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He’s a trendsetting tycoon, dressed to the nines and looking to grab a quick gimlet before the 5:10 p.m. train. He steps through a set of nondescript white double doors and into a warmly lit room with a gleaming bar and rich wooden decor, the bartender polishing glasses as throngs of fellow patrons sip and converse. Checking his pocket watch, he casually strolls up to choose his chair. I’m going to like it here, he thinks, smiling.

Conceptualizing a space based on a particular picture of your clientele—be it tourist-casual or local luminary—would seem a fairly common practice for a restaurant owner. For Massimo Morgia, owner of Ristorante Massimo in Portsmouth, New Hampshire, the inspiration for Upstairs at Massimo’s, which opened last August, was considerably more particular.

“My nephew and I envisioned this character, an oil tycoon from the 1920s,” Morgia recalls of first formulating the concept for his restaurant’s new, aptly-named, ground-floor sister operation. “After a while, we had convinced ourselves that this person actually existed.”

In 1994, Morgia and a partner opened Anthony Alberto’s Ristorante Italiano in this space; when he became sole proprietor in 2007, he renamed it Ristorante Massimo. Last summer, upon hearing that the long-standing Paradise Gift Shop had officially gone up for sale, Morgia decided to roll the dice on an operation he hoped would help round out the Penhallow Street restaurant’s already sterling reputation.

“As nervous as I was about taking it over, especially when we saw the economy doing this,” Morgia says, using a diving-airplane hand gesture to signify the downturn in the economy, “I gave myself little panic attacks thinking about it. But after doing my due diligence, we decided to move forward, and it’s been tremendous.”

Situated in an old Federal customhouse—the quintessentially New England brick building just celebrated its 200th anniversary in 2013—Morgia’s commitment to “world-class Italian cuisine” is, by now, well known. But Morgia wanted something a bit different for Upstairs—a more casual vibe, but also one that offered enough in the way of consistency to make the transition between the two spaces as seamless as possible.

“It was important that it had the right feel, that it fit with the downstairs, that there was a natural flow, while respecting this 200-year-old building as well,” Morgia says. “So all of that came into play when we were putting the concepts together, and we’ve been pretty thrilled with the way it came out.”

As well he should: from the custom-made pewter bar to the antique, two-blade, belt-driven fans, the bar alcove’s deep-cherry gloss to the refrigerated wooden drawers refashioned from old library catalog drawers, Upstairs captures a time and a place in a way that is both earnest and authentic without being campy.

Downstairs/Upstairs

The project wasn’t without its fair share of challenges, however. While the original stairs connecting the basement-bound Massimo and its first-floor annex provided the perfect go-between, the lone wall that partitioned the restaurant and gift shop was rife with obstacles—namely, most of the building’s principal wiring, water, and sewer lines.

“I learned pretty early on in this process that, if you ask, ‘Can it be done?’ The answer is always yes,” Morgia says. “Anything can be done in these old buildings. But I learned to ask, ‘How many men, and how many days?’ At that point I could do the math myself.”

Morgia cited a number of people for helping bring about the space’s transformation: his nephew Morgia, the former restaurant manager for celebrity chef Thomas Keller and, as it turns out, a visionary designer, provided the initial sketch for the space’s distinctly Atlantic City feel. To help bring his 1920s concept to full, ornate fruition, Massimo turned to Lisa DeStefano of the eponymous, Portsmouth-based DeStefano Architects—the driving force behind efforts to connect the upstairs and downstairs quarters—as well as builder-designers Louis Hamel and Tricia Tobey of Tobey Designs.

“Once we realized we could connect the two spaces, the opportunities just exploded, knowing what the benefits would be to the business,” DeStefano says. “Having the strong presence on the street, we could imagine passers-by looking into the expansive glass and seeing the shimmering lights, the warmth of the space and the energy of the patrons drawing them in.”

Tobey agrees, citing her firm’s work as an opportunity to help accentuate the space’s vintage verve. “Taking that idea or vision and bringing it to reality is always fun with any client, whatever the concept is,” Tobey says, noting the shimmering mica surrounding the ceiling light fixtures and studded nail work as especially reflective examples. “The thinking being, OK, how are we going to make this happen with contemporary products?”

Thought for Food

As for the menu, well, that’s all Morgia and Executive Chef Jethro Loichle. To be sure, some of Upstairs’s menu items—the fresh-made pastas and from-scratch sauces, the ever-popular charcuterie of Italian cured-meat staples and world-inspired cheeses—are merely smaller-sized Massimo holdovers.

Others, such as the prosciutto-wrapped scallop with cauliflower puree and the grilled bear’s head mushroom with preserved lemon and watercress—just two of the offerings on Upstairs’s monthly updated mezza menu—serve as playful, whimsical riffs on a well worn foundation.

Like many restaurateurs in the region, Morgia and Loichle do their best to source products from as many local vendors as possible. “When I hear about the ‘trend of sourcing local,’ I think, that’s what Italians have been doing forever—sourcing locally,” notes Morgia, who was born outside of Rome and whose family still visits the Seacoast occasionally. “It’s a big part of what’s made the city a culinary destination.”

Having fostered a phenomenally loyal local following, Morgia says he believes Upstairs can serve a kind of dual purpose: to draw in first time visitors who may not be privy to Massimo’s distinctly tucked away location, while giving regulars the occasional casual respite.

History Lesson

After giving me the rundown on Upstairs, Morgia guides us back to the lower-level establishment that bears his name. This time, the interplay becomes much more immediate: from a Hemingwayhighball to the merlot-tinted ambience of Massimo’s brick buttressed walls, now peppered with paintings of Mediterranean sunsets and Sicilian shorelines.

Of the myriad materials Morgia shows me—menus, promotional items, and the like—none incites his excitement quite like the manila folder containing black and white images of the building at various stages of its centuries-old existence, downloaded from the National Historic Society’s website. Spanning from roughly 1910 to 1950, the photos paint a picture of how Portsmouth’s economy has evolved: from crudely-paved roads to masses of overhanging wires to window-fixed sale signs (“Women’s shoes: $1.49”), the building’s history is thrown into stark relief. And that’s just the 20th century. Fast forward to 2014, the picture is one of ever-unfurling accolades: Inc.’s Hottest Small City, Money magazine’s Top 10 Best Places to Live, and one of America’s Most Romantic Towns, according to Travel + Leisure.

Massimo wasn’t without its precedent, however: according to Morgia, another Italian restaurant, Anthony’s Al Dente, thrived here many years before—and was empty for more thereafter—before being resurrected anew under Morgia. Today, a full two decades after he first opened, it’s difficult to imagine any other owner overseeing the attendant culinary excellence.

Needless to say, Morgia prays the work he’s put into his latest labor—a space both time-tethered and timeless—will help leave a legacy by inextricably linking his business and the building in which it was born. “I am so humbled to be part of such an amazing city,” Morgia says. “It reminds me a lot of my Italian heritage, with its traditions and landmarks, and working in a 200-year-old customhouse only speaks further to that. It’s about respecting the city and being a pillar here for years to come.” 

And if that tycoon stops by, his gimlet will be ready.