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Things to Do in Boston This Weekend

October 30–November 1, 2026

Halloween lands on Saturday this year! Operation Mincemeat plays its last Boston shows this weekend, the Boston Symphony Orchestra premieres a piece written to play alongside a live AI system, and Downtown Crossing puts dogs in costume on Saturday afternoon.

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12 viral Halloween costumes that are so 2026

Show up as a broken AI image, six fingers and the tell-tale extra hand. Or what about a World Cup jersey (or the duck who never got in). Of course, there's always the Storrowed truck, which you know everyone gets. Beacon Hill is where a bad costume goes to die. Last year the city shut Mount Vernon, Pinckney, and a pile of other streets from 4 to 7:30 p.m. so the trick-or-treat crowd could take them over. The Beacon Hill Times ran the list. Brick, cobblestones, and someone asking what you are. Miranda has already rejected your costume. Silver hair, huge sunglasses, a coat that looks like rent. Andy is tall boots and a good coat. Emily is allowed to insult both of you, and someone has to carry the coats all night. The Devil Wears Prada 2 put Meryl Streep, Anne Hathaway, Emily Blunt, and Stanley Tucci back together, and it is on Hulu and Disney+. It made about $693 million, so people will know who you are. A cape on the Green Line. Matt Damon is Odysseus, Anne Hathaway is Penelope, Zendaya is Athena, and Charlize Theron is Calypso. Circe is Samantha Morton. Do not show up as Circe and then argue. Linen, leather, gold, and sandals you can walk in. Odysseus gets the sword. Athena gets the helmet. Calypso gets to look dangerous. Couples can be Odysseus and Penelope. Ten years apart is optional. The movie has already passed $1.7 billion. Extra hand. Six fingers. A shirt with letters that almost spell words. A name tag that says Regenerate. The worse it looks, the clearer it is. One shoe should be a different size. An arm can come out of the wrong place. Bring a framed photo of yourself that does not look like you. You can start this at 6 p.m. and still be right. Diamond bones down to your fingers, a feathered coat, and a crown that will not survive the bar. Beyoncé wore it to the Met Gala in May, her first time back in a decade. Vogue has the arrival, Olivier Rousteing dress included. A black or nude bodysuit and silver bones will get you there. Rhinestones if you are patient. The coat is what keeps it from looking like last October. A hockey jersey will not get a second look in Boston. The name on it has to. Briar University, from Prime Video’s Off Campus. Jersey, stick, athletic shorts. The specific versions are better. Allie’s Shakespeare look is a blue corset, a satin dress, and fairy wings. The couple is Hannah’s bunny and Garrett’s magician, not Allie’s. Teen Vogue laid those out. Cowboy boots, flared jeans, big hair, a western shirt, and something that says Choosin’ Texas. Without the words, you are dressed for a country bar. Ella Langley’s song spent 23 weeks at No. 1, the longest run in Hot 100 history. A couple can split it. One person chooses Texas. The other one looks left. The costume people will understand is a national team jersey, a scarf, and a tiny trophy. Gillette hosted seven World Cup matches, including a quarterfinal, under the name Boston Stadium. CBS Boston has the list. Couples wear rival teams. The costume people will stop for is Merlín, the duck in a miniature Mexico jersey. Reuters followed him to a meeting with the president. He was still a duck. He did not get into the stadium. Stage clothes, the hair, the weapons. One of them works. All three work better. KPop Demon Hunters was already Netflix’s biggest movie, and Netflix ordered a sequel. Official HUNTR/X costumes exist, which beats building the whole thing out of metallic fabric after midnight. Woody, Jessie, and Buzz are the easy version. Lilypad is the one that dates it. She is the tablet in Toy Story 5, voiced by Greta Lee. Build a frame, put your face in it, and spend the night interrupting people. Disney said the opening was the biggest global debut of the year. Moana needs the necklace. Maui needs the hook, the skirt, the wig, and tattoos that were printed. A friend with a marker, after drinks, is not a plan. Catherine Lagaʻaia plays Moana. Dwayne Johnson is Maui again. The live-action movie opened July 10. It is a duo. Moana still does most of the work. Peach’s skirt has to be a problem on the T. Pink dress, crown, white gloves. Mario is overalls, a red cap, and a mustache. Rosalina makes it a group. A cardboard pipe makes every doorway a fight. The Super Mario Galaxy Movie put them back in theaters this year, so the closet version looks current again. Build a moving truck out of cardboard, crush the roof, and write Storrow Drive on the side. It reads as Boston from across the street, and it will take up a Beacon Hill sidewalk. Trucks keep hitting the low bridges on Storrow Drive, Soldiers Field Road, and Memorial Drive. The state calls it Storrowing.

Haunted places in Boston

Boston has been accumulating dead people since 1630, so the ghost stories had time to pile up. The places are real, ghosts, possibly. Harvey D. Parker opened the hotel in 1855. The hotel has published the ghost stories. In a 1992 Boston Globe interview quoted by the hotel, bellman John Brehm said he first heard about Parker’s ghost when he started work in 1941. The story then was that Parker roamed the 10th-floor annex. Around 1950, a guest said she saw a heavyset man with a black mustache in that hall. Security went up and found nobody. Other reports from that floor are a rocking chair in a room that does not have one, and lights moving down the corridor. In a separate story, a mother and daughter in room 1012 said a man in old clothes stood at the foot of the bed and then vanished. At breakfast, his portrait was hanging in the dining room. The granite building beside Massachusetts General Hospital was the Charles Street Jail, finished in 1851. In 1973, after prisoners revolted over the conditions, a court found the jail in violation of the inmates’ constitutional rights. The last prisoners left on Memorial Day weekend in 1990. It reopened as The Liberty Hotel in 2007. The rotunda, the catwalks, and some of the cells are still there. CLINK. serves dinner in the old cells. Alibi is in the former drunk tank. Ghost tours describe footsteps and former prisoners. The hotel’s own history does not. The theater opened in 1903. The stories that get repeated are a well-dressed couple in the balcony, a little girl who supposedly takes gifts left for her, and a former mayor who died in his seat during a performance. There is no record of a Boston mayor dying at the Majestic. People who have worked in the building still describe a man in a suit in the balcony lobby, and a child’s voice in the house. The restaurant opened in 1826, in a building that was already old. During the Revolution the second floor was headquarters for Ebenezer Hancock, paymaster of the Continental Army, and soldiers were paid where people now eat. Staff have talked about flickering lights, electronics that quit, footsteps, and a man in colonial clothes bent over a desk. Tour guides say that man is Hancock. A separate story involves a chef named Henry, seen by a coworker around the time Henry died. John F. Kennedy’s booth is upstairs, with a plaque. Ghost tours add a Kennedy haunting. The restaurant’s history page mentions the booth and stops there. Photo by Robert Linsdell King’s Chapel Burying Ground opened in 1630. It is the oldest burying ground in Boston proper. It filled up, and in 1660 the town opened the Granary Burying Ground nearby. Paul Revere, Samuel Adams, John Hancock, and the Boston Massacre victims are there, along with thousands of people who no longer have a stone. Both grounds are regular stops on ghost tours. Visitors report footsteps, cold spots, and someone in colonial clothes who is not leading a tour. The sightings are not verified. Fort Warren is on Georges Island in Boston Harbor. Construction ran from 1833 to 1861, and during the Civil War the fort held Confederate prisoners. The ghost story is the Lady in Black. In the version Boston Harbor Islands tells, she is Melanie Lanier, who rowed to the island to free her husband Andrew, a Confederate prisoner, and was hanged in black. Historians have not found a record of her. Edward Rowe Snow is the one who spread the tale. Georges Island is a ferry ride. Check whether the boats are running before you go.

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Whitey Bulger forced a family to sell him this Southie liquor store

Stephen and Julie Rakes had only recently opened their South Boston liquor store when James “Whitey” Bulger decided he wanted it. They told him it wasn’t for sale. He and his associates threatened the family until they surrendered the business. The address is 295 Old Colony Avenue, where Rotary Liquors appears in Boston’s licensing records today. Before that name, it was associated with Stippo’s Liquor Mart and the South Boston Liquor Mart, a business that became part of Bulger’s criminal operation. The story behind Whitey Bulger’s liquor store involves more than a gangster meeting place. It also involves a family who sought police help and an FBI agent who passed information to the man threatening them. The liquor store the owners didn’t want to sell Stephen Rakes and his then-wife, Julie, opened Stippo’s Liquor Mart in 1983. In January 1984, Bulger, Stephen Flemmi and Kevin Weeks went to the Rakes home to acquire it. The federal appeals court’s account of the takeover describes Rakes refusing both a sale and an unwanted partnership. Bulger responded with a death threat. The men returned later that evening with weapons. Flemmi picked up the couple’s young daughter while threatening her father’s life. Bulger handed Rakes roughly $65,000 and promised another $25,000. The gangsters treated that payment as making them the owners, despite the family’s refusal to sell. The pressure continued afterward. The family briefly fled to Florida, then returned and tried to hold on to the store. They eventually signed it over. The request for help that reached Bulger Julie’s uncle, Joseph Lundbohm, was a Boston police detective. When the couple asked for help, he approached FBI agent John Connolly. Connolly was handling Bulger and Flemmi as informants. The information Lundbohm brought him should have prompted an investigation into the threats. Instead, the federal court’s findings in United States v. Salemme describe Connolly failing to record the report or alert his supervisor, then telling Bulger about it. Bulger subsequently pressured Rakes to have Lundbohm back off. The family’s attempt to obtain protection had reached the person they needed protection from. That detail explains why this address matters beyond its association with Bulger. The store’s takeover was also an example of the protection his corrupt relationship with an FBI agent afforded him. The court found that the FBI did not investigate the extortion of the Rakes family. Before the liquor store, there was a garage Bulger and Flemmi had previously conducted business at the Lancaster Street Garage, 131 Lancaster Street, in Boston’s West End. The West End Museum’s history of the garage describes bookmakers delivering payments there after Bulger’s rise within the Winter Hill Gang. George Kaufman owned the business, officially called Lancaster Foreign Motors. Massachusetts State Police bugged the building in 1980 and watched its visitors from across the street. Bulger and Flemmi learned that the location was under surveillance and stopped using it for a time. The garage and the liquor store were different addresses serving a similar purpose: functioning businesses that also provided places for the gang’s activities. The sale agreement appeared at Bulger’s trial Decades later, the liquor store appeared among the exhibits introduced at Bulger’s 2013 trial. GBH’s collection of trial evidence identifies an agreement selling the South Boston Liquor Mart to Kevin Weeks, with Bulger named as a silent partner. It also identifies the business as Stippo’s. That document connects the names readers encounter in accounts of the property. Stippo’s and South Boston Liquor Mart refer to the business involved in the takeover, while the agreement placed Weeks in the transaction and identified Bulger’s interest behind him. What is at 295 Old Colony Avenue today? A Boston Licensing Board notice for May 2026 lists Rotary Liquors at 295 Old Colony Avenue, South Boston, operated by Mahabali Corporation. The notice concerns a request to change the manager of its retail alcohol license. The current business has a different name from the store described in the historical records. Its presence at the address should not be taken to suggest any connection between its present operators and Bulger’s crimes. For other addresses connected to Boston’s organized-crime history, our article on 4 Boston-area gangster hangouts covers the North End and Somerville locations separately.

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Order a milkshake in Boston and you might be missing the ice cream

Order a milkshake in Boston at a shop that still keeps the old distinction and you can get exactly what you asked for: milk and flavoring, beaten until it foams. No ice cream. The thicker drink, the one visitors usually mean, is a frappe. Not every counter still bothers. Plenty of menus now use milkshake the way the rest of the country does. The shops that list both drinks are not offering two sizes of the same thing. Those are the last places where a milkshake in Boston and a frappe are different orders. What goes into a milkshake in Boston The traditional local milkshake is milk plus a flavoring, often chocolate syrup, shaken or blended until air gets into it. A frappe adds ice cream. Yankee’s account of the two drinks is useful on a point people skip: the milkshake is not a glass of chocolate milk. Stirring syrup into milk mixes the ingredients. Blending them is what makes it a fountain order. If a menu lists both, look at the prices before treating the cheaper one as a deal. You may be comparing a milk drink with one that has scoops in it. Say “frap” The regional drink is one syllable, rhyming with map. The American Heritage Dictionary records that pronunciation and treats the noun as regional usage, mapping it to Rhode Island and southeastern Massachusetts. Shops in Boston still put it on the board. That entry is a different word from “frappé,” two syllables, which the same dictionary defines as a frozen fruit dessert or a drink poured over shaved ice. The spelling overlap is how visitors end up performing French at a Jamaica Plain counter. A shop owner paid for the lesson Vincent Petryk, who later opened JP Licks, learned the difference as a newcomer from Philadelphia. Boston.com reported that he ordered a milkshake at Bailey’s in the 1970s, saw that it cost half as much as the frappe, and then asked where the ice cream was. Bailey’s is gone. The mix-up is not. The same report found “frappe” in late-nineteenth-century Boston Globe pages attached to chilled and partly frozen drinks, including alcoholic ones, long before it settled on the ice-cream version. Recipes a few years later included cafe frappes and pineapple frappes, sometimes with a scoop of ice cream already in the mix. Boston University food scholars told the paper that regional names for ordinary foods were common before national food media flattened the vocabulary. Megan Elias, who directs BU’s gastronomy program, pointed to a 1920s overlap: Prohibition pushed people toward new places to sit, and electric equipment made ice cream cheaper to produce in volume. Soda fountains did well in that gap. The scholars also said the exact reason this particular word stuck here is not established. There is no inventor to toast and no afternoon when Boston renamed the milkshake. The term showed up in more than one drink, attached itself to the ice-cream one, and stayed. The word is still on the menu JP Licks still lists a regular frappe, an extra-thick frappe, and an espresso frappe, separate from smoothies, frozen coffee, ice-cream sodas, and floats. Extra-thick is a texture, not a citizenship test. In 2023, Mark Parrish, president of Crescent Ridge Dairy in Sharon, told Boston.com his shop still served the ice-cream-free milkshake next to the frappe and asked customers which they wanted. He also said tourists, students, and younger customers increasingly ask for a milkshake. Other counters have given up and will put ice cream in whatever you called it. Rhode Island complicates the map again. In parts of that state, and into southeastern Massachusetts, the ice-cream drink is a cabinet. Same general idea. Different word. This is the same class of local vocabulary as why Bostonians say “wicked.” Get the word wrong and you can still have a conversation. Get this one wrong and you may drink a glass of flavored milk. If the menu says milkshake and you want ice cream in it, ask. You do not need to win the regional argument first.

Boston’s streets make absolutely no sense

Take a wrong turn in downtown Boston and the city seems to rearrange itself behind you. A street bends without warning, changes its name, feeds into something called a square, and sends you back toward the place you just left. The usual explanation is that Boston paved over cow paths. It is repeated so often that it sounds like established history. The better explanation involves a small peninsula, private property, enormous amounts of fill and several towns that became Boston after laying out streets of their own. Boston’s streets started on a much smaller piece of land When English colonists established Boston in 1630, the Shawmut Peninsula was connected to the mainland by a narrow strip called Boston Neck. The route across it roughly followed present-day Washington Street toward Roxbury. There wasn't much room to leave town. The National Park Service describes the original peninsula as a place of three prominent hills, wetlands and estuaries. This was Massachusett land long before English settlement. Much of the ground that now seems inseparable from downtown Boston was still water. Early streets connected the places colonists needed to reach: houses, meetinghouses, markets, docks and fresh water. Routes fitted around slopes, shorelines and property. What served a small port town did not anticipate delivery trucks or someone trying to make a left turn on the way to a parking garage. The cows had other things to do Cows and sheep really did graze on Boston Common. The city eventually banned grazing there in 1830. That history explains why livestock belongs in the story, but it doesn't establish that wandering cattle determined the street plan. Ralph Waldo Emerson helped the idea stick. As Boston.com recounts in its examination of the cow-path story, he wrote, “we say the cows laid out Boston.” The article's historians point instead to fresh water, property boundaries and the original terrain as practical reasons for the early routes. A path used by animals might also have been used by people. That possibility is a long way from explaining an entire city. The cow story survives because it is easier to remember than the history of somebody else's property line. Boston made more land and gave it different streets Boston spent centuries creating room to grow. Hills were cut down, tidal areas were filled and the shoreline moved outward. The Leventhal Map & Education Center's account of landmaking describes both the physical work and the financial incentive: new ground could become valuable property. The result is particularly easy to see in Back Bay. Its rectangular blocks look different from the older streets downtown because they came from a different process. Planners could set out a street system for land being created, rather than fit roads around an existing waterfront town. Arthur Gilman produced his Back Bay plan in 1856. Filling began the following year and continued for almost four decades, according to the Friends of the Public Garden's history of Commonwealth Avenue Mall. The broad central mall gave the new neighborhood a long, planted space between its roadways. Arlington, Berkeley, Clarendon, Dartmouth, Exeter, Fairfield, Gloucester and Hereford streets even proceed alphabetically. Commonwealth Avenue, Newbury Street and Boylston Street run alongside one another. For a few blocks, Boston gives you a system you can remember. Boston also bought into other towns' street maps Today's city includes communities that developed separately. The city's annexation timeline records Roxbury joining in 1868 and Dorchester in 1870. Charlestown, Brighton and West Roxbury followed in 1874. Hyde Park joined in 1912. Those places already had roads, town centers and property boundaries. Becoming part of Boston did not erase them or require their streets to meet a Back Bay grid. A trip across the city can take you through several different systems without a sign announcing the change. Later traffic rules added another complication. One-way streets and turn restrictions can make a short route on foot a much longer trip behind the wheel. Knowing where a place is and knowing how to drive there are separate accomplishments. To see the difference without dealing with either problem, start on foot in Back Bay. Follow its rectangular blocks, then cross toward Beacon Hill's older, narrower streets. The change in the map is right under your shoes.

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.

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