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22 things to put on your Boston bucket list
Watch a game at Fenway, compare cannoli in the North End or take a ferry far enough into the harbor to leave the traffic behind. A Boston bucket list should leave room for all three. It should also give you something to do when the weather refuses to cooperate. These 22 outings cover Boston and a pair of Cambridge museums. Some need tickets, some cost nothing, and a few belong to a particular season. Choose a neighborhood and build around one main activity. There is no prize for getting through the list before dinner. The Charles River Esplanade gives you paths beside the water, benches and views across to Cambridge. Start with a short walk instead of committing to a long river loop. Bring something to sit on if you want to stay for sunset, and use the pedestrian crossings over Storrow Drive to reach the park. Fenway Park makes baseball an afternoon or evening out in the neighborhood. Choose a seat with the sightline in mind, then leave time for food nearby. Our Fenway food guide gives you options before or after the game. When the team is away, official ballpark tours are another way inside. The Wilbur hosts stand-up comedians as well as musicians and other touring performers in the Theater District. Choose a show from its calendar rather than assuming every night is comedy. Read the seating and ticket details for the performance you want, then leave enough time for dinner that you are not checking the bill during the opening act. Modern Pastry and Mike’s Pastry give you the makings of a North End cannoli comparison. Buy from both if that sounds enjoyable, or skip the judging and order the filling you like. Modern also sells Italian cookies, cakes and other pastries. A cannoli does not have to become an argument, although Boston has had some practice. The Rooftop at The Envoy puts the harbor and downtown buildings in view above Sleeper Street. Save the outdoor seating for weather you actually want to sit in, and check booking terms before choosing a table. Our Boston rooftop guide has alternatives if your plans take you elsewhere. The Museum of Fine Arts and Isabella Stewart Gardner Museum are close enough to combine, but each can fill a visit on its own. Choose particular galleries at the MFA or spend time with the Gardner’s courtyard and densely arranged rooms. Check both calendars before committing to a day: the Gardner closes on Tuesdays, and admission arrangements differ. The Head of the Charles brings rowing crews to the river each October. Choose a viewing area using the regatta’s spectator information, then allow time to walk between it and your arrival point. River paths and bridges get busy during racing. Wear something warm enough for standing beside the water, not just the walk there. Row 34’s Fort Point restaurant occupies a former textile warehouse on Congress Street. Come for seafood, with a raw bar and lobster rolls among the choices. It works as a meal before or after a waterfront walk, though it is not directly on the harbor. Reserve the correct location: Row 34 also has restaurants in Kenmore Square and Cambridge. The Boston Common’s holiday lights make an after-dark walk worth putting on the winter calendar. Pair it with Frog Pond skating once the rink’s season opens, or stay on the paths and watch. Check the city’s announced tree-lighting date before planning around the ceremony; decorations and skating do not run all year. The Harborwalk connects waterfront stretches across Boston, with parks, wharves and places to sit along the way. Choose a manageable section around the Seaport, downtown or North End using the Harborwalk map. It is a network through several neighborhoods, so do not assume every section joins up without street crossings or detours. At the New England Aquarium, spend time with the penguins before working your way around the Giant Ocean Tank. Daily feedings and presentations give you a reason to pause rather than rushing from exhibit to exhibit. Book admission ahead for busy dates, and confirm the day’s presentation times at the information desk. TD Garden’s calendar covers concerts alongside Bruins and Celtics games. Pick the event first, then check the seating map for that particular setup. A concert floor and a basketball court produce different views from the same section. Use the venue’s event listing to reach the ticket seller, and read the bag policy before leaving home. Trillium’s Fenway taproom at 401 Park Drive has a patio and room for a beer. Bring your own food, or order from Time Out Market next door. Outdoor seating is seasonal. Leashed dogs are allowed on the patio. Boston Duck Tours combines a narrated ride past city landmarks with time on the Charles River in the same vehicle. Check the departure location when booking: tours leave from several places, including the Prudential Center and Museum of Science. It is useful for getting an overview of the city before deciding where to spend more time. Newbury Street gives you shops, galleries and places to eat along one Back Bay walk. Start toward the Public Garden if you want to continue through the parks afterward, or work in the other direction toward Massachusetts Avenue. Leave time to browse the smaller storefronts and upper floors rather than treating the street as a route between chain stores. Bring lunch to Boston Common or choose a patch of lawn on the Rose Kennedy Greenway. The Common works with a downtown or Beacon Hill walk; the Greenway fits a waterfront outing. Use the bins or take your rubbish with you. If the ground is wet, a bench and a sandwich still count as lunch outside. Sullivan’s Castle Island serves the sort of food that belongs after a walk: hot dogs, burgers, seafood and ice cream. Choose the Castle Island location when checking its menu and hours, since Sullivan’s also operates elsewhere. Leave time to walk beside Pleasure Bay and around the fort, rather than making the whole trip a queue for lunch. Georges Island has Fort Warren; Spectacle Island offers walking trails and harbor views. Seasonal ferry service determines which trip you can make, and not every island is served on every date. Read the current ferry schedule before buying tickets, pack water and layers, and keep track of the last return sailing. The Boston Public Library’s Central Library at Copley Square rewards a visit beyond the front steps. Look at the McKim building’s staircase, murals, courtyard and Bates Hall, remembering that readers are there to work. General admission is free. A self-guided look and a booked tour are different visits, so check the library’s tour calendar if you want a guide. The MIT Museum in Kendall Square is the Cambridge choice for science, technology and hands-on exhibits. If paintings and sculpture are more your interest, Harvard Art Museums in Harvard Square is another option, with free admission. Choose one for the afternoon rather than racing between both. They are in different squares, with different collections and admission policies. Quincy Market and Faneuil Hall are neighboring buildings with different roles. Browse the market if you want something to eat, then visit Faneuil Hall for its history as a meeting place. The National Park Service offers free talks in the Great Hall when it is available. City events can affect access. The marked Freedom Trail connects 16 historic sites over roughly two and a half miles, from Boston Common to Charlestown. You can follow it independently and stop where your interest takes you. Walking the route is free, but entry to some sites costs extra. Leave time to go inside a place or two instead of only photographing the signs. Make your Boston bucket list manageable Keep the waterfront stops together, pair Back Bay with the library and Newbury Street, and give the Fenway museums their own afternoon. Our free and cheap Boston guide covers admission discounts worth checking before you pay. For a ferry trip, choose the return boat before choosing lunch.
3 eateries open 24 hours in Boston
A discussion in the Secret Boston Facebook Group started this guide with a practical question: where can you eat at any hour? Bova’s Bakery, South Street Diner and the Brighton IHOP each advertise round-the-clock service. They also solve different problems. One is a takeout bakery; the other two give you somewhere to sit with a meal. These three eateries open 24 hours in Boston cover the North End, the Leather District and Brighton. Choose the neighborhood before you choose the pancakes. Crossing the city for food is a different proposition after midnight, especially if you have been counting on taking the T home. Bova’s Bakery is the stop for a North End pastry run that has got well beyond dessert time. The family bakery has been in business since 1926, and its own visitor information confirms 24-hour service every day of the year. At 134 Salem Street, you can pick up Italian baked goods without waiting for a breakfast opening. Make your plan a takeout one: Bova’s explicitly says it has no sit-down dining. That matters if you are hoping to bring a group inside, settle in with coffee and wait out the night. It accepts major credit and debit cards, so there is no need to make an extra trip to an ATM. Anyone with a food allergy should call before heading over; the bakery warns that its products are subject to cross-contact. The display case is an invitation to choose what is available, rather than a promise that a particular item will be waiting. South Street Diner gives you a proper diner at 178 Kneeland Street, near South Station. Its history and current service information describe a restaurant built in 1947 by the Worcester Dining Company to feed local factory workers. It was formerly known as the Blue Diner. The building has had rather more practice with odd eating hours than most of us. Choose it when you want to sit down instead of taking a bag of food outside. The diner posts its menu and online ordering links, which are the useful places to check before committing to a particular meal. Being near a station makes it convenient geographically, but it does not make trains run through the night. Check your onward service separately, and allow time to eat rather than treating a diner stop as something you can squeeze into a short connection. The IHOP at 1850 Soldiers Field Road in Brighton lists 24-hour opening on all seven days. Pancakes, omelets, waffles and burgers give a group room to disagree about whether this meal counts as dinner or breakfast. You do not have to settle that question before ordering. This is the Brighton branch specifically, so check the address before following a map result for another IHOP. The restaurant lists dine-in, takeout, online ordering and curbside pickup. Its own ordering page is a better place to compare the current menu and total than an old delivery screenshot. For someone already in Brighton, the location can spare a trip across town for an all-night meal. For someone in the North End, Bova’s is the much more local answer. Getting food at three in the morning Open all night does not mean every item is available all night. Before making a long trip for a particular pastry or meal, call the restaurant. Check holiday notices too, even at businesses with regular 24-hour service. A bakery counter is a better fit for something to carry home; a diner makes more sense if everyone needs a seat and a little time. For a delivery order, enter your actual address and inspect the estimated arrival time before choosing food. A restaurant being open does not guarantee a delivery driver is available. For a visit, check the trip home before leaving: do not assume a subway or commuter-rail service will still be running when you finish. If you are eating earlier in the night, our late-night food guide gives you more choices. Keep this shorter list for the hour when “serves late” is no longer late enough.
Get to know Boston
Bostonians are generous and loyal but it goes both ways
Outsiders might read the generosity as a performance on the way in and coldness on the way out. Wrong. It’s an account. Reciprocity is expected in this town. When you skip your turn you say something about you. The first round The bar is the easiest place to see this. Someone raised here, especially in the neighborhoods, will fight to get the first round. We will argue for the privilege because that’s how we show we like you, but if you don’t buy one back, it’s an insult. What, so you don’t like me? Or worse, you’re a cheap motherfucker. Most of us won’t say that, although some will say the last part, joking/not-joking. Either way, you’re on the outs. Irish pub culture has the same rule written more tightly. The Irish Times describes the round as a system, not an act of generosity. Mess it up and you can damage a reputation or a friendship. Irish Central is blunter: nobody reminds you when it is your turn, and people will talk. Bostonians are the same way with conversation. Only talk about yourself, never ask a question, and show no interest in the other person, and it’s over. We also have strict rules about family and friends. For neighborhood Bostonians, family is always right and the people we have known since kindergarten are family. In the schoolyard we backed them no matter what, and we still do. New friends are judged the same. Pass and you have a friend for life. Galway House is one of the oldest Irish bars in Boston. Photo by 4300streetcar Parish, neighborhood, round This culture is thickest in Irish Catholic working-class neighborhoods of Boston like Jamaica Plain, South Boston, Roslindale, and Dorchester, or JP, Southie, Rozzie, and Dot. People who leave those places tend to take the culture with them, and new people notice even if they can’t name what they are noticing. None of this came from nowhere. Rural Ireland ran on neighbor labor as well as kinship. A meitheal was a working party. Neighbors helped with a harvest or a turf cut, then expected the same help when their own work came due. The Irish Independent describes it as neighbors helping each other in turn, with no wages, on farms of roughly equal size so nobody cleaned up at everyone else’s expense. That is not a romantic clan from a movie. It is a practical rule: you show up, then they show up. Boston gave that rule a parish and a street. Irish Catholic immigrants built churches against real hostility. In Dorchester, a church under construction in Lower Mills burned in 1854, a fire many believed was set by Know-Nothings. St. Gregory’s followed. Later, people from the neighborhood still asked what parish you were from, because the parish was the map. Global Boston notes that Irish Americans left more slowly than some other groups in part because Catholic parishes could not pick up and follow them to the suburbs the way a synagogue could. A study of South Boston’s Irish enclave, drawing on Thomas O’Connor and on residents, put it in plainer language. People identified themselves by parish as much as by Irish county. In South Boston you learned silence and loyalty. Those are not opposite traits. They are the same system seen from two sides. You take care of your own. You do not advertise the terms. Call it clan if you want. The useful word is still the round. Help is supposed to come back and loyalty is supposed to be answered. Conversation is supposed to have a return. People who grew up in it think it’s normal, but people who didn’t think we’re a harsh bunch. They don’t realize our generosity is not charity, it’s membership. If you want in, buy the next drink, ask a question, and show up when it is your turn. If you don’t, you just won’t be asked back.
Why Bostonians say “wicked” so much
“Wicked good” is a compliment. “Wicked expensive” is a complaint. The same word does both jobs without any concern for whether the subject deserves praise. In Boston, “wicked” often means very or extremely. It turns up the volume on whatever comes next. Say someone is wicked tired and you mean they are very tired, not that they have become a worse person. The meaning comes from how the word is being used. That is the useful thing to know before attempting a Boston impression. You can pronounce every R and still use the word correctly. You can also drop every R and put “wicked” in a sentence where it sounds like you learned to speak from a souvenir sweatshirt. Why Bostonians say wicked before almost anything In this usage, “wicked” is an intensifier. Merriam-Webster records its adverbial meaning alongside the older adjective meaning morally bad. The two uses can occupy the same language without confusion. A wicked person and a wicked good sandwich are different propositions. Think of “wicked cold,” “wicked funny” or “wicked crowded.” The word strengthens the description. It does not tell you whether to like the thing being described. Someone saying the restaurant was wicked busy might be recommending it, explaining a long wait, or wishing they had stayed home. The placement is more important than putting on an accent. “That was wicked good” has the familiar local construction. “That was wicked,” meaning excellent, is another slang use, but it does a different grammatical job. Adding the word everywhere will not make every sentence sound more Boston. The Puritans do not get automatic credit Boston’s reputation makes an origin story involving stern Puritans tempting. But the fact that an old word existed in England does not prove that seventeenth-century settlers brought this particular local use with them. The language program A Way with Words discusses “wicked” as a New England intensifier. That regional association is useful. It does not supply the name of the first person who said it, or a neat date when everyone in Massachusetts agreed to start. There is no need to invent a founding ceremony. People repeat words they hear in their families and communities, and a familiar expression can feel entirely ordinary to one speaker and immediately regional to another. “Wicked” works perfectly well without a colonial certificate of authenticity. Ordering a frappe does not require dropping an R Other local words need a little more translation. A frappe is a thick milkshake; the familiar New England pronunciation rhymes with “cap.” The spelling can make visitors expect a different word, especially if they are thinking of a coffee drink. For an order, the menu is more useful than a debate over terminology. Ask what is in the drink if the distinction matters. Regional vocabulary is interesting until it becomes the reason you receive something other than the ice cream you wanted. “Bubbler” means a drinking fountain, with a history that reaches beyond Massachusetts. Our bubbler explainer separates the regional word from a frequently repeated manufacturing story. Calling it a water fountain is also a perfectly effective way to ask for water. Vocabulary is not the same as an accent The Boston accent concerns sounds: which R’s a speaker pronounces, what happens between words, and how vowels are formed. Vocabulary concerns the words chosen. They overlap in conversation, but one does not require the other. A person raised here might say “wicked” constantly, occasionally, or never. Another might arrive from elsewhere and pick it up. Neither case is a useful citizenship test. Boston contains more than one way of speaking, and ordinary conversation is less uniform than the movie version. If the word is new to you, listen to what follows it. Good, bad, fast, slow, cheap, expensive: the next word does the describing. “Wicked” just makes sure you heard.