Perfect Long Weekend Destinations Just Outside New York City

Whether you want culture, nature, fine dining, or classic R&R, these are our top destinations for a totally charming getaway.

Town & Country
Written by William Li
October, 2020

Sweater weather is here, and it’s the perfect time to hit the road and take in the beauty of the autumn season. Nowhere is the foliage more spectacular than the Northeast. Whether you’re taking in the crisp fall air overlooking the Hudson River, hiking the majestic Berkshires Hills, or strolling the picturesque New England towns of Litchfield County, these three itineraries will send you on your way to the perfect long weekend.

Photo Credit Kara Thornton

Long known for its cultural offerings, The Berkshires—the Massachusetts county that stretches from Williamstown in the north and Great Barrington in the south—shines brightest in the fall when its eponymous hills are ablaze with autumn color. Situated in between Boston and New York City, the Berkshires offers scenic landscapes, pastoral hikes, and an abundance of culture and art.

Where to Stay

The Inn at Kenmore Hall is a stunning country inn in Richmond, Mass., situated on 20 acres of woodlands, orchards, and gardens, with spectacular views of the rolling, green Berkshire Hills. Owned and operated by J.Crew’s former head of menswear, Frank Muytjens, and artist/entrepreneur, Scott Edward Cole, the 1792 building has been transformed into a luxurious and stylish oasis with wood burning fireplaces in each room and decoration that artfully blends modernity and antiquity. And in true bed and breakfast style, guests wake up to a scrumptious morning meal in a candlelit dining room with a roaring fire burning. Rooms starting at $450.

A stay at the Granville House, an intimate five-room inn within a historic 1825 house in Great Barrington, Mass., is like visiting your coolest friend’s country home. The innkeepers, Terry and Terri Coughlin, alumni of Danny Meyer’s Union Square Hospitality Group, have created a deeply personal space with an eclectic mix of period antiques, mid-century modern furnishings, inspiring artwork, and thoughtful personal touches. Guests are treated to a relaxed kind of luxury including a jukebox and pool table in the parlor and rocking chairs on the large wraparound porch. And true to the inn’s commitment to being a good neighbor, Granville House is reinvesting a portion of proceeds to various organizations that support the special needs community in the Berkshire region. Rooms start at $200.

What to Eat

Michelin-starred chef Daniel Boulud has brought Café Boulud, his beloved Upper East Side institution, to Blantyre in Lenox, Mass. As one of the original 12 Gilded Age mansions in the Berkshires, this Relais and Châteaux property makes the perfect backdrop for the menu of autumnal French-inspired classics with a seasonal focus on ingredients from local farms, vegetable-driven creations, and Asian and Middle Eastern flavors.

Mark Firth left Brooklyn, where he owned the legendary Diner and Marlow & Sons, for Great Barrington, Mass. to open The Prairie Whale, an excellent farm to table restaurant that takes full advantage of the region’s farmers, cheesemakers, and foragers. The extra crunchy fried chicken and the impossibly fluffy pancakes are both best in class. As are the Bloody Marys.

The charming tapas bar Brava in Lenox offers a comprehensive menu of Spanish small plate classics such as Shrimp in Garlic Sauce, Patatas Bravas, and Grilled Lamb Chops in addition to excellent salads and hand-made pizzas. Proprietor and world-class oenophile, Whitney Asher, will happily guide you through the award-winning wine list of over 100 wines, 40 of which are available by the glass.

Located on Main Street in storybook Stockbridge, Mass., The Red Lion Inn has been welcoming guests since 1773. The iconic historic inn is quintessential New England and having a cocktail or a mug of hot cider on its front porch is an absolute must after a day of leaf peeping.

What to Do

The Clark, a well-respected museum set on 140 acres of beautiful landscape, is home to an extraordinary collection of European and American paintings, sculpture, prints, drawings, photographs, and decorative arts from the Renaissance to the early 20th century with particular depth in the works of American masters Winslow Homer, George Inness, and John Singer Sargent. In addition to the classical white marble main building from 1955, the campus includes a stunning addition with a reflecting pool from Japanese architect Tadao Ando. Ground/work, the museum’s first outdoor exhibition of site-specific installations, is free to the public, and not to be missed.

Hancock Shaker Village is a must-visit destination of 750 acres, 20 historic Shaker buildings, and over 22,000 Shaker artifacts that demonstrate the history, industry, life, and traditions of the Shakers and their achievements and contributions to the American way of life and design history. Standouts include the magnificent 1826 Round Stone Barn and the 1830 Brick Dwelling.

Edith Wharton’s legendary home, The Mount, is a master class in classical architecture, landscape design, and interior decoration. A tour of the house, gardens, and fifty acre grounds will give visitors a taste of Gilded Age life and also a dramatic view of the Berkshire foliage fireworks.

Where to Shop

Charles H. Baldwin & Sons, a 133-year old family business, is known for its famous Madagascar Vanilla extract. The historic shop in the charming village of West Stockbridge, Mass., is stocked with other signature items such as their Maple Table Syrup, Bloody Mary Mix, and Worcestershire Sauce, as well as specialty baking items.

McKimmie Co., a home & lifestyle shop in Lenox, Mass. specializing in imported textiles, apparel, and unique home accessories. The colorful and cozy selection of throws and blankets from Scotland, England, and Ireland are perfect for fireside lounging this fall.

Matt Rubiner is a cheesemonger extraordinaire and his Great Barrington shop, Rubiner’s, is beloved by major foodies such as Town & Country contributing editor Ruth Reichl, for its encyclopedic selection of cheeses, charcuterie, and specialty food items from around the world. The shop also features an equally well-rounded offering of natural wines and artisanal beers making it the perfect spot to go if you are looking for a picnic to bring on a hike or a tasty souvenir to take home.

Twigs, a boutique with locations in Lenox and Great Barrington, perfectly captures the laid back vibe of the Berkshires. From flowy Ulla Johnson dresses to the chic classic basics from Nili Lotan, Twigs is a one-stop shop for all your fall weekend wardrobe essentials.