The Design Lover’s Guide to the Loveliest Northeast Road Trips

It’s autumn in the Northeast, which means electric-hued foliage and crisp, invigorating air. From Long Island’s seaside charm to the mountainous corridors of Massachusetts, over to the pastoral Connecticut countryside and beyond, weekenders are in for a treat. Now’s an ideal time to explore the region’s rural integrity, with a flurry of outdoor endeavors and seasonal (socially distanced) eating and drinking—and escape the uncertainty of these times.

NORTH FORK, LONG ISLAND

There’s much to explore in the North Fork, 75 miles east of New York City, a bucolic stretch of fertile farmland, celebrated vineyards and laid-back farmstands.

What to Do

First you feast. Over the summer, NYC chef John Fraser reopened the veteran mainstay North Fork Table & Inn. With the inn portion forthcoming, the restaurant—a polished meld of reclaimed oak, creamy hues, and soft textiles—serves hyperlocal plates with produce from the nearby biodynamic farm, KK’s. For a casual affair, procure a bar seat and order the roasted kuri squash with a glass of Paumanok Chenin Blanc. Down the road in Greenport, 1943 dishes out wood-fired pies—try the famed clams casino (fresh clams, bacon, green peppers, and garlic). Set in an old bait and tackle shop, Little Creek Oyster Farm & Market shucks local briny oysters with water views. You can also gorge on lobster pot pies at Southold Fish Market. For the ultimate picnic, stock up on provisions from local outposts like Sang Lee Farms, 8 Hands Farm, Hallock’s Cider Mill, Kate’s Cheese, and the legendary Briemere Pies (which makes a wicked buttery apple crisp with stewed ’n’ spiced local apples).

With almost 60 wineries, you certainly won’t go thirsty. “We have an incredible wine country in our backyard. And, over the last 10 years, the area’s really hit its stride,” says master sommelier Laura Fiorvanti. Among her favorites are Lenz Winery, Paumanok Vineyards, McCall Winery, and the long-standing, family-run Macari Vineyards, also committed to organic and sustainable winemaking.

Meanwhile, the sweet farmstand Morning Sun stocks local apples, sea salt, and handmade Moroccan plates. In Southold, White Flower Farmhouse, a French cottage–inflected boutique, sells linens and antiques. For neutral-colored linen robes, beachy scented lotions, and furry slippers, drop in Rica Bath & Body. Looking for some nautical history? Thumb through the well-worn classics at Burton’s Books.

On Peconic Bay, both South Jamesport Beach and Orient Beach State Park are ideal for biking, hiking, kayaking, and picnicking. Additionally, weekenders should explore the Peconic Land Trust; whose robust programming includes sailing, fishing and bird-watching. For Instagram moments, visit the tranquil Goldsmith Inlet, running from the beach to a tranquil saltwater pond with ospreys. Alternatively, a 10-minute ferry from Greenport ushers you to Shelter Island’s hidden secret: Mashomack Preserve, a low country–esque network of trails featuring tidal creeks and salt marshes.

Where to Stay

For throwback seaside lore, the low-flung 55-room Sound View is kitted out in nautical and midcentury pieces with windows framing the azure waters. Come mealtime, gather inside the minimalist A-frame Halyard for chef Stephan Bogardus’s luscious local seafood plates—grilled Montauk swordfish and Shinnecock sea scallops with chanterelle mushrooms (and, if you’re so inclined, shaved truffles)—washed down with buzzy cocktails and epic sunsets.

HUDSON, NEW YORK

Once a bustling whaling hub and an international trade center, the river town of Hudson maintains a unique mix of architecture (Greek, Victorian, federal, colonial), serving as a home base for hip design stores, fashionable boutiques, and culinary delights.

What to Do

In the mornings, Kitty’s Market serves a small menu of breakfast sandwiches and fresh pastries, while Breadfolks is the place for organic sourdough loaves, danishes, and banana cream canelés. Just down the way, the folks behind the wildly popular Lil Debs Oasis have opened a vegan pop-up called Fuego 69 (inside the Rivertown Lodge) known for its buckwheat flatbread with a tahini-miso-scallion spread. Additionally, the lodge’s Tavern doles out heaping comforts à la grilled pork ribs with preserved mustard greens and anchovy. For mushroom tacos and chopped salads, pop by the historic Barlett House (and save room for the espresso milkshake). In Germantown, Otto’s Market serves chef Bobby Hellen’s elevated deli fare (broccoli melts with fennel, goat cheese, and chile flakes) and grab-and-go groceries.

Down the road, you’ll find chunky Japanese knits and Astier de Villatte candles at the well-curated Alder. Back in town, the Quiet Botanist headlines niche apothecary brands (Osea, Alder New York) and heavenly-smelling dried herbs and flowers. Of course, vintage finds are seemingly everywhere: Finch stocks midcentury furniture; Red Chair on Warren carries global pieces (Swedish, French and Belgian); while Antique Warehouse houses, truly, everything under the sun. For curated LPs, shop at John Doe Records, then browse book titles at the Spotty Dog (you can also sip beer and coffee here). Wind down with seasonal ales at Crossroads Brewery or the funkier, to-go-only Suarez Brewery.

Carve out a few hours at Art Omi, a family-friendly not-for-profit site, whose lush 120 acres feature contemporary sculptures by artists Rob Fischer and LevenBetts Zoid. Later, soak up some nature at Olana, a late-19-century garden and house—complete with Moorish accents— and built by American landscape painter, Frederic Edwin Church. For an easy wooded hike, High Falls passes by two picturesque waterfalls; there’s also ample bird watching. In town? Head for a sunset jaunt to Promenade Hill and stroll along the Hudson River.

Where to Stay

Everything has a story at the Maker, a new, intimate hotel by Fresh Beauty founders Lev Glazman and Alina Roytberg. An homage to designers and artists, three historical buildings showcase different periods—industrial, Belle Epoque, and Art Deco. The 11-rooms feature handmade beds from Portugal, and bathrooms (some featuring soaking tubs) are outfitted with the duo’s bath products and Italian linen robes. There’s also a moody cocktail bar, and a leafy jewel-box conservatory functions as the on-site eatery, offering rustic handmade pastas and grilled meats.

WASHINGTON AND NEW PRESTON, CONNECTICUT

The rural pockets of Connecticut lean heavily on quaint village sensibility, filled with plenty of outdoor trails and shops stocking stylish gear, furniture, and artful pieces.

What to Do
In Washington, Community Table serves cool-weather eats—smoked beets, grass-fed burgers, and pumpkin curry. Don’t leave without nabbing pantry staples: bluefish pâté, sourdough brioche rolls, and bottled house vinaigrette. For a diverse spread (think thin-crust pizza, salads, and fruit pies), check out the Pantry; the casual cafe Marty’s whips up coffee, grilled paninis, and sweet treats. Set in a circa-1850 colonial home with a flagstone patio, the charming, locally loved GW Tavern doles out hearty salads, crab cakes, and grilled meats.

For shopping in New Preston, Plain Goods has cashmere sweaters, teak spoons, and bespoke chocolates. You can find local tees, totes, and handcrafted wooden dream boxes at Five Janes or glance at the latest titles at Hickory Stick Bookshop. In Washington, George Home carries a global mix of midcentury furniture, pencil drawings, and artful objects, while the Privet House stocks George Jensen pieces, rattan baskets and Belgium soaps. Art aficionados enjoy Washington Arts Association & Gallery, a nonprofit founded in 1952, known for emerging and establish artists, including Alexander Calder and Andre Masson.

Choose your own hiking adventure around Steep Rock Preserve, spread over 998 acres and known for its kaleidoscopic vistas of the Shepaug River Valley. You can also explore a 235-foot curved tunnel in Steep Rock Ridge, hand-chiseled by miners in the late 1800s. Alternatively, take in the striking milieu by horseback. On the outskirts of town, walk the trails of Hidden Valley Preserve popping with earth-toned meadows and densely wooded, amber-crimson forest.

Where to Stay

Situated on 58 acres, the 35-room Mayflower Inn & Spa, Auberge Resorts Collection, is spread across three buildings. “I looked to the great English and Scandinavian country houses and also to their gardens,” says designer Celerie Kemble, whose decor features a swell of four-poster beds, sisal carpets, Turkish rugs, and Gustavian antiques. Stroll the Shakespeare garden, relax in the spa, or browse the whimsical boutique (we recently spotted a French wooden birdcage and a Dale Goffigon photo). In the kitchen, NYC chef April Bloomfield hosts a hearty autumnal spread: grilled heritage pork loin and cider battered flounder. Afterwards, huddle around a toasty bonfire for s’mores and digestifs.

BERKSHIRES, MASSACHUSETTS

Dazzling blue skies against scenic byways, lush valleys, open pastures and mountains—it’s no secret this New England region helped write the guidebook on fall.

What to Do

For a morning spread of croissants, doughnuts, egg sandwiches, and coffee, check out the local’s favorite Southfield Store. Nearby, the old-school Prairie Whale smacks of Brooklyn-cool lunch classics: grass-fed cheeseburgers and fried chicken. Across town, the barn-style dwelling Cantina 229 serves wood-fired curried scallops while an outdoor lawn doubles as a place for games and bonfires. Minutes away, taste Hudson Valley foie gras and pan-roasted squab at the warm, candlelit Old Inn at the Green.

In Great Barrington, create your own picnic with wine, cured meats, and high-end cheeses from Rubiners. A few doors down, peruse the latest fiction titles from Book Loft, then pick up hand-poured candles from Hammertown. These days, you’ll also find blissfully legal cannabis provisions at Theory Wellness. For chic jumpsuits and Malin & Goetz products, check out Griffin, and later, roam the home goods selection at both Germain and Painted Porch. In Lenox, Sienna Patti Contemporary houses a smart collection of jewelry while the nearby Design Menagerie hawks Bensimon sneakers and rubber boots.

Surrounded by elegant gardens and stables, wander the quiet grounds of novelist Edith Wharton’s former estate, the Mount. Alternatively, stretch your legs along the Pleasant Valley trails or make the three-mile loop at Monument Mountain offering views of Squaw Peak. You can also saddle up for horseback riding at Sunny Rose Farm. There’s no shortage of art—the industrial sprawl of Mass MoCA hosts James Turrell and Sol DeWitt, and in Williamstown, the Tadao Ando–designed Clark Art Institute remains a bastion for 19th-century French paintings, including 32 works by Renoir.

Where to Stay

In August, Hyatt’s venerable wellness brand Miraval opened its third location in Lenox, Massachusetts. Situated on 380 acres, the restful cottage-style rooms are dressed in warm cranberry, navy, and amber. Relax inside the expansive spa, whose wellness menu includes a 90-minute reiki session, a 60-minute organic Tulsi rose facial, and an indoor pool. You can also enlist in the resort’s famed equine program or try your hand at beekeeping.

LIVINGSTON MANOR, NEW YORK

Welcome to Sullivan County, the southwest pocket of the Catskills, once known as the Borscht Belt (memorialized by the 1987 film Dirty Dancing) and beloved for its sleepy charm, ample fly fishing, and craft breweries.

Commence your sojourn with a pilsner at the modern chalet-style Upward Brewing Company, hosting a smattering of picnic tables and overlooking a small mountain (you can also hike the grounds). Nearby, Catskill Brewery couples its suds with tacos courtesy of the Catskills Food Truck. Highlighting the local bounty, the wood-fired shrine Kaatskeller serves its pizza (wild boar pepperoni, wild ramp kale pesto) with hard cider and cocktails. Meanwhile, the cozy, wood-and-stone-paneled Arnold House Tavern whips up memorable kale salads and fish and chips.

Part meat counter, part mercantile, Van Smokey’s also hawks the brand’s delightful homemade beef jerky, spicy Bloody Mary mix, and hip java newcomer Spanky’s cold brew. Snag fresh produce, farm-bottled milk, and on-tap kombucha at Main Street Farm, and later visit the hippie-flared Sunshine Colony for salty bites and natural wines compliments of Upstream Wine & Spirits.

For mountain life essentials, the small but mighty Homestedt Design carries stylish Swedish Stutterheim Raincoats and Buck Brook alpaca wool. Nearby, the vintage emporium Taylor and Ace displays its teak bar carts with taxidermy, while Long Weekend sources vintage pieces from nearby estate sales. For chic kitchen wares and ceramics, drop by Sunrise Ruffalo’s namesake Sunny’s Pop. There’s also Nest, the popular Scandi-flared boutique from a former Vogue editor. Elsewhere, the revamped Catskill Fly Fishing Centre and Museum hosts exhibits and a trail network along the Willowemoc River; they’ll also help you set up a lesson.

When nature calls, Neversink Unique River Area offers low-key treks, passing by a trio of waterfalls. Tusten Mountain Trail snakes along stone archways and winds up with enticing views of the Delaware River while the easy Frick Pond Loop travels through scenic forest and wetlands. For fly fishing, gather by Junction Pool, where Willowemoc Creek meets Beaver Kill; and for anglers seeking out brook trout (a.k.a. “brookies”)—Crystal Lake is terrific.

Where to Stay

Once a clapboard boarding house, the recently reimagined Kenoza Hall (from the folks that brought you the woodsy Arnold House) dresses its 22 rooms with sleigh beds, custom wallpaper, and a meld of reds, grays, and pinks. Other diversions include a full spa, a heated outdoor pool, walking trails situated on 55 acres, and canoeing on Kenoza Lake. On chilly days, curl up in the light-filled Lake Room with a book and a hot toddy.

Originally Appeared on Architectural Digest