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