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Take a Road Trip Through CT's Northwest Corner to Millerton, New York

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The historic, 11-room boutique Millerton Inn in Millerton, New York.

Story and photos by James Gribbon

The first move I make on the day of the trip is to cancel it. A full day after they began, April showers are still blocking the sun and drenching the roads — a bad start for a photo-intensive road trip story. I call the inn at my destination in Millerton, New York, just across the border from Connecticut’s northwest corner, and leave a message telling them I’d need to reschedule. Twelve hours, 75 miles, and a significant change of heart later, I am sleeping in one of their beds. The best road trips make for eventful days.

Put the words “road trip” together, say them out loud, and they open a small door into the American soul. Maybe it’s a memory from college, a passage from Kerouac, a ride to beaches, a lake, the mountains, and the people we were with. For a lot of us, so often tidally locked in the flow of traffic, a car trip is a grind to be endured, like it or not. In a state where the roads are often not great, and highway travel typically more of a slow ooze than a fast flow, can there ever be a little adventure, even joy to be found in the journey itself? I thought I could prove so. 

Millerton was a dot and a name on a map, a capillary knot of street squiggles across the dotted line from Lime Rock Park every time I went up to the track. But I’d never hitched up my figurative britches and stepped across. I knew most of the byways to get up there by memory: fun, rolling, bucolic roads, with more than a few excellent stops to sightsee, eat and explore. The end point, the goal of the trip, is the mysterious part. A quick online search of the village turns up The Millerton Inn: an attractive, 1860s-era manse that underwent a restoration into an 11-room boutique hotel in 2015. Looking outside, I glower at the clouds, send unfriendly mind-beams their way, and pick up the phone to reverse my cancellation. Let’s hit the road. 

As just about everyone reading this magazine knows, I-95 does not produce feelings of relaxation and contentment in its travelers. We thus begin our trip heading directly away from the coastal highway, hand raised over our shoulder in farewell, or whatever other gesture is inspired by past experiences, and hit the on-ramp to the less heavily trafficked Route 8 north. Wherever you pick up the highway, 8 seems to let you know you’re actually getting somewhere. The tightly spaced towns of the lower Naugatuck River Valley flick past, and before long the sense of unbroken city life in southern Connecticut begins to fade away. Hills rise up on either side like shoulders as Route 8 flows along with the rushing braids of the river. The last major city you’ll see on the trip is Waterbury, and that’s only in passing as you follow the river through the Mattatuck State Forest to exit 38 at Reynolds Bridge.

Getting there is half the fun

The first waypoint reached, continue on state route 109 toward the day’s first destination. Route 109 exits the post-industrial valley and heads directly into the woods and waters of Black Rock State Park in Watertown. Tiny creeks and cascades mark your trip in reverse as they run downhill and you move up to the earthworks and sheeting spillway of the dam at Morris Reservoir. Switch to 63 north in East Morris, and buzz along the ridge with agricultural scenery on either side. White Flower Farm is an explosion of color in Morris, and just a few miles up 63/South Pains Road in Litchfield is the internationally award-winning dairy at Arethusa Farm. Open barn tours are available on summer Saturdays, but take a left onto Webster and Bissel roads into the center of Bantam, and Arethusa options include the farm store — with incredible ice cream, plus gold medal-winning cheeses — fine dining at Arethusa al tavolo, and smaller sandwiches, coffee, and small pieces of art in the form or baked goods at Arethusa a Mano.

I stop for lunch on the gorgeous Colonial-era green in Litchfield as bright sunlight begins to scatter the clouds, and head straight for a favorite spot, At the Corner. Situated, yes, at the corner of Route 63 and West Street, At the Corner is across from the Litchfield Historical Society, and roughly between the Litchfield Law School (the first in the U.S.), and the home of Revolutionary War hero Benjamin Tallmadge. This is a gastropub with a true focus on both halves of the word. The tap list consistently includes stellar in-state choices from around Connecticut (look for Fox Farm and Kent Falls breweries if you want to stick with the farm-to-table vibe), and the food is a plane of existence above a simple lunch at the pub. I have a special of braised and shredded chuck roast with grilled poblanos and chipotle cheddar cheese over corn arepas, but I’d also like to draw your eye to the year-round Local burger, with Blue Moon Farm (Harwinton) grass-fed beef and Arethusa Farm blue cheese. Drivers experiencing a bout of temporary abstinence — town resident Lyman Beecher, father of Catherine, and Harriet Beecher Stowe, would approve — can get pint cans to go for later, and Litchfield Distillery can be found halfway between Litchfield and Bantam on Route 202.

Now halfway there, the best is on the way as we leave downtown past early American mansions on Route 63/North Street, where you’re met with gentle curves and wide country roads past Sunset Meadow Vineyards, and a straight blast to the roundabout at the junction of Route 4 in Goshen. Swing a quick left to the west on 4 to Sharon, and the real fun gets started somewhere just past Tyler Lake as the road starts to kink on its way uphill. Sinuous curves rise and fall away as one motors along the flanks of Mohawk Mountain State Park and the forest seems to bunch up and unwind before you. Check your zeal on the way down the mountain, and your reward is a trip through the famous covered bridge in West Cornwall, over the trout-filled races of the upper Housatonic River.

The river leads Route 7 north deeper into the woods of the Litchfield Hills and the way to Millerton. Follow 7 as it traces the valley up to a split at White Hollow Farm and a left on Route 112 to Lime Rock Park. The oldest sports car track in America, and a true park set into grassy hills, it’s a stop for another day. Minutes later, look for a sharp right onto Wells Hill Road (halfway up, a bowl-shaped marker lets you know you’re on the right path) and then a left on Route 44 in aptly named Lakeville on the, uh, frustratingly named Wononskopomuc Lake. Follow 44, and you’ve arrived in Millerton. It’s a short trip for those in western Connecticut, depending on stops and the weight of the driver’s right foot, but it can also be a much needed reminder: leave the interstates and street lights behind, and there’s still real pleasure to be had in the journey. 

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Shops along Main Street in Millerton, New York.

What to do around Millerton

The village of Millerton started as an ironworks and railroad depot in the middle of the 19th century along what’s now the Metro-North Harlem Line, and the vestiges of its busy, steam-era past are scattered around the short dogleg left of Millerton’s charming Main Street. Everything is walkable in town, from the Harlem Valley Rail Trail across the street from the old station square buildings — now inhabited by a few businesses, including a bursting florist — to the tea room which serves as home base for the master tea blenders of Harney & Sons. I have a hot cup of their organic green tea with citrus and ginkgo as part of an enjoyable breakfast at the deceptively throwback-looking Oakhurst Diner, and like it so much I get a bottle of Harney & Sons iced black tea (also excellent) to go. Stimulant fans who have graduated to the harder stuff can get their fix just up the street at Irving Farm Coffee Roasters, next to Phil Terni’s general store.

Record shop? Book store? Bakery? Wines? They’re all here, often right next door to one another. Directly across from the Millerton Inn is Manna Dew farm-to-table restaurant, where diners are enjoying a clear, warm evening on the sidewalk patio, and 52 Main, a tapas-style bar which is definitely worth your time if you a) want a quick bite and a drink any time, or b) want to have a little of the loud kind of fun later on while live music plays and the older crowd has long since flipped the light switch on their night.

Along with a room reservation, I have dinner plans at the Millerton Inn, where father Peter and daughter Eleni Stefanopoulos have created a Mediterranean-influenced menu in a Victorian setting. Lovely as its appointments are, I eschew a table for one in the restaurant and take a comfortable seat in the more modern taproom, where the same dinner menu is also available. A firm believer that one must never eat on an empty stomach, I start with a sweet, spicy mezcal cocktail, and order the Airline Brick Chicken — a cut that includes a boneless breast and the wing’s drumette — served with roasted tomatoes and Cretan olives on a bed of confit fennel, alongside grilled asparagus. Both the dinner, and the service from start to finish, are excellent. 

Stay in Room 2 at the inn, and a thick, soft, four-poster bed takes up only a bit of the ample space, which retains its marble fireplace (now gas and remote operated), and opens out to a personal balcony with outdoor furniture and a view down Main Street to the hills beyond. The experience is like being a guest in a friend’s home, and my hand is slow to leave the key at the front desk the next morning.

Making a whiskey run

Before I leave, though, I take a side quest which proves to be one of the trip’s highlights, seeking Hillrock Estate Distillery in nearby Ancram. Hillrock is new, but the farmhouse dates back to 1806, and its land has always been in the business of growing grain. They are a true estate whiskey producer, with the grain grown, malted, distilled and bottled on site. Follow Route 44/Main Street through Millerton and head toward to junction of Route 199. From there the road rises through emerald rhomboids of working farmland. The route swells and bends with the topography, eliciting several “Woo-OOO!”s from me, as well as a few staccato curses as I dodge potholes and aloof, some would say downright arrogant, pheasants.

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Hillrock Estate Distillery in Ancram, New York, uses the rare solera method to barrel-age its whiskey.

Hillrock is just off Pooles Hill Road, with the stately farmhouse uphill from the distillery and tasting room. Owners Jeffrey Baker and Kathy Franklin brought in master distiller Dave Pickerell from Maker’s Mark to design the recipes and operation, and have 90 acres on site, plus another 700 in production, growing barley, rye and corn. My tour guide, Anatol, emphasizes the terroir aspects of estate growing. The farm, he says, gives the grains cinnamon and clove aspects, no matter what type is grown in the fields. Barrel aging is the key to all whiskey, and Hillrock uses a rare solera method with their bourbon, wherein a portion of each previous batch — going back to the first ever — is added to the next, keeping a “family line” of flavors and compounds in each bottle, somewhat like a balsamic vinegar, or gueuze lambic. 

A taste of the bourbon starts with a bit of heat from the nose, but a smooth start on the tongue, with vanilla from the barrels, and subtle hints of the cinnamon from the Ancram terroir. It’s apparent the Solera Bourbon is absolutely superior even before the hot finish burns its way down your throat, with a touch of sherry in the aftertaste.

Most of the country’s rye was produced in this region until the 20th century, and rye was what New York drank, giving us the Manhattan cocktail, among other gifts. Hillrock’s rye is just that: 100 percent estate-grown rye, switched out halfway through the aging process into more deeply charred barrels to reduce the tannin content and bring out the natural spices in the grain. It’s then finished in madeira and other wine casks for triple-barrel versions. The Double Cask Rye I try pours the deep, dark amber of maple syrup under a sweet, pungent nose. The depth of grain in a sip is reminiscent of molasses bread, with notes of clove and allspice. Easily the finest rye I’ve had, it is amazingly about half the price of the other bottles on sale at Hillrock — $50, compared to an average of $105.

Next to the all-copper distillery, available to see as part of the tour, the malting process may be the most memorable sight on location. Grain is brought to a malting floor above the distillery, then hand wet and raked until properly malted, making it one of the few distillers left in the world to use this process. Some of the grain is then taken to a kiln where it is smoked over imported Speyside peat, to be transformed into Hillrock’s Single Malt. This is then aged first in bourbon barrels before a secondary rest in Pedro Jiménez or Oloroso sherry barrels. The result is a single malt which retains a fresh, bright character. The peating is prominent, but it’s by no means a smoke bomb, with rich caramel undertones giving the whiskey form and substance.

A vacation is all about getting away: escaping the drudgery of the daily drive on the same roads, being free to have new experiences, and looking around a new environment which may just impart a new perspective on the area we call home. Follow this route, or blaze your own trail — just know that yes: there’s still some adventure left in the journey.


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This article appeared in the July 2019 issue of Connecticut Magazine. You can subscribe here, or find the current issue on sale hereSign up for our newsletter to get the latest and greatest content from Connecticut Magazine delivered right to your inbox. Got a question or comment? Email editor@connecticutmag.com, or contact us on Facebook @connecticutmagazine or Twitter @connecticutmag.