Pinelands Resort and the End of Summer

I’m pretty sure only the luckiest kids ever got to spend an entire summer working in Muskoka, Ontario. Because working at a lakeside resort as a student was the best summer job ever. And I got to do it.

The passing of Labour Day weekend in September always brings back memories of the end of summers working at Pinelands Resort in Muskoka. It was the first time I truly learned that “time flies when you’re having fun”. With two summers under my belt working as a waiter at this lakeside resort near Port Carling, I was left struck that the eternity that was once the beginning of summer (traditionally the May long weekend) came to such a quick end.


Mid-afternoon meant lunch for staff. Probably just left overs from last evening’s dinner for the guests.

How did a kid from Scarborough end up serving plates of Prime Rib at a 100-year old resort on Lake Joseph? During the winter of 1994, as a U of T student, I was pondering my summer job prospects. While in school I worked weekends in a sporting goods store, selling ski and hockey equipment. A co-worker, his name was Brent, told me about his job the previous summer working as a waiter at Pinelands. Getting paid to spend the summer in Muskoka? I was sold.

The next day (this was in January) I was on the phone to the manager of the hotel, hoping I correctly wrote the number Brent gave me, and trying to decipher my own pencil writing on a crumpled skate-sharpening invoice. I was thrilled when the hotel owner, Bruce, phoned me in a couple weeks to invite me to an interview in Toronto. Seems most of the staff were from Toronto, and by February I was standing in a hallway of the 400/401 Ramada Inn, waiting with 100 other university students for my job interview.

I was offered the job a couple weeks later, and told to report for duty at Pinelands Resort on Thursday, May 19th. “It’s on the north side of Highway 118, just east of Glen Orchard”, Bruce explained. “You’ll see the sign”, he assured.



The first day of work was really just an orientation session. It was about 5pm, and the first signs of the sun setting over Lake Joseph were emerging. Standing in the “Fairfield Room”, overlooking the lake, was the first batch of about 25 staff to arrive, I think about 40 of us ran the resort each summer – waiters, cooks, housekeeping and recreation staff.

After getting a pep talk from the managers and a tour of the expansive resort, which included a main lodge, restaurant and several other cottage-style rooms on several acres, we were ready to start our summer. I distinctly remember thinking it would last forever. How could it not? It was May 19th. Even the August Simcoe long weekend seemed ages away.


This was on a rare day-off. I’m the guy in the BALA shirt.

And only a few of us worked full-time there until business really picked up in late-June. The first few weeks had me helping out with painting, cleaning, digging, raking, and whatever else was needed to make the resort presentable after a harsh winter. This was my first lesson in hospitality. Nice hotels just don’t look that way. It takes endless hard labour to make a place shine.

And after weeks and months of serving tables, making new friends, going to parties with staff from other resorts, hanging out in Port Carling and trying to save money from that $6.75/hour wage, the summer came to a sudden end. By Labour Day it was all over. And nothing shocks you back to reality than driving along the long, white pine-shaded gravel driveway of Pinelands resort one last time, knowing that you’re back in university the next day, studying, going to classes and worrying about exams.

Pinelands is gone now (see also Clevelands House which still survives). The old lodge was demolished around 2006 and a time share community was built over top. And I wonder what that last crew of staff thought on that Labour Day afternoon, driving away as their summer ended too, perhaps knowing they were the last to ever experience a Pinelands Summer. After all, those summers were the best.


Pinelands Resort in all its summer glory, sitting on the south shore of Cox Bay, Lake Joseph, Muskoka, circa 1994

Mike Chopowick – September 5, 2016


10 thoughts on “Pinelands Resort and the End of Summer

  1. My family started going to Pinelands in the earlie 60s. Went went with other families I believe we were known as the Yanks back then. We would go up twice a year once in a while 3.
    We were the gang from Niagara Falls, New York. Some fished, most water ski, some just for swimming and sunbathing. I think the biggest group from what I can recall was 64 people children included. We had the lodge really full the cottages, seemed we had almost the whole place. What a great time we all had. Back then the waitresses lodging was called Casaloma. We use to ski by the Glen Home and Elgin house, waving and some of our better skiers putting on a few great moves. We would gas up in Port Carling. Names – Kromers, Antonacci, Leggetts, Redding’s, Murphy’s, Smith’s, also friends.

  2. My Great Great Grandfather started Pinelands lodge with I believe two other gentlemen.Nice to hear stories of Pinelands. Cheers!

  3. Pingback: Clevelands House | The Little Things

  4. Spent a couple weeks there in the early 80s with my family. Learned how to water ski from Bruce and his brother Barry who were in charge of entertaining the kids and excursions. Remember making ‘life-long” friends each summer and discovering some good Canadian rock music! Vivid memories and great times! Thanks Mike.

    North Tonawanda, NY

  5. Who knew that playing every version of trivial pursuit in the game room with my dad would become the most cherished memories from my youth! The place also gave birth to my fondness of very large spiders when I encountered my first in our room, one about the size of my seven-year old hand.

    Great read. Thanks for sharing your memories!

  6. My readers should note: The “palace cabin” mentioned in Gina’s comment was an old, stuffy camping trailer, up on a hill hidden behind some trees. It took on a more palatial look and feel after consuming several bottles of Labatt 50 beer.

  7. I spent a couple summer vacations here with my family. Fishing, swimming, water skiing, horseback riding and canoeing to an Island where we jumped off cliffs into the water. talent shows, and hanging out with staff at the palace cabin out back and walking to the sand dune parties. The Reville ? Family were wonderful hosts as were the staff. I very much wish I would have gotten back there before it changed hands. This place will always be a fond place in my memories.

  8. This was a really neat read. My great great grandparents started pinelands. I was lucky enough to spend a summer there when I was ten. I’m sad it’s gone now.

  9. My best memories as a child were spent here…my father has since past but remember spending my childhood vacations’s taken me a when to find this gem. .apparently it’s changed drastically but I’m making a point of coming here soon…has been my only wish in my life…before I pass I want my Muskoka chair and loons in the mist

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