STORY BY Natalie Mcallister
PHOTOS BY Landon Vonderschmidt

Forget checkered tablecloths, mountains of spaghetti and meatballs and the sultry songs of Dean Martin. The Boot is kicking stereotypes for Italian restaurants straight to the curb.

Sometimes the best Italian restaurants are those where you expect to push open the kitchen door and find Mamma tending the stove. Tucked into a rustic brick building in Westport, The Boot (415 Westport Road) is laced with that sort of heritage. Owners Aaron Confessori and Richard Wiles can trace their roots back to Italy, and memories of grandmothers and family dinners seem slipped into the smallest of details at this cozy restaurant.

The Boot injects urban farmhouse charm into traditional Italian hospitality. Soft cloth napkins dress the wooden tables. A long center table spans the length of the dining room inviting strangers and big parties to spark conversation with their neighbors. Rustic ladders decorated with herb sprigs and whiskey jars stretch across the exposed brick walls, and bright red chairs add color to the reclaimed wood floors.

On the menu, dishes like the agnolotti al plin, a parsnip, pear and tarragon pasta ($12), or the porco picante meatballs ($7) are as authentically Italian as they are unexpected. The dishes crafted for The Boot seem to trace the shape of Italy itself, from seafood like the Prince Edward Island mussels with sauce pomodoro (Confessori’s favorite) to short ribs and quattro formaggi pizzas. Wiles returned to his great-grandmother’s cookbook for inspiration, and dishes like the risotto raggio—a porcini mushroom, prosciutto picante, grana padano and la quercia dish ($12)—are borrowed from her repertoire.

As with Wiles and Confessori’s neighbor restaurant, Westport Café and Bar, cocktails and highballs are menu mainstays. Highballs are kept simple, like grapefruit juice and Fernet Branca ($7), and are served in mason jars with crushed ice. More complicated cocktails, like the Bellini (prosecco, peach puree and house grenadine, $8) can be traced back to Italian tastebuds.

At long last, authentic Italian food and sip-worthy drinks are pieces finally added to the Westport puzzle. “There was a big need for an Italian restaurant in Westport,” Confessori says. “If you haven’t been to Westport in a while, it’s time to come back.”

See more photos here.