When it comes to summer travel—or any travel, really—we’re big proponents of the weekend trip. Sometimes a brief change of scenery is all you need to hit reset, clear your mind, and refresh your body after a long week. Luckily, there are plenty of fantastic destinations just a quick train or car ride away. Whether or not you get summer Fridays, it’s easy to make the most of your weekends with a little planning and preparation. Whether you want to eat well, shop at one-of-a-kind boutiques, sip wine on a vineyard, explore the outside, or delve into local history, you’ll find the right experience for you in one (or all!) of these five great escapes.
For Time Traveling…
Newport, Rhode Island
If your summertime fantasies involve sailing, clinking champagne flutes, and getting a taste of the Gilded Age life, a weekend in Newport is the trip for you. This idyllic New England town was the summer escape for late 19th- and early 20th-century America’s wealthiest tycoons.
Plan ahead and book a room at the Chanler at Cliff Walk, a twenty-room luxury boutique hotel in a turn-of-the-century mansion. It’s right on the famed Cliff Walk, a very Instagrammable 3.5-mile trail overlooking the Atlantic Ocean. The hotel’s Spiced Pear restaurant offers fine dining—lobster with truffles! seasonal soufflés!—in a refined ambiance with nice views.
When in Newport, there are two things you must do: cruise around on a boat and visit the mansions. Reserve a spot on the Rum Rummer II, a restored Prohibition-era rum-smuggling boat, or on sailing yacht the Madeleine. Of the many mansions, the best ones to visit are the Breakers and Rosecliff. The former is the grandest of them all, built by Richard Morris Hunt for Cornelius Vanderbilt II, whose family made a fortune building railroads. The latter is smaller but extremely beautiful, and served (along with another Newport mansion, the spectacular Marble House) as one of the backdrops in the 1974 Robert Redford-starring Great Gatsby adaptation. (That being said, Edith Wharton’s Age of Innocence—or the 1993 Martin Scorcese film—is a better look at the era that built these great houses.)
Around the wharf you’ll find plenty of boutiques selling preppy clothes, high-end bath products, gifts, and souvenirs. Enjoy a drink or meal at the 17th-century White Horse Tavern, a former haunt of pirates, sailors, colonists, British soldiers, and founding fathers.
Long Island’s North Fork
Forget the Hamptons—the North Fork offers natural beauty, a fresh sea air, and a relaxed pace without the crowds or hectic social scene. Long Island Wine Country has around 50 wineries—plus enough organic farms, cheese mongers, markets, and restaurants to keep you satisfied.
Start in Greenport—nearly at the eastern tip—and visit Kontokosta Winery. Brothers Michael and Constantine Kontokosta built the eco-conscious winery using recycled materials and reclaimed wood. Stay in the bright, airy tasting room or go outside for lovely views of Long Island Sound. Downtown Greenport has plenty of cute shops, restaurants, and places to stay, including American Beech, a breezy bistro with five all-white rooms.
You’ll want to linger at Croteaux Vineyards, the only vineyard in the US that exclusively makes rosé wines. Owner Paula Croteaux, who has lived in Paris and Provence, created a very French-style slice of serenity in the garden. Her crisp, refreshing, and sparkling rosés are the essence of summer in a glass.
When hunger strikes, head to Mattituck for two great options: Lombardi’s Love Lane Market for made-to-order panini and The Village Cheese Shop for picnic supplies, cheese plates, and fondues by former Brooklynite Michael Affatato.
Don’t miss McCall Wines in Cutchogue, one of the region’s few producers of pinot noir. Sample their delicate pinot and robust cabernet franc in the barn-turned-tasting-room and chat with owner Russell McCall and his son Brewster to learn how they saved the land from development.
The small town of Hudson, just two hours north of New York City, has officially emerged as a hotspot of design. It feels a bit like Brooklyn on the Hudson, thanks to spades of former New Yorkers who decamped there and set up shop.
A wealth of boutiques, restaurants, and bars are concentrated on Warren Street—Hudon’s main drag—so it’s easy to wander up and down, popping into stores that catch your eye. Score awesome mid-century modern finds at Neven & Neven Moderne. For handmade ceramics, candles, and paper goods stop by Flowerkraut. Peruse the vibrant local art scene, stop by Jeff Bailey Gallery for a reliably well-curated show.
Tired of shopping? Take a yoga class at Sadhana Yoga Center, then reward your efforts with a great meal at Fish & Game or WM Farmer & Sons. Locals head to Ör Gallery & Tavern for post-dinner drinks in a former auto garage with a cool Icelandic vibe.
Stay at the Rivertown Lodge in a former movie theater, opened by a hospitality industry vet who worked on high profile projects with Ian Schrager, but wanted to create a more earnest, down-to-earth hotel.
For the great outdoors…
The Berkshires, Massachusetts
For sweeping mountain views, hiking trails, small town vibes, and a dash of culture, it’s hard to beat the Berkshires in western Massachusetts. You’ll want a car for this trip, as things are a bit spread out.
Drive three-and-a-half hours north to Stockbridge and check into the historic Red Lion Inn. The place oozes old-fashioned New England charm, with rooms full of antiques and dainty patterned wallpaper. The dining room whips up a nice brunch and the subterranean Lion’s Den has live music every night. District Kitchen & Bar, a short drive away in Pittsfield, serves dependable pub grub, including giant bowls of hearty mac and cheese.
From Stockbridge, drive an hour north to hike Mount Greylock, the highest point in Massachusetts. There are plenty of different trails that will take you through the woods past streams and up to scenic vista points. While you’re in the area, don’t miss Mass MoCA, a major contemporary art museum in a former mill complex—it’s worth the trip just to see Sol LeWitt’s incredible wall drawings. In Lenox, you can visit the Mount, Edith Wharton’s former estate, and Tanglewood, the summer home of the Boston Symphony Orchestra, which boasts a great roster of outdoor concerts.
Though Philadelphia’s nickname is the city of Brotherly Love, it should be the City of Good Eats. There are so many amazing restaurants, you could design a whole weekend trip around meals and still just barely scratch the surface.
Take the train on Friday after work and roll into town in time for dinner at Zahav, where Israeli chef Michael Solomonov turns out mouthwatering mezze, including the silkiest hummus you’ve ever tasted, and tender lamb shoulder braised in pomegranate.