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The North Shore of Boston has always been home to visionaries—restaurateurs, hoteliers, cultural leaders, and entrepreneurs who shape not only the region but also set trends far beyond its borders. From the kitchens of celebrated chefs to the boardrooms of innovative business leaders, their stories reveal a shared passion for creativity, community, and legacy. These legends—whether preserving farmland, reimagining historic landmarks, or redefining hospitality—remind us that the North Shore is more than a destination. It’s a living, thriving stage where tradition meets reinvention, and where the next chapter of New England’s cultural heritage is constantly being written.

Culinary entrepreneur Joe Faro has done it again. In September 2024, Artisan Chef Manufacturing (a venture of Faro’s company Tuscan Brands and Sal Lupoli) acquired Buitoni Food Company. With this acquisition, Faro is revitalizing the iconic Italian-American brand and its operations in both Massachusetts and Virginia. The results will be delicious.

Earlier this year, Sal Lupoli, founder of Sal’s Pizza and CEO of Lupoli Companies, launched King Street Crossing in Littleton on the former IBM campus. After a groundbreaking ceremony in May (complete with shovels), this 50-acre mixed-use redevelopment will deliver residential units, a hotel, retail and restaurant spaces, and office facilities.

The big announcement this fall for Anna Rossi is her return to broadcast television via an exciting new partnership with Boston 25. The Emmy-nominated chef and lifestyle guru began a brand-new morning news segment last June covering food, entertaining, and seasonal inspiration.

We have amazing news for anyone who loved Oh $#!% What’s for Dinner ? by Emmy Award-winning author Maria Sansone. Sansone is currently working on her second cookbook, which will focus on entertaining made easy, complete with crowd-pleasing recipes and hosting tips.

As the CEO of the Trustees, the nation’s first and largest land conservation organization, Katie Theoharides has committed to conserving more than 12,000 additional acres of farmland, forests, and coastline over the next five years. In addition to landscapes, she also has made it the organization’s mission to increase community garden acreage in Boston by 20 percent.

Longtime professional partners Billy Costa (beloved radio host) and Jenny Johnson (award-winning producer) have released a 272-page cookbook that is no less than a love letter to the Boston food scene. With a forward by Mark Wahlberg, A Taste of Boston delivers 60 recipes assembled from notable city chefs and restaurateurs.

Kristina Crestin / Photograph by Doug Levy

Jonathan Knight of Farmhouse Fixer fame (which he hosted on HGTV with business partner and noted North Shore interior designer Kristina Crestin) has returned to his pop star roots. He joined New Kids on the Block’s first-ever Las Vegas residency titled “The Right Stuff.” This show at Park MGM mixes boy band nostalgia with Vegas spectacle and runs through February 2026.

For Kristina Crestin alongside her interior design business, she is working out some ideas on sharing her passion and knowledge about the process for renovations. “I geek out about what an effective process looks like to arm homeowners with the knowledge—now I am just playing around with what that means. Is it a youtube channel? Is it a book? In development …stay tuned.”

In 2025, Lt. Governor Kim Driscoll advanced a $16.6 billion capital plan to expand municipal grants, housing, and education access while also supporting early education and behavioral health programs. She further championed the arts by helping establish Massachusetts’s first Poet Laureate and promoting the creative economy as a driver of jobs and innovation.

Helmed by owner Sheree O’Reilly, Beauport Hospitality Group (parent company to Beauport Hotel, Cruiseport, Seaport Grille, and Beauport Cruiselines) is a major player in regional tourism. Beauport Hotel continues to rack up numerous “best of” awards, including taking home our 2025 BONS awards for “Best Hotel Bar.”

Brian Kelly of Kelly Automotive | Photographs by Joel Laino

In July, Brian Kelly of Kelly Auto Group was honored with Endicott College’s inaugural Distinguished Patron Award at the Misselwood Concours d’Elegance, an annual American classic car and motorcycle event. This award recognizes his successful entrepreneurial journey and role as an industry leader.

It was 40 years ago when Steve DiFillippo bought his first Davio’s location (there are currently 10) on Newbury Street in Back Bay. In honor of this big anniversary milestone, the chef/owner and his team celebrated in style with a star-studded one-night celebration in May 2025 at Davio’s Seaport.

Jenny Holaday I Photograph courtesy of Encore Boston Harbor

This year has been big for Jenny Holaday, president of Encore Boston Harbor. To start, she participated in the Dean’s Distinguished Speaker Series at Boston University’s School of Hospitality. And, as of late August, Encore has generated more than $1 billion in revenue for the Commonwealth of Massachusetts since opening in 2019. This 10-figure contribution has gone back into the state to support the Commonwealth and taxpayers.

Vin Cipolla By Shawn Henry

In July, Vin Cipolla, president and CEO of Historic New England, took part in the “Preserving Culture” conversation at the Norfolk Library, where he unveiled plans to transform Haverhill’s historic shoe factories into a vibrant cultural hub known as Haverhill Center. Meanwhile, he played a prominent role on the volunteer host committee for Historic New England’s 2025 Medal Gala, a high-profile event celebrating civic leadership in preservation.

There is always something exciting going on at North Shore Music Theatre (NSMT). Under the leadership of owner Bill Hanney, NSMT is promoting a 2025 subscription season that includes The Shark Is Broken, Waitress, The Wizard of Oz, Grease, Rent, and The Cher Show. Hanney has been actively promoting the lineup on local media, including a spotlight segment on WRKO.

The joining of Lark Hotels—under the leadership of founder Rob Blood— and Land Life House in December 2024 doubled Lark’s footprint, elevating its presence in the boutique hotel market with nearly $1 billion in assets. Wanderers can head to The Bow Hotel in Portsmouth, new this May. On the horizon is Cambridge Common House outside Harvard Square.

Aldi Companies founder Michael Aldi has been busy dreaming up his fifth concept to date. Finally, Mila’s, developed in partnership with Redgate, is open for business on Gibson Point in Revere. This day-tonight eatery features indoor and outdoor dining and a holistic menu reflective of the destination’s wellness focus.

Sports agent and Salem native Sean Stellato hosted the 17th Annual All-American Fundamental Showcase football camp in his hometown this summer, bringing together local talent to honor late athletes James Galante and Bryan Braman. Shortly afterward, his client, Tommy “Cutlets” DeVito, was claimed off waivers by the New England Patriots, marking an exciting new chapter headed into the NFL season. He’s also coming our with a new TV series on the horizon, Agent Stellato in the works.

Ron Martignetti and his eponymous hospitality group are completing a multimillion-dollar renovation of the Inn at Good Harbor Beach in Gloucester, updating the century-old property with modern amenities and access to a private stretch of beach. Scheduled to reopen later this year, this destination is sure to reclaim its former glory, and then some.

Alan Gibeley By Joel Benjamin

Giblees celebrated its 75th anniversary this year, marking a legacy of finely tailored menswear and family-led tradition on the North Shore. Not surprisingly, owner Alan Gibeley was honored by MR agazine with the prestigious Specialty Merchant of the Year award. It recognizes his retail prowess and ability to adapt and thrive in a competitive market.

Susan Kanoff, founder of Uncommon Threads and style influencer, has had an extraordinary year. She was honored with the prestigious Massachusetts Teachers Association Louise Gaskins Lifetime Civil Rights Award along with a Massachusetts State Citation for her work empowering women in need. In addition, her deeply personal chapter, “I Wasn’t Always a Butterfly,” appears in the newly released Midlife Private Parts by Dina Alvarez and Dina Aronson.

As founder and CEO of Bold Moves, a business coaching firm designed to empower women, Amy Pocsik has been making bold moves all her own. For starters, her first book will publish at the end this year. And she is once again hosting the annual Boston Women’s Leadership Summit, which brings together executives and entrepreneurs in many different industries.

It’s official: Social media strategist Armani Thao has officially launched a digital marketing company, FWA Creative, which specializes in social media marketing, brand strategy, and creative content production. The firm works with restaurants, hospitality groups, lifestyle brands, and small businesses to elevate their online presence.

Longtime Gloucester resident (his maternal grandparents lived there in a sea captain’s house) Bill Monahan made a name for himself (and an Oscar) by penning The Departed. But movie buffs take note: he also wrote the screenplays for Marlowe (2023), a neo-noir film starring Liam Neeson, and The Tender Bar (2021), a drama directed by George Clooney.