Carefully Crafted Pie

Written By: Luke Osteen | Issue: July 2023 | Photograph By: Susan Renfro

I was fired up to receive this assignment to review Highlands Pizza Place, not only because I’m a sucker for carefully crafted pie but because the place itself has meant so much to me over the decades.

In the 90s, when my young family would come in on a precious night out (how precious? Between my wife and I, we were working a total of seven jobs – I at The Highlander Newspaper/Crossroads Chronicle, and evenings at the world-famous Chandler Inn or Old Edwards Inn; she at Highlands School, piano lessons, and weekend front desk duty and bread baking at Colonial Pines Bed & Breakfast; both of us at our perpetually wobbly Fireside Books, etc.), we’d unwind and take in the comedic exchanges between co-owner (with his wife Sharon) Jerry Taylor and Highlands Mayor John Cleaveland.

(I can’t print most of those back-and-forths, but they were jaw-droppingly hilarious for anyone to overhear. Ask me about them when we cross paths outside of these pages.)

It’s where my Dad and I laughed and shared a Hawaiian pizza and watched the Boston Celtics take the NBA Championship in 2008, both of us unaware that Alzheimer’s was already beginning to shadow his thoughts.

And it’s where I treated the kids on my son Alex’s T-ball team (The John Cleaveland Reality[sic] All-Stars at the conclusion of their astonishing 14-0 First-Place season (even more astonishing, the other teams in the league also took First Place honors).

Owner/Oven Master Nick McCall once gave me extra pepperoni on my takeout because I helped round-up his dogs Elwood and Jake when they escaped.

So you see, I was curious whether the new owners would maintain that warm, neighborhood pizza place atmosphere that had made Highlands Pizza Place into a beloved Community Institution.

And, of course, whether they’d be able to maintain its reputation for quick food produced with care and a healthy dose of pride.

Let’s start with the food – yes, yes, yes, they get pizza and the attendant dishes and sides that keep a local pizzeria hopping.

For me, there’s the Buffalo Chicken Pizza, a new favorite and one more thing to make you proud to be an American. I’ve somehow never considered the palate-pleasing possibilities afforded by placing a sports bar favorite upon what’s become a globe-spanning staple. This simple concoction is ready for its moment on the international menu. Sublime and supreme.

Tricia went for a Meatball Sub – simple and yet surprisingly easy to get wrong. Homemade tender meatballs are simmered in a flavorful tomato sauce, placed in a roll, and topped with cheese. The sandwiches are broiled until golden, and the cheese is bubbly – making for a perfect bite, meaty, saucy, and cheesy, punctuated by that toasted submarine roll.

And since this was a takeout order, I went ahead and got a Hawaiian Pizza, in honor of my Dad and that giddy evening from long ago. Yeah, these new owners get it right, and I reveled in a warm nostalgic glow that carried me back to that golden evening of laughter and cheers and raucous good times.

And about Highlands Pizza Place maintaining that fun atmosphere that’s kept it a cherished Main Street institution since the 1980s?

Still there! I laughed with the patient counterman/oven runner about how I managed to screw up my online order – in my defense, at the time, my 5-year-old tech advisor grandson Griffin was busy watching Puppy Pals at his home in Maryland. It was silly and could have been mildly embarrassing, but to his credit, he never once referred to me as a “Blooming Idiot,” and I left feeling buoyed by this connection.

And on my way out the door, I ran into King Young and his daughter Claire. I hadn’t seen either one since the start of the Pandemic, and it was heaps of fun, just seeing their smiling faces and swapping stories.

In fact, after our meal, I went back and talked to Pam Canary, who owns Highlands Pizza Place with her husband Dan.

“When Dan and I were thinking about buying the place, we knew how important it was to the community to maintain that local, family-run atmosphere,” she said. “When you come in, it’s me or our sons Garrett and Tommy, and our near-son Dane in the kitchen or manning the front. We’ll be slowly changing the décor or adding new things to the menu, but it’s the same local pizza place that Highlanders know and love.”

There it is, Highlands Pizza Place, unchanged, in the best ways, over the last 45 years.