A Canadian Island Where Hip Meets Historic

An island roughly 30 miles across that dangles into Lake Ontario, Prince Edward County packs into a small space stunning beaches and small towns, wineries and a slew of new restaurants. A mixture of the hip and the historic, it offers a rare look at what makes Canada, Canada. Some may confuse it with Prince Edward Island, 800 miles to the east. If you’re looking for Anne of Green Gables, she’s not here.

You can hit many of the county’s attractions by driving or biking across the island on the two-lane Route 33, known as the Loyalist Parkway. Lined with some 40 archaeological sites and 125 listed heritage buildings, the Parkway is itself a kind of historic artifact. Its path follows that of the first permanent pioneer roadway that the Vermonter Asa Danforth laid down, beginning in 1798, to connect Toronto to the west and Kingston to the east.

Roads and land were needed to make way for several waves of refugees, led by British soldiers loyal to George III, who had arrived, weary and penniless, after the American Revolution. To this day the county is demonstrably proud of its Loyalist past.

The Parkway enters the county in the northwest at Carrying Place, a famous portage and meeting spot for native tribes, centuries before Europeans arrived. As the name implies, this is where canoes were lifted and carried between the Bay of Quinte and Lake Ontario. The French explorer Samuel de Champlain stopped here in 1615, and it was also the site of the Gunshot Treaty of 1787, now marked by a small cairn, where the Mississauga relinquished all land west to and including what would later become Toronto. A canal was dug in the 19th century, severing the slim isthmus and turning the county into an island.

Driving south then east on the Parkway one comes to Sandbanks Provincial Park, the largest freshwater barrier beach and dune system in the world. It’s a natural wonder, with wide stretches of white sand, dunes that are five stories high, dappled green and blue water overlaying a gently sloping bottom. The beaches are great for swimming, the dunes for exploring. With the infinite-looking vastness of Lake Ontario before you, you’d be forgiven for thinking you were at the ocean.

While Sandbanks has been the traditional tourist draw, the rest of the county is almost as pretty, carved by long reaches of water and overlaid by green hills, farm stands and small towns with thriving main streets.

Permanent settlement of the area likely took place only with the arrival of the Loyalists — before that it was a place to be traversed or navigated around, on the way to somewhere else. Most who landed were officers and soldiers from disbanded regiments, with their families. They had lost everything. The British rewarded them with land to be cleared, seed and tools. More arrived in the late 1780s, described by Lord Sydney, the British Home Secretary, who was heavily involved in the scheme to resettle the Loyalists in Canada, as “Sufferers under the ruinous and arbitrary Laws and Constitution of the United States.”

The vestiges of the Loyalists are everywhere: the County claims to be home to the second largest collection of Loyalist architecture in North America, after Williamsburg, Va. Locals proudly describe their family trees, headed by ‘United Empire Loyalists,’ though technically ‘UEL’ is only applicable if one’s family served with the British military during the Revolution. More significantly, some historians trace the rise of modern Canada to the Loyalists, their arrival signifying the shift in development of a country that was to be distinct from both the republic to the south and the British Empire overseas.

These days there is migration from a different direction, with the county serving as the terminus of an eastern flyway for Toronto chefs, mixologists, hoteliers, artists and entrepreneurs. Over the past few years the county has been chaotically, bigheartedly reinvented by youthful outsiders leading a hipster cavalry charge of tourism, central to which are some 50 wineries, cideries and breweries.

The surge in coolness can be traced to five years ago when the Drake Devonshire hotel set up in Wellington, a town of 2,000 people close to Sandbanks, whose Main Street forms part of the Parkway. A former iron foundry and inn, the rambling hotel is part of an artsy boutique chain based in Toronto. The Devonshire has 13 guest rooms, a restaurant that practically sits in the lake, a barnlike open-mic space and the Glass Box room with games and morning yoga. Everyone and everything looks good and smells good. Around every corner is art: murals, installations, sculptures.

In May the company opened the Drake Motor Inn a block from the shore. It’s a flawlessly executed, if self-consciously whimsical, take on the vacation motel of 50 years ago: three separate buildings with 12 spacious rooms catering to family stays. On opening weekend an artist flown in from Spain was putting finishing touches on a mural on the outside wall.

Around the corner, on Main Street, is what’s thought to be the oldest house on the island, built by a Daniel Reynolds in 1790. Constructed with thick gray stone, the low-slung residence has been carefully restored to the Loyalist period and remains in private hands. Open to the public is the Wellington Heritage Museum, in a former Quaker Meeting House built in 1885. Wellington also has a thriving farmer’s market, testament to when the county supplied a sizable portion of Canada’s fruits and vegetables. The museum describes the decades when the county’s economy was dominated by some 75 canneries.

Orbiting the Drake are several hip Wellington dining and drinking options. Midtown Brewing occupies a former meatpacking plant with nine of its beers on tap. La Condesa, opened in May, does great Mexican small plates and cocktails like the Zona Rosa, with tequila, grilled pineapple, jalapeño, lime, agave. Across the street is Idle Wild, which also opened this spring: an Asian fusion takeout run by a young couple working with two side-by-side electric ranges, specialties like beef and wild leek dumplings. Two doors down is one of the best bakery cafes in the county, Enid Grace, tiny, warm and full of baking smells, offering brunch and Italian deli sandwiches.

A short detour north of the Parkway, flat landscape gives way to rolling hills around Hillier, with a microclimate hosting the county’s greatest concentration of wineries. Closson Chase’s eye-catching purple barn is one of the oldest, justly renowned for its Chardonnays. A smaller family winery nearby is Broken Stone, with good pinot noirs and Cabernet Francs. Hinterland specializes in sparkling wines.

Returning to the Parkway and continuing east, one comes to the village of Bloomfield, with its handsome, heavyset Victorian houses. Bloomfield was cleared by settlers from Dutchess County, N.Y. Many were Quakers. Running parallel to the Parkway in Bloomfield is the Millennium Trail bike path, recently upgraded to loose gravel. It traverses much of the county, roughly parallel to the Parkway. (Rentals are available at Bloomfield Bicycle.) The trail crosses farms, streams and waterfowl nesting places. The county is also a road-biker’s paradise, and hosts a couple of popular cross-island events each year.

Along the main drag in a former bank is the Bloomfield Public House, open less than a year. The fare is anything but pub-like, with dishes like lamb boudin with braised fennel, or the yellow perch, caught locally.

Continuing east on the Parkway is Picton, a town of 4,000, once a thriving port for timber, grain and rumrunning. Much of the land that makes up the present town was originally granted to the Ferguson clan of four Loyalist officers, a sergeant and six privates, as well as a 10-year-old who had been a member of Rogers’ King’s Rangers, a provincial military unit that fought with the British.

In summertime Teslas arrive to cruise the Picton strip among the locals’ F-150s — it feels like a New England seaside town in July. The Marans is a wonderful new restaurant opening onto the street from the Regent which dates from 1918. The owner and chef, Guerin Sykes, serves dishes like a maki roll that incorporates local pork belly. Mr. Sykes owns a farm from which he sources most of the vegetables he uses. He praises the county’s honor system, which allows chefs to quickly grab ingredients from local farms and farm stands. “A list with prices, a calculator to add up the goodies and a jar for change. What a great way to get the freshest ingredients possible while supporting your local farmers” he said.

The town is also home to Picton’s Books and Company, a rambling shop and cafe with a creaking wood floor and sleepy overfed cat that seem to be standard issue to independent bookstores worldwide.

Surprisingly for an island, it can sometimes be a challenge to make it out on the water in the county. Scott Walcott runs a charter sport fishing operation from the cozy Picton harbor, where ships used to take wheat and barley to upstate New York and as far as England, into the blustery Z-shaped Bay of Quinte, which wraps around the east and north shores of the county. Mr. Walcott says that this particular reach of water is ranked among the top three in North America for trophy walleye, with some fish in excess of 18 pounds.

Tim and Lesley Snyder, the owners of Cabin Fever Kayak, both illustrators, moved to the county a few years ago, “having done that whole soul-destroying Toronto thing,” as Mr. Snyder said. He still moonlights as a syndicated political cartoonist. With watercraft manufactured locally, they launch boats from next to their barn on the Black River, a half-mile upstream from where it enters Lake Ontario. The river’s source is at Milford, where large schooners were once built, a peaceful winding paddle past pretty marshland.

Besides Loyalists, birds also take refuge in the county. The Prince Edward Point Bird Observatory, on the southeastern tip of the island, is a meeting point of several bird flyways, with many of the 130 species in spring coming from Central and South America — the wooded reserve is their first landing and feeding spot after a journey of perhaps 50 miles over Lake Ontario’s open waters. This part of the island, open to visitors year-round, is designated an Important Bird Area as well as a Monarch Butterfly Reserve.

The Parkway leaves Picton and continues up the southern side of the Bay, along which is the June Motel, opened in 2017 by two Toronto émigrés, Sarah Sklash and April Brown. The June targets millennial women. Swatches of pink and sea foam green, a neon-lit lobby and nightly campfires pay homage to motels of the 1960s. Ms. Sklash and Ms. Brown transformed what had been a rundown motel favored by sport fishermen — the new palm-frond wallpaper replaces signs that read “No Gutting Fish in Room.” Unprompted, the friendly receptionist points to the spots in the lobby at which one can take the best Instagram photos.

Just east is Lake on the Mountain. As the name implies it’s a deep circle of water that sits some 200 feet above Lake Ontario, at one of the highest points in the county. Long the subject of native legends, and with no obvious source, its waters are now thought to be continually replenished by underwater fissures in the rocky bottom. It offers spectacular cliffside views of the county and the Bay of Quinte. You’ll also spot the free ferry that runs from Glenora to the mainland. A ferry in one form or another has been plying the same route for more than two centuries. It marks the eastern end of the Loyalist Parkway on the island, picking up again on the mainland on the other side.

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