Wölffer Kitchen, from the family that brought us the most beautiful (and Instagrammed) vineyard on the East End, is a must-visit for Saturday or Sunday brunch (try the Spiced Apple French Toast). The Beacon, one of the only restaurants directly on the water, is perfect at sunset. And LT Burger, a fun diner-esque experience, has been a favorite with locals for almost a decade. If you’re after a congenial feel where everyone knows each other by name, Dockside Bar & Grill is a good bet, with a heavy emphasis on seafood (and water views.) For a picnic, head to Cavaniola’s (Ina Garten’s favorite), pick up some sandwiches, and eat them by the marinas, watching the boats go by.
With some of the best interior design shops in the country quietly tucked off Main Street, you’d be remiss not to pop in and see what treasures you can bring back from your trip out east. Monc XIII, an industry favorite located on Madison Street, boasts an unbelievable array of mid-century pieces, as well as a unique and well edited assortment of home accessories. Bloom, also on Madison, is the epitome of “if you know, you know”; with no website, the store has one of the most comprehensive offerings of Astier de Villatte outside of Paris, as well as a gorgeous center garden and beautiful wares from France and Belgium. Interior and textile designer Katie Leede’s new shop (which overtook the old and beloved Ruby Beets location) is housed in what used to be a silent movie theatre—it also boasts a formidable selection of vintage furniture mixed in with contemporary pieces, as does Sage Street Antiques. Harbor Books, one of the most charming independent bookstores, will make you vow to never shop on Amazon again.
A recent addition to the Berkshires, 33 Main is a labor of love from designer Annie Selke, founder of the eponymous textile line and a native to the Berkshires. Named after its address, 33 Main is located at 33 Main Street in the heart of historic downtown Lenox, just minutes from Annie’s home and a short 20-minute drive to her company’s headquarters in Pittsfield.
With just eight rooms, the inn, housed in a historic, 4,320-square-foot, Federal-style building, is welcoming and intimate. The en-suite guestrooms—two of which are dog-friendly—feature Annie Selke headboards, bedding, rugs, lamps, furniture, and artwork that are all available for purchase through menu cards located in each room. The space feels new and fresh while still remaining inviting and supremely cozy.
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Guests are greeted with freshly baked cookies in each room along with bottled water, and a full gourmet breakfast is included each morning of your stay. Handmade herbal apothecary products are available in each bathroom, and a cocktail hour with nibbles in the front parlor gives off a joyous feel in the afternoons.
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