparalleled hospitality experience. Visitors of this Relais & Chateau institution transport themselves to Scotland, as they enjoy tea or a cocktail by warm fireplaces in the hotel living room, which walls boast taxidermy and portraits of dwellers from the past. For those individuals who opt to venture outside and experience all that is autumn, The Blantyre offers a vast array of activities such as fly fishing, hikes on its forty-six-acre property, golf and horseback riding.

The Wheatleigh11 Hawthorne Rd, Lenox, MA 01240, United States

Leading Hotels of the World property, The Wheatleigh combines personal service and extraordinary cuisine with the elegance and comfort of the 21st century. The Wheatleigh is situated on twenty-two-acres of property, allowing guests to venture outside and relish all that the fall has to offer. Following the outdoor activities, guests return to luxurious comfort, where they are pampered as they watch the rolling hills of The Berkshires by an outdoor fire pit.

The Mount, Edith Wharton’s Home2 Plunkett St, Lenox, MA 01240, United States

The Mount served as the late Edith Wharton’s country haven. Today, this colonial mansion operates as one of The Berkshire’s most popular cultural tourist sites. Visitors can enjoy the gardens, literary round table chats, jazz evenings, and special history exhibits every year from May to October. October, of course, invites spooky Ghost Tours in the evening Friday nights.


Great Barrington Farmer’s Market314 Main St, Great Barrington, MA 01230, United States

The Great Barrington Farmer’s Market offers the best local produce in the region. Throughout October, attendees will not only experience delicious pumpkin pies and butternut squash soup, but also enjoy family time in the charming Massachusetts town. Great Barrington Farmer’s Market will conclude its 26th season at the end of the month.

Hudson-Berkshire Beverage Trail

For those that are not the designated drivers to The Berkshires, we have found the perfect pit-stops for you. The Hudson-Berkshire Beverage Trail functions as the premiere beverage trail in The New York State and Hudson Valley. With numerous distilleries and farms on the trail, one will find a plethora of not only award-winning wines, beers, and spirits, but also produce, artisanal cheese, and baked goods. Some trail members include Brookview Station Winery, Harvest Spirits, and Berkshire Mountain Distillers.

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