Long and Winding Road

Despite our collective vow that we would be going straight home after dinner, I detoured the car unexpectedly into the darkish parking lot of an all-but-abandoned strip mall — a depressing scene where only two businesses remained. The tired chicken wings sports bar groaned in the corner its being “Open,” but we headed instead to the place with the new sign I’d spotted hours earlier, glowing “Crooked Shillelagh” in an eye-grabbing kelly green. There, fussing with the lights outside, the owner greeted us with a weary smile, having accomplished being open “for 17 days and just in time for St. Patrick’s Day, thank God.” Dude seemed grateful for those welcome sales, buoying his recent deep dive into the murky world of new restaurant ventures. Big events make plenty a quiet night less painful.

My friends chose seats at the indoor-outdoor bar, weakly objecting to my nightcap power move by ordering a very un-Irish matching pair of “your best tequila.” I settled in to do what I habitually do and analyzed the menu. Hmm. The “Highland Boar Hock Croquettes” sounded fun, atypical of an Irish pub. The initial angle felt good. Creative, but familiar. The affable owner was happy to offer that his “great chef” sought a reputation for an “elevated” offering. Sounds great, I smiled. And crossed my fingers.

Originally an Arby’s, then the ill-fated Chrissy’s, then the Gavel Grill, this was my first visit. With 723 nearby restaurants to choose from (according to TripAdvisor when I google “Best Restaurants in Naples Florida”), I wondered what percentage ultimately fail. That’s one big-ass plate of competition from which to create distinction. Oof.

Noting sparse decor, four other guests and the ambitious menu —“dismantled” this and “reinvented” that — a sense of familiar dread began to creep, thinking back upon the stupid-big menu that we opened with at Cobblestones so many years ago. I recalled repetitive dope-slap recognitions and a humbling, “What in the hell were we thinking?” 

Just a couple weeks in, Chef Z and I held a fear-and-beer-fueled emergency late-night menu rewrite — having learned quickly the many threats posed by too large a menu in a new restaurant. We laugh now, but waiting 45 minutes for a Reuben and unsold scallops are high-percentage formulas for failure. 

As Cobblestones approaches its 25th anniversary, many memories recall hard lessons learned upon this long and oft-bumpy road — cobblestones indeed. At the Crooked Shillelagh, I considered this bloke’s road map and what directions I might possibly share that could make a difference as he had “finally” set out to realize his and his wife’s dream.

For chuckles, I later polled both past and present Cobblestones staff all too happy to share recollections of historic head-scratchers. Like GM Robin Dupell — a 25-year testimonial — who shares that I failed to heed warnings that being the only one selling “warm bananas Foster” (ice cream sundaes) at the local winter festival was so not a “brilliant idea.” It was not, as evidenced by long lines elsewhere for cheesy fries, hot chili and fried dough while my cold and huddled employees sat idle. Not my brightest moment.

Chef Paul, now with Lowell’s House of Hope, recalls the folly of treating the entire staff to “open bar” before taking limos to see Boston’s Blue Man Group for the annual holiday gathering. That didn’t end so well either. These days, they mostly buy their own drinks during field trips!

“Hey, remember the time, …” recalls Kim (a favorite longtime bartender and manager), we scored and hauled a massive steam-jacketed tilt kettle from a restaurant auction for only $500! I beat my chest “that these things go for, like, $10,000!” That was until the plumber discovered that this particular steam kettle model was missing the remote engine that created, well, the steam. D’oh. She had to console me into accepting the loss and ultimately junking that immense and useless tub of stainless steel.  

I could go on. Twenty-five years creates a formidable list of bonehead moves despite the extraordinary won-loss record and the accomplishments of so many along the way.

All trial and error aside, we have truly enjoyed great fortune in avoiding the unrecoverable mistake. And rather than share tales of woe with new owners — this crazy business is hard — I’d rather simply support their restaurants and share such positive experiences with others. And keep those fingers crossed that every day brings rainbows and pots o’ gold.   

** Fans and friends: On the night of Friday, June 7, Cobblestones will celebrate 25 years with countless folks who have carried us to this rare and memorable milestone. You are welcome to join. Details TBA @ cobblestonesoflowell.com. We’d love to have you.

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