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Roast Beef 1000
Cutty’sAddress and Info
Piled high with slow-roasted beef, crispy shallots, Thousand Island dressing, and sharp cheddar -- all served on a brioche bun -- this sandwich is so popular that it makes up half of Cutty’s sales. But this sandwich doesn’t use just any ordinary roast beef. Owner and Chef Charles Kelsey creates his beefy masterpiece by giving a whole beef chuck roll an overnight dry cure with his own spice rub, then slow-roasts it in a low oven until it reaches its juicy peak perfection.
Union Oyster House
Union Oyster House is a historic landmark all on its own -- it’s been around since 1826, after all -- and it’s also the oldest restaurant in continuous service in the nation. 10 years after opening, Union Oyster House began serving steaming-hot bowls of their now-famous clam chowder. Made with just the right amount of potatoes, clams, butter, onions, and cream, this rich and chunky chowder has set the standard for the soup people think of when they think of Boston.
The Double Awesome
Venue NameAddress and Info
This vegetarian indulgence's crave-worthy deliciousness is sufficient to make it one of the newer entrants on this list. It's a scallion pancake sandwich with local greens pesto, Vermont cheddar, and two slow-poached and subsequently fried eggs -- because two eggs is obviously twice as awesome. Good enough for a late breakfast (they open at 11am), lunch, or dinner, this dish lives up to its name, especially when you bring their spicy ketchup into the mix.
Homemade Boston Baked Beans
Durgin ParkAddress and Info
Durgin Park made our city’s baked beans famous, and continues to keep their recipe one of the most coveted in the city and beyond. It's more than 150 years old, and utilizes salt pork, sugar, molasses, dry mustard, and onion to flavor the beans. With each nostalgic spoonful, it’s no wonder why their recipe has endured seemingly forever.
Local Grass-Fed Beef Burger
Craigie on MainAddress and Info
With only 18 burgers served at dinner -- in the bar area only -- locals know to get to Craigie on Main early if they want to bite into one of Chef Tony Maws’ signature grass-fed burgers. Served in a homemade bun and topped with Shelburne Farm cheddar cheese and house-made mace ketchup, the only thing that could make this meaty masterpiece better is adding a fried egg ($3) and/or (AND, always AND!) house-smoked bacon ($3).
Mike's PastryAddress and Info
When there’s a line out the door on a daily basis, you know you’ve got to be doing something right -- and Mike’s Pastry’s cannoli are definitely worth the wait. These delicate, handmade shells with rich ricotta-cream filling are worth flighting the crowds and the diabetes. Mike’s serves a multitude of cannoli flavors -- such as chocolate chip, pistachio, and limoncello, to name a few -- but honestly there isn't much improving upon the original plain ricotta.
Roast Chicken with Garlic, Lemon, and Parsley
Hamersley's BistroAddress and Info
You wouldn’t think a roast chicken dish would make a list of iconic dishes, but Hamersley’s Bistro is no ordinary roast chicken. Hence why it’s been on Chef Gordon Hamersley’s menu since the restaurant opened in the late 1980s. This incredibly juicy roast chicken possesses an irresistible brown crust, created by the parsley paste that’s rubbed on the bird before cooking.
Maine Lobster Roll
Neptune OysterAddress and Info
New England is known for having fresh, delicious lobster rolls, but only one local restaurant can make the most iconic one: and that’s Neptune Oyster. Neptune piles their toasted rolls high with chunks of fresh Maine lobster, making this sandwich worthy of all its praise. Neptune even caters to both sides of the lobster roll debate: theirs is available hot with butter or cold with mayonnaise. Served with fries, this is the essential Summer (and New England) meal.
Santarpio's PizzaAddress and Info
Sure, Boston has plenty of celebrated pizza places (hello, Regina’s), but this mozzarella, sausage, and garlic pie from Santarpio’s is one we can’t resist -- and many other Bostonians can’t, either. It’s the family-owned pizzeria’s most popular pie, and it’s dotted with flavorful sausage that’s made in-house. Another thing that makes this place (and its pizza) iconic? It’s been in business since 1903, and has won a slew of awards for its pies.
Egg in a Jar
West BridgeAddress and Info
Local food writers and everyday diners made this West Bridge appetizer a Boston phenomenon when it opened back in 2012. The dish consists of a poached duck egg served over hen of the woods mushrooms, pomme puree, and crispy duck skin. As if a rich, runny egg dripping down all of that deliciousness wasn’t enough, it’s also served in a convenient 7.5oz Ball jar to boot. Things just taste better in jars.
Boston Cream Pie
Omni Parker HouseAddress and Info
The Boston Cream Pie we know and love today was created at Omni Parker House -- the then-called "Chocolate Cream Pie" was served at the hotel (then known as Boston’s Parker House) when it first opened in 1856. Today, the custard-filled, chocolate-frosted "pie" is available in cake mixes and doughnut shops (to name a few) pretty much everywhere your sweet tooth can find it. But for the real, delicious deal, this original recipe is worth every dollar (and calorie).
1. Cutty's284 Washington St, Brookline
2. Union Oyster House41 Union St, Boston
3. Mei Mei506 Park Dr, Boston
4. Durgin-Park340 Faneuil Hall Market Pl, Boston
5. Craigie on Main853 Main St, Cambridge
6. Mike's Pastry300 Hanover St, Boston
7. Hamersley's Bistro553 Tremont St, Boston
8. Neptune Oyster63 Salem St, Boston
9. Santarpio's Pizza111 Chelsea St, Boston
10. West BridgeOne Kendall Square, Cambridge
11. Omni Parker House60 School St, Boston
Cutty’s is the patron saint of sandwiches. If you're stopping into the Brookline Village shop for breakfast, you have inventive options at your fingertips like a Thai sausage sandwich and an eggs-Benedict-wich, but Cutty’s Egg Sandwich is always a solid choice, composed of eggs whipped with butter, sharp cheddar cheese, and either spicy Sriracha aioli, truffle ketchup, or red-eye mayo on Iggy’s black pepper brioche. For lunch, Cutty's Roast Beef 1000 is the must-order, piled high with house-roasted meat, crispy shallots, and sharp cheddar drizzled with Thousand Island dressing on brioche. Even noted car-driver Guy Fieri approves of the sandwiches here. Whether that makes you want to visit more or less is your prerogative.
Ready for this claim to fame? Union Oyster House is the oldest restaurant in America, serving up mussels, chowders, lobster, and (of course) oysters in Government Center since people like Daniel Webster were alive and slurping back shellfish here. Its big, red rooftop sign lights the way like the North Star, a landmark in the neighborhood, leading people to this rustic, buzzy space, where the New England staples (or, as the menu states, "Ye Olde New England Favorites") are a must: steamers, clam chowder, boiled stuffed lobster, baked beans, and Indian pudding.
Specializing in creative Chinese-American cuisine, Mei Mei is the brick-and-mortar incarnation of the beloved food truck of the same name. The 36-seat space is livened by bright yellow chairs, walls lined with Sriracha, and an open kitchen, where crispy dumplings (and pierogi), dan dan noodles, vegetable-packed curries are made. Stop in during lunch for the Double Awesome, a scallion pancake sandwich made with pesto, cheddar, two eggs, and your choice of protein (cottage bacon, ham or turkey). There’s also a takeout-only menu equipped with late-night items like hot dog & kimchee fried rice, sweet corn fritters, and, naturally, the Double Awesome.
Aside, maybe, from the Freedom Trail, it doesn't get much more historic than Durgin-Park in Faneuil Hall. Technically, this restaurant dates back to the pre-revolution days, but it's been operating under its current name and location for around 200 years, so these guys know what they're doing. Fresh local and imported fish makes for the best New England staples (clam chowder, lobster bisque) and bread baked in-house makes for unbeatable burgers and sandwiches. Just beware, Durgin-Park flaunts its history loud and proud, so it's a little touristy.
Chef and owner Tony Maws' Craigie on Main serves French-accented bistro food in Central Square. The à la carte and tasting menus are constantly changing with exciting new dishes, but one signature remains: The Burger. The half-pound patty blends brisket, short rib, bone marrow, and suet into one unforgettable burger that reached peak food fame when it graced the cover of Bon Appétit.
Mike’s Pastry, the Hanover St. mainstay, has been drawing crowds of cannoli-craving hopefuls (read: lines down the block, at all times) to its North End storefront since 1946. Mike’s features nearly 20 different flavors of il cannolo, as they call it, piped into crunchy, fried pastry shells (that somehow don’t crumble at first bite), and dusted with powdered sugar. The options are vast, but when you hit the pastry case, time is of the essence: pick your poison, fill your iconic white and blue pastry box, and move along -- there are dozens of others waiting to do the same.
Upscale American cuisine awaits you at Hamersley's -- you won't go wrong with anything on the menu, but they are unusually famous for a roasted chicken entree that you shouldn't miss.
Bivalves are king at Neptune Oyster, a popular seafood counter in the North End. The menu is classically New England but a variety of seafood-based recipes come out of the kitchen, from cioppino and fried Ipswich clams to fish & chips and Basque-peppered Spanish octopus. Served two ways, the lobster roll is an award-winning signature, and though it's prepared the typical way with mayonnaise, the hot butter option is the way to go. Neptune draws hoards of seafood-craving hopefuls to its Salem St. storefront on weekend afternoons and evenings, so be prepared to traverse the neighborhood while you wait for your coveted seat at the marble bar.
Santarpio's Pizza has been around since 1903, so when we say “old-school,” we mean it. Much to the dismay of certain Bostonians, Santarpio’s is known for its New York-style pies, whose chewy crusts are thick and crispy enough to bear the weight of the generously distributed Italian cheese and sauce. Keep it simple with a cheese pizza, or get the sausage & garlic pie for a kick of meat. Santarpio's is far from a one-hit wonder though: its skewers of lamb and steak tips make up a solid barbecue option, as does the house-made sausage on its own. The East Boston location is cash-only, so spare yourself a scolding from one of the notoriously cranky serves and head to the ATM beforehand.
Housed in the historic former Boston Woven Hose & Rubber Factory and sporting the original name of the Longfellow Bridge, WB's the inaugural eat/drinkery from a couple of Aquitaine alums who wanted to sling tasty 'tails alongside a lineup of modern French sustenance with "a New England perspective" -- so be prepared for your food to grumble suspiciously about this year's unseasonably mild Winter.
Billed as Boston's oldest and most storied hotel, this historic, 551-room landmark opened downtown in 1855 and lays claim to having hosted literature's legendary Saturday Club (Longfellow, Emerson, Oliver Wendell Holmes), inventing the Boston Cream Pie, and serving as ground zero for JFK's no-doubt-epic bachelor party.