Vinny Migliaccio is about to turn 40 but has the spirit of a 20-something guy with big ideas. And this could be the secret to his success. When he was just 26, Migliaccio opened Conundrum Wine Bistro along a stark strip of Route 1 in Freeport. The building, a former flower shop, adjoined what was then his parents’ place of business, the Old World Deli (still there, new owner).

As the son of restaurateurs, Migliaccio knew all too well what he was getting himself into, but perhaps wanted to carry the torch of his family’s legacy. Young, knowledgeable, and passionate about wine and food, Migliaccio had his mind set on opening a place that would fill a gap.

“In my 20s, everywhere in Portland seemed to specialize in just one thing,” he said, recounting the origin of his restaurant’s name. “You could get a cocktail somewhere but not a good glass of wine, or good food but bad drinks. It was a conundrum to me.”

The name is also appropriate for its location. A squat building on Route 1, Conundrum sits below a 25-foot statue of an Indian, known to locals as the BFI, which parents of young children, at least, refer to as the Big Friendly Indian or the Big Freeport Indian.

Brought up to Maine in the ’60s as a roadside attraction, the statue is fit with a feathered headdress. You can’t miss it.

“We were in the middle of nowhere,” Migliaccio said. “But I wanted to create a place where you could go and get a little bit of everything.”


Wine is a big deal at Conundrum – there are over 500 wines by the bottle and 40 wines by the glass – so much so that around April of every year, Migliaccio and his staff choose a new list of 40 wines to be served by the glass from a sampling of 300-400 wines they’ve tested throughout the previous year. But just as Migliaccio didn’t like how Portland restaurants once focused on a single menu item, the wine at Conundrum doesn’t necessarily take front seat.

Migliaccio and his staff encourage a choose-your-own dining adventure vibe, so you won’t feel pressure to order food or even wine. There’s a hearty list of house cocktails, a full bar and 14 beers on tap.

If you’re seated at the curved bar, where rows of wine glasses dangle overhead, there’s a good chance Migliaccio will wait on you directly, or at least act as a support to his attentive staff. He’s proud to offer many, if not all, of his wines at a discounted price because of his long-standing relationships with vendors and wineries. And he might even craft a new cocktail on the spot if you’re not sure what to order.

Migliaccio’s girlfriend, Erin Meuse, has been the chef at Conundrum since the beginning. She has a local, farm-raised burger on the menu, which is superb, in addition to eight other entrees and some great appetizer standbys, such as crab cakes, mussels, and an antipasto plate.

From the outside, Conundrum looks like a tiny restaurant that might hold 50 people, but a covered (and well-heated) patio extends off the back door and can alone accommodate at least 25. Migliaccio says that on a busy night, usually Friday or Saturday, he’ll reach full capacity around 150. For a bistro on Route 1 in Freeport, that’s saying something.

“We keep the prices low and the quality high and it’s pretty simple,” Migliaccio said. “People keep coming back.”

The only conundrum of Conundrum is that there really isn’t one. Everything you could ask for (and more) is pitch-perfect.

Claire Jeffers is a Portland freelance writer.

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