1000 Islands Road Trip: Penn Yan to Clayton, Cape Vincent & Sackets Harbor

Many thanks to CM Communications and the 1000 Islands Harbor Hotel for hosting me on my 1000 Islands road trip. The support of businesses and organizations such as these helps me to create useful guides for readers like you. All opinions are my own.

This is part 2 of a road trip through the Finger Lakes and 1000 Islands. If you missed part 1, start here.

1000 Islands Road Trip Day 3 Itinerary: Watkins Glen to Clayton

Along Route 14, on the western lip of Seneca Lake, broad fields tumble down to the shoreline, their flat-topped hills crowned with enormous rolled bales of hay bleaching in the sun. We make it to Earle Estates Meadery, another recommendation of Nancy Koziol’s, just after opening. Predictably, we’re the only customers. We select a pair of blue Adirondack rockers in the shade of the overhang by the front door, and taste four meads, which are lighter and more refreshing than I imagined. Feeling unrushed—something unfamiliar in my daily life—I rock and sip, watching narrow rays of sun creep across my sandaled feet.

Two bottles of mead bundled with our wines from yesterday, we turn off Route 14 onto Leach Road. Here the landscape, dominated by cornfields, is so broad and flat, so unlike the shale-filled hills and spoon-shaped drumlins that characterize the upper Hudson Valley, it looks like you could drive straight into the horizon. We turn again, winding along train tracks and past a large chicken farm, where an enthusiastic rooster heralds our passage.

1000 Islands Road Trip

Where We Stayed
1000 Islands Harbor Hotel

Where We Ate
The Seaway Grille
The Channelside

What We Did & Saw
Penn Yan
Minna Anthony Common Nature Center
Uncle Sam Boat Tours
Singer Castle
Tibbets Point Lighthouse
Westcott Beach State Park
Sackets Harbor Battlefield

Discovering Penn Yan

Penn Yan, on the northern edge of Keuka Lake, lies, like the center of a Venn diagram, over the borders of three different towns. It was settled mostly by transplants from colonial New England and Pennsylvania, hence its name—an abbreviation of Pennsylvania Yankee. A former agricultural trading center and powerhouse dairy producer, it was the site of an early women’s rights convention, headlined by Susan B. Anthony, in 1855.

In the downtown, the sidewalks are undergoing reconstruction and many of the shops are closed—a common refrain during these early days of pandemic reopening. We pause in Keuka Candy Emporium. Lined with pine bins of bag-your-own saltwater taffy, jelly beans, and gummies, it’s one of those irresistible vintage-style shops that makes me pine for candy I haven’t thought about in decades—Sugar Daddies, black licorice fashioned into corncob pipes, brightly colored rock candy on wooden swizzle sticks.

It’s unreasonably hot again, so we shorten our unofficial walking tour of the village’s beautifully preserved historic architecture, and head five miles out of the downtown. On a road mostly populated with wide green fields and splotches of low-growing heather, we find the Spotted Duck Creamery, known for its smooth duck egg–based custard combined with local fruits and herbs.

We order a 4-flavor flight of ice cream mounded in diminutive mason jars, and take it to a shaded picnic table by an enclosure of clucking ducks and chickens. I do a double-take as a peacock, long tail plumes trailing over the grass, weaves in between the tables. And I taste. All four are very good, but the standouts are the Fleur Blue, a sophisticated combination of blueberry and lavender, and the Elderberry Port, which melts on the tongue with the flavor of dark, rich wine.

1000 Islands Road Trip: Exploring Downtown Clayton

Back on the road for our 1000 Islands road trip, we weave through the denser traffic of Geneva, a university city outlined in historic brick architecture, and onto Route 90 East. After nearly two and half hours of compulsively checking the time on Google Maps, we’re spat onto rural Route 12. We finally arrive in Clayton, one of the many upstate towns saddled with the “sleepy” moniker, a nice way of saying “not much happening here.” The street in front of the 1000 Islands Harbor Hotel has been torn up; a woman in a neon yellow vest, frowning against the intense sun, signals us around a pair of backhoes and into a side entrance.

The lobby of the hotel is an oasis on a day like this. A near duplicate of its sister in Watkins Glen, it’s spacious and mercifully cool. We’ve barely gotten through the door of our room when I notice the windows along the back wall. I walk up, let out a low whistle, and allow my bag to slump off my shoulder. “Whoa,” is all I can come up with.

Our room, on the fourth floor, looks out onto a conversation-stopping view of the St. Lawrence River. To our right, there’s Washington Island, its outer edge ringed with homes. To the left, the side-by-side pair of Governor’s Island and Calumet Island. We stand, watching fishing boats and cabin cruisers shush by. It’s easy to see why this region was the playground of the Gilded Age wealthy.

Outside, we walk in an arc along the Riverwalk into downtown Clayton. The streets are under construction here, as well; the town is in the process of upgrading its sewer and electric lines. As in Watkins Glen, most shops close at 5:00 p.m. I cross to the gas station parking lot, where a preteen Amish boy in a black vest and hat staffs a table piled with handmade baskets. He takes a step back as I approach, so I halt, say hello, point, ask a few questions. Traveling at a time like this has made me self-conscious about everything: where I sit or stand, what I touch, how I interact with people I would have engaged without a second thought just six months ago. We’re all navigating new ways of connecting.

1000 Islands Road Trip Day 3 Itinerary: Hiking Wellesley Island

The morning mist is lifting in patches, like a series of veils, revealing traffic on the river: a massive Canadian cargo ship, its hull decked out in bright red and white, a pointy bow rider with a life-jacketed dog panting along its rail, a cabin cruiser that gleams with a fresh coat of white paint.

Thanks to its rural setting and severe winters, the Thousand Islands region is sparsely populated. Wellesley Island is no exception; you can drive for miles without seeing a house or a business. We pass only one restaurant, a low-slung brick building whose sign declares it to be Nut’N Fanci. This is a place, tourists be damned, that prides itself on a no-frills approach to living.

The Minna Anthony Common Nature Center is named for an all-but-forgotten female naturalist, whose pen-and-ink drawings and articles appeared in the Watertown Daily for 25 years. We tuck the $7 parking receipt on our dashboard and set out on the River Trail, which makes a half-loop around the shoreline of Eel Bay, The Narrows, and South Bay.

The initial half mile or so is peaceful, if buggy and short on views. We pass a clearing at the shoreline. It’s littered with driftwood, leaves, and a rotting fish, its open jaw grinning with two rows of needlelike teeth, that’s been dragged out of the water—by human or animal, I’m not sure. Around the mile mark, we pause to take in a dramatic view of wooded hills and moss-covered gray rocks that drop straight into a still, utterly silent bay the color of malachite. 

Exploring the St. Lawrence River

In the car, we take turns swapping our sweat-tacky clothes for dry ones before heading off to our next stop. Alexandria Bay—Alex Bay, in the local parlance—bills itself as the “heart of the 1000 Islands.” It easily could be the region’s commercial heart, with its abundance of businesses and shops—from lumber yards to liquor stores and drugstores, diners with names like Wolfe’s Kountry Kottage, and the rows of shops hawking T-shirts and nautical-themed décor that sandwich James Street, its main drag. With its historic buildings sitting cheek-to-jowl with newer constructions, it has the feeling of a town half in and half out of a time machine.

The heavy smell of oil and exhaust is ever present at the piers, where dozens of boats launch each day. We board Uncle Sam Boat Tours’ Island Wanderer for the Singer Castle Tour. Because it’s operating at reduced capacity, there’s no jockeying for seats. Our guide, Captain Nate, says rain is on the way, and advises us to start on the lower, enclosed deck. No one takes him up on the offer.       

Once seated on the open-air deck above, we’re allowed to remove our masks. The boat motors into the water, Millionaire’s Row—home of many of the Thousand Islands’ Gilded Age mansions—visible off the port side. Off the starboard side, some of the ship-grounding shoals of the St. Lawrence. We could tour the river all day and never see all the islands. I find myself wishing, not for the first time, that I’d completed my scuba certification; the astounding water clarity—up to 50 feet in areas—makes it possible to dive to the dozens of wrecks, some dating back to the 1800s, that rest against the riverbed. Divers have even found intact bottles of booze tossed overboard during Prohibition, when the St. Lawrence was a bootlegging hotbed.

The captain steps inside the cockpit to advise a ship’s mate on avoiding Canadian waters. At the moment, travelers from countries with high covid-19 infection rates, America among them, aren’t allowed over the border. Doing so risks a fine of up to $2,000.

The rain begins to pelt down. Through the gloom, Singer Castle materializes out of the wooded landscape at one edge of Dark Island. We dock and step ashore, getting drenched as we follow behind an animated tour guide, her blond milkmaid braids and bright blue eyes covered by a clear plastic face shield. Singer Castle, she tells us, was created by Frederick Bourne, former president of the Singer Sewing Machine Company, and modeled on the tricked-out castle in Sir Walter Scott’s Woodstock. Either the world’s most sentimental fool or most flamboyant moneybags, Bourne had the castle built in secrecy over the course of four years, then surprised his family with it.

Singer Castle is filled with dark, stone-walled rooms and an assortment of castle clichés, like heavy velvet drapes, secret passageways, and a suit of armor skulking in more than one shadowy corner. Though the sunny, high-ceilinged Breakfast Room and the view from most upper-floor windows are highlights, Singer is, at least for adults, more interesting from the outside.

After the tour, we’re routed through the obligatory gift shop and back onto the Island Wanderer. This tour also stops at Boldt Castle, on Heart Island, one of the great tragic romances of the Gilded Age. Boldt was created by a rags-to-riches German emigre for his young wife, who died just a year before its completion. He never returned to the island.

We reach the landing of Heart Island and its cluster of buildings—made to look old—that house a concession stand, a gift shop, an ATM, and administrative offices. The Disneyfication of the property combines with the stirrings of fatigue and hunger, and I decide not to disembark. In hindsight, I should have booked a separate 30-minute shuttle to Heart Island on a different day. My hunch is that it’s worth it, if you can stomach the commercial stuff.

It’s midday by the time we return to Alexandria Bay, and James Street is clogged with tourists, many mask-free. It’s also hot, with humidity hovering around 60 percent. Uneasy, we hoof it back to the car, and blast the air-conditioner on the ride back to Clayton.

Are There Really 1000 Islands?

Although the archipelago is called the Thousand Islands, there are actually 1,864 documented islands in the region, some with duplicate names, and thousands of shoals. While some look like miniature islands, a land mass must sit above water 365 days a year and support the life of at least one tree in order to be classified as an island. Parts of the river measure more than a mile across, and bay-freezing winter water temperatures can hover at -40 for weeks on end. Six billion dollars in commerce travels up and down the Great Lakes‒St. Lawrence waterway—the longest inland deep-draft navigation system in the world—each year. And yes, Thousand Islands dressing was actually invented here.

1000 Islands Road Trip: An Afternoon in Clayton

There are few tourists in the downtown here. For lunch, we choose The Channelside, which has a spacious, easygoing back deck. We share a salad with fresh local greens, spiced chickpeas, pecans, and goat cheese, and a house-made black bean burger topped with guacamole and a buttery grilled bun. This region doesn’t have the foodie appeal of, say, the Hudson Valley, but The Channelside is a bright spot.

After lunch, we walk around town and admire the handsome Clayton Opera House, the Antique Boat Museum, and DePrinzio’s Kitchen, all of which are closed. Also closed: the Thousand Islands Museum. We cup our hands around our brows and peer through the windows at its timeworn mannequins in period costumes. I poke my head into the Golden Cleat, which stocks a colorful selection of home accessories, and River Rat Cheese, which has a dizzying array of New York State Cheddars and even squeaky cheese curds. 

Although I usually try to pack more into my vacation agenda, somehow this pace, in this place, feels just right. And so after dinner, instead of cramming in one more activity, one more stop, one more something, we pull up a pair of red Adirondack chairs to the fire pit on the hotel patio. I nurse a cocktail and watch the sunset throw Calumet Island’s stone water tower, the last vestige of a tobacco tycoon’s once-grand estate, into specterlike relief.

1000 Islands Day 4 Itinerary: Clayton to Cape Vincent and Sackets Harbor

After a stop at the tiny but friendly Clayton Farmers Market, we aim our GPS toward Cape Vincent, a nearly straight shot to the south on Route 12E. On the outskirts of Clayton the landscape is lush and green, dotted with open meadows and lined on both sides with purple asters and Queen Anne’s lace growing wild and leggy and swaying in the wake of passing cars.

The water views begin a mile or two into Cape Vincent, past a series of trailer parks, small lakeside cottages, a handful of proud old Victorians, and a tiny downtown that we exit almost as soon as we’ve entered. On Route 6, which hugs the shore, the houses become bigger and more spread out.

We pay a visit to the Tibbets Point Lighthouse, built in 1827 at the confluence of Lake Ontario and the St. Lawrence River, and make a circuit around the lighthouse quarters, now a hostel, and the simple brick-and-stucco tower. From there we continue on through a series of increasingly rural towns that look more than a little like the one I live in, past old farmland being reclaimed by time, past houses with rooflines that sag into the tops of windows, past several abandoned barns, sides yawning open, weeds and spindly trees huddled against their weathered exteriors.

Sackets Harbor, even on its outskirts, has a more lived-in quality, even though its population is only about 1,400. We stop at Westcott Beach State Park, coveted by locals for its narrow strip of white-sand beach on Henderson Bay. There may be more seagulls here than people on a Thursday morning. A few groups gather in the water or on towels spread over the sand, their edges tacked down with shoes, coolers, tote bags.

Sackets Harbor’s downtown is compact and has the old-fashioned gentility of the many historic towns along the New England coast—a few blocks of Federal-style and Italianate brick buildings broken by small green spaces. At the end of the street lies Sackets Harbor Battlefield. I’ll admit that I usually find historic battlefields to be a snore. But Sackets Harbor’s, a strategic site during the War of 1812, proves an exception. Its parklike green is abutted on two sides by beautifully preserved Colonial buildings. On the far end, there’s a sweeping view of Black River Bay that prompts Floren to muse that the Brits and Americans had good taste in their choice of fighting locations. 

There are only a handful of other tourists in town. We take our time stopping in the open shops, including Tea Thyme, a tiny gem lined wall to wall with an impressive range of teas and tisanes, plus tea paraphernalia like glazed ceramic cups, Japanese iron teapots, and Moroccan tea glasses. We select four teas to take home, and order a passionfruit bubble tea to go.

Out on the village green, we claim a park bench in the shade of a big oak, and pass the clear plastic cup of sweet, milky tea back and forth, juicy tapioca pearls bursting on our tongues. Three towheaded boys fish from the boardwalk. A woman in an American flag mask walks a tiny, moplike white dog along a grassy clearing. A man with tanned, sinewy arms pulls in the fenders of his boat and pushes away from the dock.

There’s something so easy about the scene that for a while, I let go of my concerns—about work, about the illness, social unrest, and political disputes that have dominated our spring and summer. I shade my eyes with one hand to watch a herring gull coast on the breeze and think, I could get used to this.

If You Have Time…

Take a boat out to Carleton Island, which bears witness to yet another tragic-castle story. Carleton Villa was built by a typewriter mogul, who died of a heart attack on his first night in his new home. The mansion has been empty since 1927. You can’t go in it, but you can walk around it.

Looking for a fixer-upper? A cool $495,000 will buy you this 11-bedroom, 15,000-square-foot home with three waterfronts.

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