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Guides
9 Boston holiday guides for what to do, where to go and what to buy
Boston once banned Christmas. From 1659 to 1681, taking the day off or throwing a Christmas feast could cost you five shillings. Now the city’s holiday lightings start the Saturday before Thanksgiving, and the plans pile up from there. Every Secret Boston holiday guide is right here, plus our own shop, sorted into what to do, where to go and what to buy, with a line on what’s inside each one. Start with the lightings if you have kids, the party spots if you’re planning the office party, and the gift guide if you’re shopping for someone who loves Boston. Our Boston holiday lightings guide has all six, from Sat, Nov 21 through Thu, Dec 3, including the night Santa arrives by boat at Martin’s Park and the Boston Common tree that Nova Scotia sends every year. Boston has 6 Nutcrackers this December, with ballet, burlesque, big band jazz and one in French, and every show runs between Fri, Nov 27 and Thu, Dec 31. Our A Christmas Carol guide starts at the hotel where Dickens first read it to Americans, then sends you to the Muppets singing it and a 1795 tavern for a toast to Scrooge. Hanukkah in Boston runs Fri, Dec 4 to Sat, Dec 12, with a Hanukkah day at the MFA, menorahs on Hummer limos in Brighton and where to get your latkes. Mariah Carey’s holiday bar makes its Boston debut in the Seaport on Wed, Nov 25, and our pop-up guide has six more Christmas bars, with which ones take walk-ins and which are 21+. These 9 holiday party spots build the office party around a game, with axe throwing, skeeball, darts and dueling pianos, and room for 10 people or a few hundred. Our Snowport guide explains how the Seaport’s holiday market works, plus the curling, Betty the pink yeti and what to check before you go. Our Boston gift guide has gifts we designed ourselves, starting at $16, plus a gift membership we email on the day you choose. Our shop’s Boston Ugly Christmas Collection starts with the Boston Ugly Christmas hoodie, from $52 in navy, with knit-style snowflakes and trees, BOSTON across the chest and the CITGO sign worked into the pattern. The same design comes on a crewneck, a tee, a beanie, a pom-pom hat, an ornament and wrapping paper. Our Wicked Good Christmas Collection puts “Have yourself a Wicked Good Christmas” on a hoodie, a tee, a beanie and an ornament. Free shipping on orders over $50. Order by Saturday, Dec 5 to get it in time for Christmas. The Boston craft fairs guide has 20 markets, Snowport, SoWa and Harvard Square included, in date order through Christmas.
5 ways to find free food and drink in Boston
Free food in Boston usually comes with a small amount of homework. You might need a rewards account, a birthday in the right week or a place in line on one particular day. A free tasting is also a tasting, so do not arrive expecting dinner. These five options spell out those differences. Some are available through local shops, others through chains with Boston locations. They include a birthday credit that may not cover your whole order and an annual giveaway whose next date has not been announced. Knowing that beforehand is better than finding out at the register. Panera’s current MyPanera terms include a free individual bakery treat for the basic membership tier, with no purchase required. Add your birthday to your account, then look for the reward when it arrives. It must be selected when you order; it will not simply apply itself. The reward lasts seven days after it is loaded. Eligible treats include items such as a cookie, muffin or bagel, subject to the price limit in your offer. Spreads and several other categories are excluded, and modifications can cost extra. Higher membership tiers have different birthday benefits, so read the reward you actually receive. Use a participating café rather than ordering through a third-party delivery service. Flour’s rewards program lists $5 in Flour Dough on the first day of your birthday month, available to use before the month ends. That gives you more breathing room than a benefit redeemable only on your birthday. Set up your account ahead of time and check that the credit has appeared before ordering. It is a dollar credit rather than an unrestricted free sandwich or pastry. If your total exceeds it, you pay the difference. Look at the current prices and your account’s redemption instructions before deciding what to get. The point is to use a benefit you have, not to turn a five-dollar credit into an excuse for a much larger order. Formaggio Kitchen’s South End shop advertises free Friday wine tastings from 4 to 6 p.m. for adults over 21. It is a chance to try what the shop is pouring and ask questions without buying a ticket to a formal class. Bring identification and confirm that week’s session before heading over. Read the event listing carefully because Formaggio also offers paid tastings and classes. The recurring Friday tasting does not make everything on the calendar free. Treat it as a brief stop to learn about a few wines, rather than a substitute for a bar tab. If you do find a bottle you want to buy, that purchase is separate. Starbucks’ birthday reward covers one eligible drink or food item at a participating store. You must join Rewards at least seven days before your birthday, provide the date and make at least one Star-earning transaction before your birthday each year. That purchase requirement matters: this is a benefit for qualifying customers, not a no-spend sign-up giveaway. Green members redeem on their birthday. Gold members have seven days starting that day, and Reserve members have 30. Check your level and the reward in the app. The offer excludes items such as packaged coffee and food or drinks intended for several people. One birthday does not qualify an entire office for coffee. Ben & Jerry’s holds an annual Free Cone Day, but the official event page currently marks the 2026 event as finished and invites sign-ups for news about 2027. Do not use an old April date as a reason to queue outside a scoop shop now. When the next announcement appears, check which local shops are participating and the event hours. This one belongs on a future reminder, not today’s lunch plan. There is also no need to guess the date from previous years: the organizer will publish it. Go because you want a scoop, with enough time to spare for the line. Keep the free part free Before ordering, open the actual reward and check its expiry, eligible items and participating locations. Choose pickup or an in-person redemption when possible: delivery charges can turn a complimentary cookie into a surprisingly expensive cookie. Do not add something you do not want just to qualify for a promotion. Signing up also means sharing information with a business. Use the programs you will actually remember to check, and skip the rest. A birthday treat is pleasant; a phone full of restaurant notifications is a less convincing present. For a tasting or annual giveaway, confirm the specific Boston location before making the trip.
Get to know Boston
4 Boston-area gangster hangouts with brutal backstories
The Winter Hill Gang once conducted business in a Somerville garage that now welcomes a church congregation. On Prince Street, Mafia associates talked inside an apartment while the FBI recorded them. In South Boston, a couple opened a liquor store and soon found themselves being told to hand it over by men threatening to kill them. Boston mob headquarters were a first-floor apartment on Prince Street, a liquor store on Old Colony Avenue whose owners kept saying no, and two garages, one later filmed by state police and one now used as a church. The North End headquarters with microphones in the walls 98 Prince Street, North End Gennaro Angiulo and his associates used a first-floor apartment at 98 Prince Street as a Mafia headquarters. From January 19 to May 3, 1981, the FBI recorded the conversations through hidden microphones, and a concealed camera outside photographed people coming and going so the voices on the tapes had faces. Those recordings became evidence in federal court. An FBI supervisory special agent later told the Senate that one slice of the Angiulo family's numbers business was bringing in $30,000 a day. For nearly a year before those tapes, the FBI could not get video of the address. People nearby reported suspected investigators to the Angiulos, often with a license plate, and they were usually right. Across 103 days of pictures, someone brought the brothers a new car or a new face on nearly every day. Agents hid a camera in a vehicle and changed that vehicle every evening. They were not spotted. The liquor store Whitey Bulger refused to take no for 295 Old Colony Avenue, South Boston Stephen Rakes and Julie Rakes opened Stippo's Liquor Mart in 1983. Julie later used the name Julie Rakes Dammers. In January 1984, James "Whitey" Bulger, Stephen Flemmi, and Kevin Weeks let themselves into the family's South Boston home. Bulger said they had been paid to kill Rakes and had decided to buy the store instead. Rakes said it was not for sale. Bulger said he would be their partner. Rakes refused that, too. They were back that evening. They sat at the kitchen table, showed a gun and a switchblade, and threatened to kill him. Flemmi picked up the couple's one-year-old daughter, stroked her hair, and said it would be a shame for her not to see her father again. Bulger handed Rakes a paper bag with roughly $65,000 and promised $25,000 more, which he later refused to pay. Flemmi said the store had new owners. The First Circuit's account of the extortion lays out that visit. The Rakeses held out for weeks, left for Florida, and came back still trying to keep the business. Julie's uncle, Boston police detective Joseph Lundbohm, asked FBI agent John Connolly for help. Connolly told Bulger. Bulger then told Rakes to make Lundbohm back off, and the family signed the title over. The store was at 295 Old Colony Avenue. Public records show Kevin Weeks bought the property. In May 1986 the building was sold to Weeks, Bulger, and another person, and South Boston Liquor Mart, Inc. was set up to do business there. The shop was also known as Columbia Wine and Spirits and by its original name, Stippo's Liquor Mart. A federal forfeiture appeal is where the address and the 1986 company are traced. The garage where the afternoon visitors weren't coming for repairs Lancaster Street, near the former Boston Garden Mechanics had the Lancaster Street Garage in the morning. Most days around 1:30 p.m., Bulger and Flemmi arrived, Bulger in a black 1979 Chevy that he pulled into a bay, and the visitors came for them rather than for a repair. Dick Lehr and Gerard O'Neill describe that routine in Black Mass. George Kaufman, who had operated Marshall Motors in Somerville as a front for Howie Winter, ran this garage for the two of them. They had moved the meetings downtown, a short walk from 98 Prince Street and a couple of blocks from Boston Garden. Massachusetts State Police filmed Bulger there in 1980. The Justice Department still has the footage. The Winter Hill headquarters that became a church 12 Marshall Street, Somerville Marshall Motors, at 12 Marshall Street in Somerville, was the garage they left behind. Kaufman ran it as a front for Howie Winter, and the back room is where Winter, John Martorano, and Bulger met. The Boston Globe described the place as the Winter Hill Gang's office for gambling and loansharking. James Sousa was killed there in October 1974, after other gangsters worried he would talk to police about a botched plan to rip off a dentist with a fake gold sale. A mobster, remembering the room years later, said, "There was blood everywhere." A church bought the building in 2008. In May 2026 the Globe found it open as Greater Works Church of God Somerville. Reporter Danny McDonald went to a Sunday service and found purple seats, screens welcoming worshippers, and a mural of people being baptized in a river. Rev. Collin Green led the prayers. After the service he brought up Howie Winter on his own. "It's changed," he said. "It's not that way. God is in the building."
The famous Boston accent and its obsession with the letter R
Say “car,” then say “car engine.” For someone with a traditional Boston accent, the R can disappear in the first version and return in the second. The next sound makes a difference. That detail gets lost in plenty of Boston impressions. Removing every R gets you only so far, and eventually gets you somewhere nobody here is from. The accent has patterns involving consonants, vowels, and the way words meet in a sentence. It also varies considerably among the people who use it. Which R’s does the Boston accent drop? Linguists call the traditional accent non-rhotic. In ordinary terms, speakers often leave out an R after a vowel when another consonant or a pause follows. Think of “park,” “card,” or “car” said on its own. The R at the beginning of “red” stays. So does the one in “bring.” A Boston speaker is not applying a blanket ban to the letter. An R can also return at the end of a word when the next word starts with a vowel sound. In “car engine,” the words connect through the R. This is called linking R, a pattern also found in other non-rhotic English accents. Try saying the phrases naturally rather than giving each word its own pause. The difference is easier to hear in a sentence than in a list of words written with “ah” at the end. And where do the extra R’s come from? Then there is intrusive R: an R sound between words where no R appears in the spelling. “The idea of it” can sound like “the idear of it.” The vowel at the beginning of “of” creates the setting for that extra sound. It does not mean every Boston speaker says “idear” whenever the word appears. The University of York’s explanation of linking and intrusive R describes how one pattern developed from the other. Speakers extended an existing way of joining vowel sounds to words that did not have a written R. The extra consonant helps two vowel sounds meet. It follows a pattern, rather than arriving wherever an actor decides to put it. The vowels matter, too Listen to “cot” and “caught.” For many traditional Boston speakers, those words sound alike. That shared vowel is another important part of the accent, although it receives considerably less attention than “pahk.” Some speakers also use a broad A in words such as “bath” or “half,” bringing the vowel closer to the one in “father.” These features are not a checklist every Bostonian completes. A person can have a recognizable local accent without using all of them. You can hear examples in WBUR’s recordings and explanation of Boston speech, which includes Dartmouth linguist James Stanford discussing the sounds. Listening is more useful than trying to reconstruct an accent from exaggerated spelling. How Boston came to sound this way Boston speech belongs to the broader Eastern New England dialect region. Its history includes the English spoken by early settlers and the region’s continuing connections with England. Boston University linguist Neil Myler points to settlers from East Anglia as an important influence on the region’s R-dropping speech. Stanford also emphasizes the close contact Boston maintained with southeastern England, where non-rhotic pronunciation gained social prestige. That history helps explain the connection, but the accent has continued changing here. The way someone speaks also reflects their family, community, education, and social surroundings. Four centuries of Boston life did not leave the original dialect untouched. “Wicked” and “frappe” are a different part of the story An accent concerns pronunciation. A dialect includes vocabulary and grammar as well. “Wicked,” used to mean very or extremely, is vocabulary. In “wicked cold,” it increases the force of “cold.” It does the same job in “wicked expensive,” with less pleasant financial implications. “Frappe” is another regional word, pronounced “frap” in the familiar local usage. Merriam-Webster records both that pronunciation and the thick-milkshake meaning. Someone can order a frappe, complain that it is wicked expensive, and pronounce every R. Knowing the words and having the accent are separate things. Not everyone raised here sounds the same Research has documented differences across age groups and communities. In a 2010 study of Boston and two New Hampshire towns, linguists Naomi Nagy and Patricia Irwin found that younger speakers pronounced more post-vocalic R’s than older speakers. Education and other social factors also mattered. Those results concern the people in the study, rather than every younger person in Boston. They also measure one feature: someone who pronounces more R’s can retain other local sounds. The accent does not disappear the moment one pronunciation changes. For some people, sounding local is a source of pride. Others have felt pressure to soften their pronunciation to avoid being judged. Both experiences help explain why a city can have such a recognizable accent without all its residents sharing it. Pronouncing the R in “Dorchester” does not cancel out having grown up there.