THE RED CARPET felt different under Brendan Sullivan’s feet as he walked past some of the biggest names in American cuisine. Around him, celebrity chefs and restaurateurs who had graced magazine covers and television screens mingled in the lobby of Chicago’s Lyric Opera House. This was the James Beard Awards ceremony—the Oscars of the food world—and Sullivan, the third-generation owner of a seasonal hot dog stand in South Boston, was about to accept one of the industry’s most prestigious honors.
“This James Beard America’s Classics Award is not just for the Sullivan family, it’s for the entire city of Boston,” Sullivan said of that June evening. The weight of representing not just his family’s legacy, but an entire community’s story, was palpable.
Sullivan’s Castle Island—affectionately known as “Sully’s” to generations of Bostonians—was been named a James Beard America’s Classic for 2025, joining an exclusive club of regional establishments that have achieved “timeless appeal” and become integral to their communities’ cultural fabric. They were the only Massachusetts restaurant to win a James Beard Award in 2025.
The Chicago Moment
The ceremony itself was a whirlwind. Sullivan and his wife Adrienne, who co-owns the restaurant, found themselves seated among culinary luminaries whose names they’d known from cookbooks and television. The America’s Classics category celebrates restaurants that may not have the flash of upscale dining establishments but have earned something perhaps more valuable: the unwavering loyalty of their communities across decades.
“This award is not only a recognition of our commitment to serving outstanding food but also a celebration of the traditions that have defined Sullivan’s for generations,” Sullivan says. “We are deeply honored to be recognized among America’s Classics and to continue our legacy of bringing people together over great memories. This is not just an award for us: this is an award for all of New England.”
The James Beard Foundation’s citation captured what makes Sullivan’s special: “Every Bostonian has a story about Sully’s—whether from working there after school as teenagers, having their sports team or fundraiser supported by Sully’s, taking their children for some crinkle cuts like their grandparents took them, or simply enjoying it as a nostalgic seaside gathering place for locals.”
The Foundation: 1951 and Beyond
The story begins with Dan Sullivan, Sr., who in 1951 set up a hot dog stand near the shores of Castle Island. Post-war Boston was changing rapidly, and Sullivan recognized that families needed an affordable place to gather and enjoy simple, good food. His vision was uncomplicated: quality ingredients, reasonable prices, and a welcoming atmosphere where anyone could feel at home.
“My grandfather understood something fundamental about community,” Brendan Sullivan explains. “We focus on connection, community, and creating a space that unites people across generations. That’s the Sullivan’s philosophy.”
The original stand was barely more than a cart, but it occupied premium real estate: Castle Island, with its historic fort and waterfront views, was already a destination for Boston families seeking respite from city life. Sullivan’s timing was perfect. As Boston’s economy boomed in the 1950s and 1960s, so did the appetite for casual dining experiences that felt authentically local.
Dan Sullivan, Jr. took over operations in the 1970s, expanding the menu to include the thick crinkle-cut fries and double smash burgers that would become Sullivan’s signatures. The restaurant’s evolution reflected broader changes in American dining—the rise of fast-casual food, the growing appreciation for regional specialties, and the increasing importance of authenticity in an era of corporate chain restaurants.
By the time Brendan Sullivan assumed leadership, Sullivan’s had become more than a restaurant; it was a Boston institution. The seasonal nature of the operation—opening in March and closing in November—created an annual rhythm that became part of the city’s cultural calendar. The March opening is still considered by many locals as the true beginning of spring. A short drive down the south shore, you’ll find Sullivan’s second location, at Hanover Crossing, which is open year-round.
The People’s Palace
What sets Sullivan’s apart from other successful regional restaurants is its democratic ethos. Unlike establishments that cater to specific demographics or price points, Sullivan’s serves everyone equally. There are no reservations, no VIP sections, no shortcuts to the counter. Senators and construction workers, tourists and longtime residents—everyone waits in the same line.
“The sense of community is what sets it apart,” Adrienne Sullivan observes. “Regardless of how long you’ve lived in Boston or if it’s your first day there, everyone waits in line as equals. There are no VIPs. If you’re uncertain about what to order, just ask the person in line next to you. Everyone arrives as strangers and departs as friends.”
This philosophy has created a unique social dynamic. Maria Santos, a Dorchester resident who has been bringing her family to Sullivan’s for over three decades, describes it as “Boston’s living room.” She adds, “I’ve seen my kids grow up in that line, watched them bring their own children. It’s where we go to celebrate, to comfort ourselves, to just be together.”
The restaurant’s role extends beyond individual families. Local sports teams celebrate championships with Sullivan’s catering. High school seniors mark graduation with one last group meal before heading off to college. The restaurant has become a touchstone for life’s major moments, both joyful and challenging.
“After 9/11, people needed somewhere to go, somewhere that felt safe and familiar,” Brendan Sullivan remembers. “We stayed open later that week, and the line was longer than usual. People weren’t just coming for the food—they were coming for the community, for the connection.”
The Menu: Evolution and Tradition
Sullivan’s menu reflects both continuity and change. The hot dogs that built the business remain largely unchanged—simple, high-quality, served with care. But the menu has expanded to reflect Boston’s evolution as a food city and the growing sophistication of diners’ palates.
The lobster rolls, introduced in the 1980s, have become perhaps the restaurant’s most celebrated item. Made with fresh, locally-sourced lobster meat and served on a house-made roll, they exemplify Sullivan’s approach: take a classic preparation and execute it flawlessly without unnecessary complexity.
“One of our signature dishes is our double cheeseburger, and we’ve had it since 1951,” Brendan Sullivan notes. “It’s not fancy, but it’s perfect. The beef is fresh, the cheese is melted exactly right, and it’s served on a bun that’s been grilled to the perfect temperature. Sometimes simplicity is the highest form of sophistication.”
The crinkle-cut fries deserve special mention. Cut fresh daily and cooked in small batches, they’ve achieved something approaching legendary status among Boston food enthusiasts. Food writers have attempted to decode their appeal, but customers need no explanation. They’re simply part of the Sullivan’s experience.
Recent additions to the menu reflect contemporary tastes while maintaining the restaurant’s core identity. Fresh seafood options have expanded, vegetarian choices have been added, and seasonal specialties now rotate throughout the year. But the changes are implemented carefully, with deep consideration for how they fit into the Sullivan’s tradition.
“We’re not trying to be cutting-edge,” Adrienne Sullivan explains. “We’re trying to be timeless. Every addition to the menu has to pass the test: is this something that will still make sense in twenty years? Will it honor what we’ve built here while serving our customers’ evolving needs?”
Rickey Business: The Newest Collaboration
The James Beard Award opened new possibilities for Sullivan’s, including collaborations that might have seemed unlikely just a few years ago. The partnership with Castle Island Brewing Company to create “Rickey Business,” a raspberry-lime lager inspired by Sullivan’s signature raspberry lime rickey, represents the kind of creative thinking that emerges when tradition meets innovation.
“We wanted a way to encapsulate that fleeting taste of summer! Our signature raspberry lime rickey—the sweet, citrusy, crispy cold refreshment classic we are known for has been reimagined with a twist! Sullivan’s Castle Island teamed up with our amazing neighbors at Castle Island Brewing to create ‘Rickey Business’, a raspberry-lime lager. We couldn’t think of a better way to celebrate our James Beard America’s Classics award with this cool community-based collaboration—the essence of what makes us all proud Bostonians, and to be able to support a meaningful foundation that does so much for our industry. Cheers!” Brendan Sullivan explains.
The collaboration made perfect sense geographically and philosophically. Castle Island Brewing, founded by Adam Romanow, shares Sullivan’s commitment to quality and community connection. Both businesses understand that success in Boston requires more than just good products—it requires becoming part of the city’s fabric.
“We couldn’t be more excited to team up with Sullivan’s on this one,” Romanow says. “Castle Island has always been a place that brings people together, and Sullivan’s has done that for generations. They’re a Southie staple, and now a James Beard Award winner—we’re proud to celebrate that success with a beer that’s as bright and refreshing as they are.”
The beer itself represents something larger than a simple business partnership. It’s a recognition that Sullivan’s has achieved the kind of cultural significance that can be translated into other mediums while maintaining its essential character. The raspberry-lime flavor profile that has defined Sullivan’s rickeys for decades now exists in a form that can be enjoyed year-round, extending the restaurant’s seasonal presence into the broader Boston food scene.
“Rickey Business is all about good times with great people,” Romanow continues, “which made this collab a no-brainer.”
The Future: Honoring the Past, Embracing Tomorrow
As Sullivan’s celebrates its 75th season, the restaurant faces the challenge that confronts all successful family businesses: how to honor the past while remaining relevant to future generations. The James Beard Award has elevated Sullivan’s profile significantly, bringing new attention and new expectations.
“Everyone has a Sullivan’s story. It’s not just a meal. It’s an experience, an institution. This recognition reinforces our commitment to not only honor our past but also to embrace the future,” Sullivan said. “We’re dedicated to expanding our offerings and reaching new patrons, all while keeping the spirit of old Boston alive for every customer who walks through our doors.”
The expansion to a year-round location in Hanover represents one approach to growth—extending the Sullivan’s experience beyond its seasonal Castle Island home while maintaining the core values that make it special. The Hanover location serves the same menu with the same attention to quality, but it also allows the family to experiment with new offerings and serve customers who might not be able to make the trip to Castle Island.
The Legacy: More Than Food
What emerges from conversations with the Sullivan family, their employees, and their customers is a clear understanding that Sullivan’s success transcends food service. The restaurant has become a repository of Boston’s collective memory, a place where the city’s identity is reinforced and celebrated daily.
“The James Beard Foundation recognizes restaurants that are woven into the fabric of their communities, and that’s exactly what we strive to be. Sullivan’s is a place where generations gather, where traditions are passed down, and where a simple meal can mean so much more.”
The stories customers share reveal the depth of Sullivan’s impact. There are marriage proposals on the seawall, birthday celebrations that span decades, first dates that led to lifelong partnerships, and family traditions that have been passed down through generations. The restaurant has become a stage where Boston’s human drama unfolds, one paper boat of fried clams at a time.
Dawn Padmore, VP of Awards at the James Beard Foundation, captured this significance in her statement about Sullivan’s selection: “Sullivan’s is a wonderful expression of what a James Beard America’s Classic is—good food, timeless appeal, and a great example of the breadth of American cuisine. We were excited to celebrate them at the Awards in June, and we wish the Sullivan’s team many more years of its continued role as a pillar of its community.”
The Eternal Return
As summer 2025 heats up, the restaurant’s impact on Boston’s culinary landscape has never been more apparent. The James Beard Award has brought national attention, but it hasn’t changed the fundamental experience of waiting in line for a lobster roll while watching boats navigate Boston Harbor.
“I am incredibly honored that our restaurant has been recognized as an America’s Classic by the James Beard Foundation. This award is about more than just food—it’s about tradition, community, and the people who have made this place special for generations,” Brendan Sullivan says. “This is not just an award for Sullivan’s—it’s an award for Boston. It honors the countless families, friends, and visitors who have made memories with us over the years.”
The restaurant’s seasonal closure, once simply a practical necessity, has become part of its mystique. The anticipation that builds over the winter months, the excitement of the March reopening, the melancholy of the November closing—these rhythms have become part of Boston’s emotional calendar.
For the Sullivan family, the James Beard Award represents both recognition and responsibility. They are now the stewards of not just a family business, but a cultural institution that means something profound to their community. The award acknowledges what locals have always known: that Sullivan’s matters in ways that extend far beyond the transaction of buying and selling food.
“Thank you to the James Beard Foundation for this incredible honor, to our loyal customers who have made Sullivan’s what it is today, and to the city of Boston for embracing us as a part of its history,” Brendan Sullivan concludes. “We are deeply grateful.”
As the sun sets over Castle Island and the last customers of the day make their way back to their cars, Sullivan’s Castle Island stands as proof that American success stories come in all forms. Sometimes the most profound impact comes not from revolutionary change, but from the patient, consistent work of bringing people together around something as simple as excellent food served with genuine care.
The story of Sullivan’s is ultimately the story of Boston itself—resilient, authentic, unpretentious, and deeply committed to community. In a world of constant change, Sullivan’s offers something increasingly rare: continuity, connection, and the simple pleasure of knowing that some things remain exactly as they should be.
That, perhaps, is the most lasting legacy of all.
