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New York Route 22 offers quaint drive through fall foliage

Fall colors are a blast in the

Fall colors are a blast in the upstate hamlet of Hillsdale. Credit: Alamy Stock Photo / Mark Dyball

It’s fall foliage time again. The back roads of the Northeast are calling, and few thoroughfares are better for a day trip or weekend getaway than New York’s Route 22.

The longest north-south road in the state (and the third longest overall), this 337-mile two-lane blacktop winds its way from Westchester County and ends not far from the Canadian border. Running through New York’s extreme eastern flank, Route 22 will take you deep into upstate and the eastern portion of the Hudson River valley, through pretty towns, wooded stretches and farm country. You’ll see plenty of fall color along the way, with nary a strip mall in sight.

The road skirts the borders of three New England states — Connecticut, Massachusetts and Vermont — giving you even more options as you plan a trip. You can always branch off and do the Berkshires. Or, if you’re feeling really ambitious, Route 22 will put you in striking distance of the Adirondacks and the shores of Lake Champlain, where you might camp lakeside.


I start at the Cross-Westchester Expressway to get onto Route 22 in White Plains. It would pretty much be a straight shot, but instead I opted for a day trip, and didn’t have to wait long for some surprisingly breathtaking scenery: the Kensico Reservoir, just north of White Plains, almost startling in its unexpected beauty. You’ll hardly think you’re driving through a densely populated suburb. Here, the road bisects this woodland-rimmed body of water — it’s filled with water from the Catskills and stocked with brown trout. You can pretend you’re the star of your very own car commercial as you press north along a winding road.

If you’re feeling flush, you could call it day and head for the nearby Bedford Post Inn, an eight-room luxury hotel owned by Richard Gere. It’s a few miles east of Route 22. There are two restaurants at the hotel — The Barn and Campagna — both under the direction of James Beard award-winning, Michelin-starred chef Michael White, but for an excellent weekend brunch, visit the more casual Barn. You can start off with a “pick me up” juice (beets, carrots and ginger), and satisfy your sweet tooth with a Dutch pancake, or fill your savory craving with baked eggs in tomato sauce (


The route’s small towns are the highlight of this trip. In Katonah, a hamlet of Bedford, you can take in some art at the small but well-regarded Katonah Museum of Art ( For the historically inclined, there’s beautiful John Jay Homestead. An author of the Federalist Papers and the first chief justice of the Supreme Court, Jay doesn’t quite have the renown of Alexander Hamilton, his fellow New York Founding Father, but he deserves a place in the pantheon of great American political figures. This 62-acre site offers formal gardens, lush meadows, old farm buildings, as well as Jay’s house, which dates back to the 18th century (

At the northern end of Westchester, around the towns of Purdys and North Salem, the landscape gradually turns more rural. September is prime apple picking season, so for a family outing, head to the Harvest Moon Farm and Orchard ( The season begins Sept. 10. After you stock up on apples and other fall treats, head to the Red Rooster Drive-In for burgers and shakes. Located on Route 22 in Brewster, it’s generally crowded and cash-only, but worth the wait. The French fries are excellent, as was the black-and-white milkshake that I slurped down.


The Appalachian Trail begins its turn to New England as it winds through eastern Dutchess County near Pawling. You can hike a bit of the trail, or take one of several side trails in the Pawling Nature Reserve, which offer views of the Harlem Valley (

For a bite near Pawling and environs, the acclaimed Big W’s Roadside Bar-B-Q serves up seriously tasty slow-smoked spareribs and other specialties in Wingdale. It’s a nice spot for a crisp fall afternoon, especially if you spent the morning hiking.

Definitely worth a stop is the quaint town of Millerton, also in Dutchess County, set amid rolling hills and horse farms running into Connecticut. Stroll through the main shopping district for some upscale bohemian chic. Visit the fine independent bookstore Oblong Books and Music ( and stop for coffee at Irving Farm Coffee Roasters. Do some antiquing at Honey Bee, and be sure to visit the old-fashioned sporting goods store, Terni’s. By this point you’ve likely worked up an appetite, so stop in at 52 Main for tapas, or try the retro boxcar diner, Oakhurst. All of these stops are located on one charming stretch of Millerton’s Main Street.


Millerton would be a fitting end to your day, but if you continue north, you enter the farm country of Columbia County, which is bordered by the Taconic Mountains. It’s a beautiful range in its own right, even if the nearby Berkshires get all the attention. Keep your eyes peeled for one of many numerous farm stands on and off Route 22. As you pass Copake, Taconic State Park is just to the east. The town takes its name from the nearby lake and the country here is some of the most beautiful on Route 22. The farms give off a bucolic vibe, and the wilderness beckons in the distance eastward.

Near Copake is another small hamlet, Hillsdale. The Hillsdale General Store ( is fun to poke around if cookware is your thing. And indulge your sweet tooth at Village Scoop, which also offers locally sourced bread, cheese, granola, and yogurt from Columbia County.

I could have kept driving — the lure of Lake Champlain was strong. But the tug of family and a busy week was stronger. I didn’t feel cheated. And neither will you.

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