We crushed this morning's 4.5-hour drive in short order, passing through Sudbury and driving two-thirds of Manitoulin Island, all the way over to the last civilian harbour in Meldrum Bay. This was my first time on Manitoulin Island or up in this area at all - I've never been to Tobermory - and I left very impressed with Manitoulin. I'd love to return and cycletour some of its rolling hills and quiet country roads.

But that's an adventure for another time. Today we were meeting up with five of Isy's cousins, plus her brother, to take a boat out and cover the 20km (12.5mi) journey west to the last Canadian island up here. Situated between the end of Manitoulin Island and America's Drummond Island, that island is Cockburn Island.

Aboard the boat, I got a clue regarding whether the amount of beer I bought was appropriate: apparently her cousins coming from Montreal, every time they stopped for a smoke break it was also a beer break, lol. This sounded a little more exciting than my morning of Isy driving while I continued to work remotely (including working remotely from the picnic table outside the last major grocery store in Espanola).

Anyway, Lake Huron was calm enough and the crossing went smooth. Before long, we were lifting hundreds of pounds of stuff out of the boat, onto the dock, and into a waiting Mazda Ranger and 1990s Suburban that her family keeps on the island. They offered that I could have added to the cargo weight with my bike too, but a flooded breakwall and gravel roads led me to being happy with my decision to leave it behind.

There's always the worry that you're going to end up sitting around in a disorganized fashion when you first arrive somewhere, but I was very happy with how quickly everyone wanted to get moving.

The first stop? Checking out the island church.

Less than a hundred feet away was this abandoned house tucked away by overgrowth between the road and its front door. I instantly made plans to walk down here later and check it out on the sly.

Except that the group was like, "what's the deal with that house?" and started walking right over after leaving the church. Suddenly round back, the whole gang made their way up and into the open backdoor.

This'll work!

It's always funny going into abandoned buildings with people who don't make it a whole personality trait to go into abandoned buildings. With seven people total, we were all bumping into each other as we checked out the various empty rooms, while people also had different appetites for danger in terms of testing the stairs and getting near the floor holes in the kitchen and the attic.

This house was the Staff House, where lumbermen would have stayed back in the day when there were greater lumber operations on the island.

I continued to enjoy the pace of exploration as we went back to the house only to quickly stock up on refreshments, then piled all seven us into the 1990s, 8th-generation Chevy Suburban. The only other time I'd been in one of these bad boys was way way way back, going golfing with Kolowicz and using his Dad's Suburban.

Anyway, all of 45 minutes after we stepped out of the Staff House, we found ourselves atop Cockburn Island at its highest point, McCaig's Hill, 950 feet in elevation.

Not knowing much about the landscape up here, I hadn't even thought to look up any named hills. Therefore I can't say I've actually been atop McCaig's Hill, since I didn't seek out the absolute peak of elevation.

McCaig's Hill and the surrounding area was the location of one of the two island settlements, the village of Scotch Block.

Peering out from the tiny driveway up to McCaig's Hill, the old roadways still occasionally plowed down by hunters, stretched out in every direction and I longed to get back up here using Isy's brother's bike. I was pretty sure that was an apple tree off on the top of the hill too, which really brewed that up that desire to explore these old homesteads in the coming days.

We rumbled further into the island's interior, into areas that were dark due to the road's thick tree canopy. After stopping at some type of abandoned attraction/cabin with a truck marked Uncle Tom's Cabin, we continued on to the old Cockburn Island Indian Reserve No.19 which had ruins of old buildings, a church, cars in the woods, an abandoned boat, etc.

I was kicking myself for not bringing my tripod as the day's last light wasn't allowing me to take anything close to clear pictures. We absolutely had to come back here.

Out in the field was one lone cabin, where without surrounding trees I managed to take a decent picture.

As always, you know that I'm going to provide you with interior shots.

The next morning, Isy, Kingsley and I went for a stroll up to Stone Beach, right outside of the main town/cabin area.

Limestone shelves extend offshore here and it's a great spot to sit atop them as Lake Huron's waves gently come in. Not in October though.

Another thought that occurred to me here was that this was the sole place where Cockburn felt like Michigan's Upper Peninsula. Being only 2.5km from Drummond Island at its closest, I thought Cockburn might satisfy some of my desire to get back to the U.P., but it was more of its own thing than a U.P. clone. Then again, this also has to do with the fact that the only things east of I-75 I've seen in the U.P., are the communities of Sault Ste Marie and St. Ignace right next to the interstate.

Leaving Isy and Kingsley back at the cabin, I went for a stroll around town. It was time for the Cockburn Island history lesson.

After leaving the east coast in ancient times, the Ottawa people settled on lands centered by Manitoulin Island, but definitely also including Cockburn Island. When white people eventually arrived, an 1836 treaty from Upper Canada's governor gave the Ottawa First Nations people "sole use" rights over the Manitoulins (which included Cockburn).

This would last all of 26 years before Upper Canada cancelled that treaty and allowed the Department of Indian Affairs to sell 100-acre parcels to white settlers. The deed to said Cockburn Island land could then be acquired by the settler, if they then built a house at least 18x24 feet and farmed three acres of land over five consecutive years.

Prior to 1879, a commercial fisherman named S.F. Tolsma had built a fishing shed and wharf on the north side of Cockburn, in a protected harbour that would then become known as Tolsma Bay.

Following land surveyors visiting in 1879, lumbermen and homesteaders both showed up in the newly-minted Tolsmaville to build houses and structures, ready to set up their businesses and lives. By 1882, the Township of Cockburn Island was formed, with the boarding houses, mills, and school of Tolsmaville; plus the Scottish settlement of Scotch Block up near McCaig's Hill.

(The Scots had actually built a series of roads to reach Scotch Block, as the steep road up to McCaig's Hill proved problematic for horses in the winter.)

The farmland ended up being great to start, but the rich topsoil was quickly lost and then there was only the sand underneath. This meant that some of the settlers went off lumbering or working in the fishery instead, while they also made money by selling meat and produce to the lumber camps out in the island's bush.

The tax rolls from 1919 to 1922 showed that 500 people lived on Cockburn Island, with an additional 50 First Nations people. There were also the lumberman stationed on the island seasonally.

World War II was the first time many of the Cockburn Island men saw much of the outside world and it led to some of them leaving with their families afterwards. The population didn't totally plummet though, as the lumber operations were small enough not to totally exhaust the lumber stands, so jobs still existed in lumbering for those who wanted them.

In the 1960s, the ferry that used to run from Sault Ste Marie to Owen Sound was cancelled. This left Cockburn Islanders with only one ferry service, and that was the once a week crossing to remote Meldrum Bay on Manitoulin Island.

The general store would close in 1963 and by 1969, when the crossing to Meldrum Bay was also cancelled, almost all of the year-round residents had already left the island, leaving behind a ghost town.

The old owner of the general store wasn't comfortable seeing the island become forgotten though, and the township hired a man to stay year-round to maintain the roads and watch over things, helping people keep up summer properties. The caretaker stayed on Cockburn with his wife from the 1980s to the year 2000, when the current caretaker took over the job and was the island's lone resident for many years.

(Cockburn Island is listed as having a population of zero and it's said that this is due to Stats Canada's policy of rounding down anything below 15. If that's the case though, I'm not sure why Newfoundland's Tilt Cove gets a listed population of five.)

I wasn't gone very long, but it looked like I was already pushing it as I got back and there was lots of commotion.

Cousins were moving around everywhere, getting ready, and loading up three vehicles, with Isy telling me we were off to shoot some guns at the old quarry. Well alrighty!

You already know that your boy hit dang close to the bullseye. I also managed to shoot a shotgun for the first time, something which I always wanted to do after being scared of the kickback at 12 or 13 years of age, during my last opportunity up at my father's hunt camp.

Jamming it right into my shoulder, it wasn't bad at all.

Isy and I were standing back a bit and I quietly told her that I felt like I was in backwoods Kentucky with us shooting guns in a gravel pit, drinking beers, and with the beater Mazda where someone sat in the back on the way over.

Of course she immediately turned and announces this to all her cousins - some of whom I just met for the first time yesterday - that I said this, that hanging with her family in this gravel pit, felt like some Kentucky shit. Ugh, lol.

If the gravel pit felt like Parts Unknown - Kentucky, we were soon back for another dinner that made the trip feel more like No Reservations: Quebec, featuring Isy's chef cousin and the decadence of each meal. Normal cheese wasn't good enough, it needed to be curds. Normal deli meat wasn't good enough, it needed to be some artisinal meat from a local butcher. Everything was so rich and delicious.

Following that it was time for a nighttime poker game, and after all the points I scored with the Kentucky comment, I decided to break out my Ben Affleck Bruins jacket that I brought thinking it would be funny to wear around all of Isy's fanatic Habs fan cousins.

I didn't even make it back to the poker cabin before running into cousin Nicolas on the way over and he didn't find it funny at all. His reaction was almost uncomfortable, where I decided to avoid the rest of the cousins and return the ol' Bruins jacket to my duffle bag.

Anyway, after getting eliminated from the poker game in a spot where I had my money in good, it wasn't a late night and I was ready for more exploration tomorrow.

Continue to Part 3...