Upon arriving at the Staveleigh House something deep within you immediately gives out a sigh of relaxation. A quaint, 2-story bed & breakfast, tucked into the sweetly sleepy streets of Sheffield, a tiny town in the heart of Massachusetts’ Berkshires region, the Staveleigh charmingly encompasses everything that New York City is not. Quiet, almost reverently hushed at times, country-style serenity permeates throughout–from the flowers overflowing on the front stairs, to the clean open kitchen in the back, where a homemade cookie or muffin might be found waiting for a hungry guest.  “Help yourself” cry out those tasty treats, and what makes the Staveleigh so special, is that you would never feel naughty caught with your hand in the cookie jar–instead, though you might blush at how many you’ve eaten, you would just be encouraged to have more, and enjoy!

The main reason for this extremely welcome, “be at home” feeling is the vivacious warmth that proprietor, Ali Winston, infuses in every aspect of the Staveleigh.  So genuine is her enthusiasm for your arrival, your breakfast choices (oh my! the breakfasts!), your itinerary, that you actually get swept up in your own delightful plans.  And of Berkshire plans: there are so very many to be had!  Be it antiquing in Sheffield and the nearby Great Barrington, or taking in the local music and culture, or (our favorite) exploring the vast natural landscape.  When prompted, Ali will let you in on secret swimming holes and the most scenic routes to take.

Every detail of the Staveleigh house is abloom with quirky antique artfulness, and though the whimsical demeanor nods towards the days of yore, Manhattan type A’s can stop sweating: highspeed internet does, in fact, grace the ether of this estate!  What doesn’t grace it is any hint of stuffy snootyness, impatience, or pretense.  Take the time to let Ali introduce you to her beloved menagerie of wooly mammoth-like dogs, goats, ponies and a mule (there is a small, fenced field and old, red barn behind the house).  After all, the eggs, perfectly scrambled on your breakfast plate, are from her chickens, the basil, from her garden.  And as you take it all in, you sigh and think: This is why you leave New York for the weekend.

Thankfully, it’s only a 2 hour drive and then you are free of the rat race that New York can feel like!  Free to open up to the embrace that is the Staveleigh.

Ava Fedorov

Photographs by Jeff Owens for Socially Superlative