Connecticut: Walking Inn to Inn in Fairfield County

aahusb leavesLocation: Fairfield County, CT., and a little bit of NY

Type: Village, countryside

Distance: Just under 30 miles, (or 20 miles if you take the train partway)

Duration: Three Days, two nights

Difficulty: Easy to moderate (second day was 14 miles).

Highlights: Small towns, historic inns, great food and drink.

It's easy to travel inn to inn along Fairfield County's trails and mainstreets. This walk, from the Silvermine Tavern in Norwalk, to Ridgefield's Stonehenge Inn crosses into New York state for a stretch. Though it was late fall when Anne Lutz Fernandez (author of the recently published book Carjacked, The Culture of the Automobile and its Effect on our Lives) trekked the twenty-something miles from inn to inn and back, this is an ideal walk for (almost) any season. And  it's a cinch to hop on the train if you only want to walk in one direction.

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Fairfield County, where I live and work, is a little jigsaw puzzle of Connecticut suburbs clustered along the commuter rail line  out of New York.  Like residents of most places that are wonderful to visit, my husband and I rarely experience what it offers to tourists.  So it felt oddly exotic one Friday evening in October to be locking our door, turning our packed backs, and heading out of our neighborhood toward a historic local inn.

The Silvermine Tavern in Norwalk is a well-known county landmark and an area institution:  mention it to a local and you’ll hear tales of their brother’s wedding or boss’s retirement party.  The antique-filled white-porched inn, one of a collection of buildings dating back to the 17th century, sits at a crossroads in a historic neighborhood on the Silvermine River.  It took us fewer than four miles to reap the reward of a night’s sleep in one its lace-canopied beds.

In the morning, we sat in front of a fire in the dining room overlooking the river and chatted with innkeeper Frank Whitman while we partook in a motivational, if not doctor-recommended, breakfast of hot glazed cinnamon rolls and coffee.  Our wildly divergent answers to his question of how long we expected it to take to get to our next inn likely alarmed him; still, Frank appeared cheerful as he waved us neophytes off. County map and Google Transit printouts in hand, we headed up along the river, busy with duck traffic, into New Canaan. 

The Silvermine area is wooded and adorned with charming homes; there can be no better time of year to walk here.  With Halloween a week away, pumpkin-topped stone walls and centuries-old graveyards slowed our progress, creating too many photo ops.  At home, only a few miles nearer to Long Island Sound, the trees were just turning, but as we travelled north, we enjoyed the peak New England foliage of vintage postcards.

Farther into New Canaan, the startlingly magnificent, now multimillion-dollar homes diverted our gaze from nature’s splendor, and for a few miles, we stoked our rising real estate lust with a mock house hunt, abandoning any Transcendentalist spirit that had taken hold along the river.  And while the scenery was bucolic—we passed a creek where frogs hid among fallen leaves, an orchard where apple trees hung their fruit into the street, and a field where donkeys peered out at us from a barn—a symphony of leaf blowers working acres of yards reminded us we were still in the suburbs.  (I know: Connecticut donkeys?)

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We made it through New Canaan without passing out from either envy or hunger, sitting to eat a snack on the stone wall of a for-sale mansion we decided was just a tad too big for us anyway.  Restored, we headed off again and were soon stepping across the border into a little corner of New York State, where the paved road turned abruptly to dirt and there was a sense of being thrust suddenly deeper into country.  Here it was quieter; we walked several miles without being passed by a vehicle.

Crossing back into Connecticut, we traversed a pretty bit of Wilton, where we stopped near an equestrian center to chat with a teenager tending her horse, who had an explanation for the donkeys (horse people own them because they help keep horses, which are pack animals, calm) and photographed a series of pastel-box vistas.  We encountered our first car traffic on Main Street, but the reappearance of a sidewalk—we’d left the last behind in Norwalk—allowed us to safely gawk at the collection of Colonial, Revival, and Victorian beauties that line the approach to Ridgefield’s downtown.  We devoured a well-earned late lunch in the village center, listed, as are parts of Silvermine, on the National Register of Historic Places, then forged on to Stonehenge Inn, though our feet would have preferred the nearer-to-downtown West Lane Inn.  (Honey, please know that I didn’t know this other, closer inn existed at the time.  Really.  And why would I even bring this up now?)

The Stonehenge, to which we had been lured by its famed restaurant, was a sight so welcome to our tired selves that it didn’t need to be as remarkably lovely as it is, cozied up next to a placid lake that reflects back its beauty.  After making sure the woman checking us in understood that we had walked 14 miles to get there—yes, all the way, from Norwalk, on foot, that’s right, yes we did—we fell into our room and into sleep, waking to walk down one flight to dinner, where we were treated to very modern cuisine of salmon tartare and seared Ahi tuna that belied the traditional décor.

On the walk back—okay, so we didn’t walk the whole way back. A few miles into our trek home, we came upon the Branchville station, saw that the next Metro-North train was scheduled to arrive in exactly one minute, and jumped on it, feeling a bit guilty and a heap relieved.  Fifteen minutes later, we got off about an hour’s walk from home, where a hungry cat complained about our absence, a pair of couches said they were glad to have us back, and by dinner, we were planning our next weekend walk.


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Tags: 3 days | Bed Breakfast | connecticut | east coast | food | inn | inn2inn | moderate | new england | northeast | self guided | upscale | village | walking

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