Boston: From Chowder to Cannoli: The Ultimate Boston Food Tour

Boston may be known for its rich history and charming cobblestone streets, but it’s also a heavyweight when it comes to food. This city serves up more than just clam chowder (though yes, that’s on the list). From buttery lobster rolls to sweet cannolis and perfectly crisp fried clams, Boston’s culinary scene is a delicious mix of old-school tradition and bold new flavors. Whether you're a local or just passing through, here are the must-try bites that prove Beantown knows how to bring it to the table.

Roast beef sandwich — Kelly’s Roast Beef

At Kelly’s Roast Beef, the Roast Beef Sandwich is a Boston legend that has stood the test of time. Originating in 1951 on Revere Beach, this sandwich features thinly sliced, tender roast beef piled high on a butter-toasted sesame bun. Often ordered "three-way" with American cheese, mayo, and their signature barbecue sauce, each bite delivers a harmonious blend of savory flavors and satisfying textures. It's no wonder that during peak months, a single location can sell over 20,000 of these iconic sandwiches, solidifying its place in Boston's culinary history.​

Steak tips — NewBridge Cafe

Tucked away in Chelsea, just north of Boston, NewBridge Café serves up steak tips that are nothing short of legendary. These sirloin tips are marinated in the restaurant’s secret barbecue sauce, then grilled to perfection, resulting in a tender, flavorful bite that has earned them the title of “Best Steak Tips” in Boston . Served alongside their signature home fries and a side of hot cherry peppers, this dish offers a harmonious blend of smoky, sweet, and spicy flavors. It's a must-try for anyone seeking an authentic taste of New England's culinary traditions.​

Cream of Wheat — Neighborhood Restaurant

At The Neighborhood Restaurant & Bakery in Somerville, the humble cream of wheat transforms into a breakfast legend. Served in a generous white bowl and dusted with cinnamon, this dish is rich, creamy, and comforting—a testament to the restaurant's Portuguese-American roots . It's no surprise that Boston Magazine honored it as the city's best in 2023 . Whether you're a local or just visiting, starting your day with this iconic porridge is a must.​

Baked Alaska — Oleana

At Oleana, the Baked Alaska is a dessert that defies expectations and redefines indulgence. This showstopping creation features a base of chewy coconut cake topped with a dome of velvety coconut ice cream, all encased in a beautifully torched meringue. The entire confection is then set afloat in a vibrant pool of passion fruit caramel, adding a tangy contrast to the sweetness. The result is a harmonious blend of textures and flavors that has earned accolades from food critics and dessert enthusiasts alike. 

Cannoli — Mike’s Pastry

No trip to Boston is complete without a visit to Mike’s Pastry in the historic North End, where the cannoli reigns supreme. Since 1946, this iconic bakery has been delighting locals and tourists alike with its legendary cannoli, making it a must-visit tradition for anyone in the city. With nearly 20 flavors to choose from, including classics like ricotta and chocolate chip, as well as creative options like limoncello and amaretto, there's a cannoli for every palate. Each cannoli is a perfect blend of crispy shell and creamy filling, offering a taste of Italian tradition right in the heart of Boston. Just be prepared for a bit of a wait, as this cannoli hotspot often has lines out the door—but trust us, it's worth it.

Lobster roll — Neptune Oyster

At Neptune Oyster in Boston's North End, the lobster roll is a culinary masterpiece that has earned its place among the city's most iconic dishes. Served either hot with clarified butter or cold with a touch of mayo, this roll is generously packed with succulent chunks of lobster tail, claw, and knuckle meat, all nestled in a perfectly toasted brioche bun. The combination of sweet, tender lobster and rich, buttery goodness creates a flavor profile that's both indulgent and unforgettable.

Fenway Frank — Fenway Park

At Fenway Park, the Fenway Frank isn't just a hot dog—it's a cherished Boston tradition that has delighted fans for generations. Introduced shortly after the park's opening in 1912, these iconic franks are crafted by Kayem Foods, who enhanced the original recipe in 2009 with a special blend of spices and meats, adding a bold flavor while preserving the classic taste. Prepared by boiling and then lightly grilling, Fenway Franks offer a juicy interior with a satisfying snap, all nestled in a soft, split-top bun. Whether topped with a squirt of yellow mustard or piled high with relish, enjoying a Fenway Frank at a Red Sox game is a must, embodying the essence of America's favorite pastime in one delicious bite.

Bar pizza — Poopsie’s

For a true taste of South Shore bar pizza, head to Poopsie's in Pembroke. This beloved local spot serves up 10-inch pies with a signature ultra-thin, crispy crust that's loaded edge-to-edge with bubbling cheese and your choice of toppings. Whether you go classic with pepperoni or adventurous with ghost pepper cheese, each bite delivers a satisfying crunch and rich flavor. The no-frills, retro atmosphere adds to the charm, making Poopsie's a must-visit for pizza enthusiasts seeking an authentic Massachusetts experience.

Boston Cream Pie — Omni Parker House

At the historic Omni Parker House in Boston, the Boston Cream Pie isn't just a dessert—it's a slice of culinary history. Created in 1856 by French chef Sanzian, this iconic treat features layers of golden sponge cake filled with rich pastry cream and topped with a glossy chocolate glaze . Despite its name, it's technically a cake, but that hasn't stopped it from becoming Massachusetts' official state dessert . Served in the elegant surroundings of Parker's Restaurant, indulging in this classic is like taking a delicious bite out of Boston's storied past.

Fish and Chips — Yankee Lobster

At Yankee Lobster in Boston, the Fish and Chips are a crispy, golden dream come true. Picture this: perfectly battered fish, fried to a crispy perfection, with a tender, flaky inside that practically melts in your mouth. Paired with thick, hand-cut fries that are the perfect balance of crunchy and soft, this classic dish is a no-brainer for any seafood lover. Whether you're strolling through the Seaport or just craving some comfort food, Yankee Lobster's fish and chips are sure to hit the spot and make you feel like a true New Englander!

From buttery lobster rolls to creamy Boston cream pies, Boston is a city that knows how to satisfy your cravings. Whether you're noshing on a Fenway Frank at the ballpark or diving into a bowl of clam chowder by the waterfront, each dish is a delicious adventure. Head over to hellozeal.ai and book any of these restaurants in seconds! So, grab your fork (and your appetite) because Boston's food scene is waiting to take you on a flavorful ride you won’t forget!