Driving Time from Poughkeepsie: 1 hour 25 minutes
Weekend Rates: from $185 per night;
Five years ago, British expatriates Richard Proctor and Clare Weatherall purchased this tired ’60s roadside motor inn and reimagined it into a hip motel/bed & breakfast hybrid—infusing it with European sensibilities and charm (furthered tremendously by their homemade scones and granola on offer as part of the Briarcliff’s daily breakfast). Decorated with soothing sky and earth tones, the rooms are furnished in a rustic-chic motif, and the grounds have been lushly landscaped and outfitted with a dramatic, eye-catching firepit to gather around after dark.
The property is located at the base of Monument Mountain, a popular hiking destination, and sits on the northern outskirts of Great Barrington, the social and commercial hub of the southern Berkshires. Its outside-of-town location and positioning far back from the road ensures its guests absolute peace and quiet—and jaw-dropping stargazing—at night. Situated on Route 7, the main corridor of the Berkshires, the Briarcliff is only minutes away from the region’s other popular towns, including Lenox, Lee, and Stockbridge.
|Follow in the footsteps of luminaries Nathaniel Hawthorne, Herman Melville, and Oliver Wendell Holmes by hiking 1,642 feet to the top of Monument Mountain, where spellbinding views of the southern Berkshires foliage await.|
|From Great Barrington, take Route 183 north to Lenox. The road is canopied by trees and wends around the Housatonic River.|
|Once in Lenox, turn from Route 183 onto Richmond Mountain road to reach Olivia’s Overlook, which offers a breathtaking vista of Stockbridge Bowl (aka Lake Mahkeenac) and the surrounding valley.|
Venture north to Stockbridge, longtime home to Norman Rockwell and now home to the Norman Rockwell Museum, the largest collection of the artist’s works (many of which feature local residents and locales). Tip: It’s worth paying the additional fee for the self-guided audio tour, which is narrated by Rockwell’s son.