walk into Conundrum Wine Bistro on a Friday night and the place is buzzing. A couple sits on high-backed bar stools pulled up to a tall table, drinking wine and sharing a cheese plate. Every seat at the bar is filled; some patrons are having a drink and chatting, while others tuck into generously portioned entrees like veal parmesan or a curried shrimp quesadilla. On the enclosed back deck, heated by gas fireplaces in the colder months, a large party is settled at the teak table in the center of the room, while in the front room couples and parties of four and five eat their meals at cozy tables set against dark blue walls.

There's a lively hum in the air as owner Vince Migliaccio bustles about, leading diners to their seats, pointing a server to a table that needs clearing, stopping at the bar to make sure the bartender is well stocked. Migliaccio, 32, is warm and energetic, greeting a regular, then checking in with the small group of patrons huddled by the door as they wait for a table. The overall effect is comfortable and low-key; while you'll be well taken care of, the restaurant seems to promise, you won't be fussed over or put on the spot.

Migliaccio is convinced that atmosphere is why Conundrum has become a haven for locals and the handful of tourists who've stopped staring at Freeport's forty-foot-tall wooden Indian, a landmark for generations of travelers on Route 1, long enough to realize there's a restaurant tucked behind it. Just three miles south of downtown Freeport's outlets, the restaurant offers diners choices ranging from a burger and a pint of locally brewed beer to a mousse de foie de canard with truffles and a $1,000 bottle of Ch?teau Margaux.

Migliaccio's goal in opening Conundrum five years ago, he says, was to create a place where diners could "fill your belly, get a good drink, and leave with money in your pocket." In some ways, he designed the restaurant to be all things to all people; the twenty-three-page menu begins with two pages of specialty martinis, ranging from the Green Demon (Ketel One Citroen, Midori, and pineapple juice) to the White Satin Mocha (espresso, Godiva white chocolate liqueur, and Absolut Vanilla), then moves on to an extensive list of vodkas, tequilas, gins, whiskeys, and beers before arriving at the eleven-page wine list, which includes sixty selections available by the glass. Finally, on page sixteen, you get to the food.

Here, the array of choices is less mind-boggling, although there are still several categories of items from which to select. Much of the menu bears an Italian influence, a nod to Migliaccio's heritage, in the form of antipasto, a fontina panini, or rich ravioli stuffed with sweet butternut squash and topped with a sage, butter, and cream sauce. But there are also more unusual options, such as the three choices of paté (pork, goose, and the aforementioned duck). Only one entrée, a twelve ounce New York sirloin, tops $16, with most meals in the $10-$13 range.

The abundance of food and drink possibilities springs from what Migliaccio freely admits is his unwillingness to make decisions. The wine closet, a well-lit locked room to the side of the dining room, is testament to his excess; every slot in the wooden racks is filled, and cardboard boxes full of bottles are stacked against the glass walls. "I can't make a five- or ten- bottle wine list and be happy," he says. "There are just too many good options. Do I need 550 good bottles? No, but the one time you come in and want a 2000 Bordeaux, I've got it."

conundrum itself was created out of a similar spirit of playful perversity. Initially, Migliaccio didn't want to get into the restaurant business. His parents had been in the business for years, running restaurants and delis from Rhode Island to Maine (including the much-loved Portland Wine & Cheese shop), and Vince saw the hours they put in, the physical labor, the difficulty of turning a profit. So after graduating in 1992 from Cheverus High School in Portland, he went off to college to study psychology and biology, then came back home to take a job as a psychiatric technician at Spring Harbor Hospital.

He enjoyed the work but he felt the lure of the restaurant industry pulling him back to Freeport, where his parents ran the Old World Gourmet Deli. Vincent and Marge Migliaccio owned the building tucked behind the Indian, and while their deli was doing fine, they had trouble keeping a tenant in the other half of the space.

Young Vince's solution? He should open a restaurant there. His parents disagreed, reminding him of everything he already knew about the difficulties he would face. But Vince dug in his heels, and eventually convinced his parents that his plan was a solid one. "If it's in your blood, it's in your blood," he says with a shrug.

Once won over, the elder Migliaccios embraced what was to become Conundrum, with Vincent helping his son remodel the place in the evenings after the deli closed and Vince's shift at Spring Point had ended. Vince's girlfriend, Erin Meuse, who had been working at the deli since the Migliaccios opened it, pitched in on the preparations for Conundrum, doing everything from designing the art on the tabletops to helping develop the menu.

The early days were tough, at least in part because a planned June 2000 opening stretched to November — not exactly the ideal time to launch a restaurant in Maine — due to construction delays. "We opened the doors to a small group of people," Vince Migliaccio says with a laugh. "It was horrible. We didn't have a lot of money for advertising. But the bonus was we didn't have large overhead."

Eventually, while the Migliaccio family kept Conundrum on life support, word of mouth and a few well-timed reviews helped the restaurant's reputation spread. These days, Conundrum is busier in the winter than it is in the summer, thanks to a loyal population of locals who visit frequently. On a recent visit, the rivalry between Freeport and Falmouth's high school basketball teams was a hot topic among the adults quaffing beers and a few glasses of wine at the leather couches in the back. (The elder Migliaccios recently sold the deli to their other son, Joseph, and his wife; Vince thinks his parents may have retired from the food business for good this time.)

Migliaccio attributes the restaurant's success in large part to the accessibility of the menu he and Meuse, Conundrum's chef, continue to tweak. "I want you to come in and have something you're mostly familiar with," he says of items such as Italian sausage puttanesca and a grilled chicken and brie sandwich. "If you want to try something a little more exotic" — like pork loin rubbed with Moroccan spices and topped with mango chutney — "we've got that, too. That's really the way I eat."

His laid-back philosophy extends to the service — "What my servers might lack in old-school wine knowledge, they make up for in youthful enthusiasm," he says — and even to his dessert offerings, which change frequently depending on what he thinks tastes good among several local and regional purveyors' offerings. "We just don't have enough time in the day to do it ourselves, and if they can do it better, why not?" he says, unconcerned with what more image-conscious restaurateurs might see as an admission of imperfection.

But don't mistake Migliaccio's affection for comfort and accessibility for lack of attention to detail. "If you ask my kitchen or my servers, I'm a nightmare," he says. "I'm on their backs constantly, but that's because we're trying to achieve something here. I want a guy in a three-piece suit to be able to sit down with a $1,000 bottle of wine and another guy to get off a boat in ripped jeans and get a pint — and have no one bat an eye. It's a really hard feeling to achieve."

The best part about it? At Conundrum, Migliaccio makes it look easy.

Conundrum Wine Bistro is located at 117 Route 1 in Freeport. The restaurant will be closed from February 26 to March 29, with a reopening party and wine tasting on March 30. Conundrum serves dinner Tuesday through Saturday from 4:30 p.m. Reservations accepted for groups of five or more. 207-865-0303.