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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
The boozy theory behind Jamaica Plain’s name
Jamaica Plain’s name may owe something to Jamaican rum, but nobody has established who chose it or why. Other theories credit a Massachusett leader or England’s capture of Jamaica from Spain. The rum explanation has enjoyed a long career without producing a receipt. The rum story has company The Caribbean explanation comes in more than one version. One credits Jamaica’s rum and its popularity among local drinkers. Another connects the name to England’s capture of the island from Spain in 1655. In a 2019 GBH interview about the name, historical society president Gretchen Grozier described the rum story against the setting of rural Roxbury, with inns and taverns along the road to Dedham, now Centre Street. The suggestion is that the drink’s association with the area became a nickname. The conquest explanation proposes a different motive: commemorating an English victory. Grozier identified it as a possibility, while emphasizing the weak connection between the military event and the neighborhood’s name. Neither explanation establishes that local sugar refineries named Jamaica Plain. A connection to Caribbean trade and a documented naming decision are different things. The trade itself also deserves more than a cheerful tavern anecdote. Boston College’s Global Boston history of Jamaica Plain connects the wealth of early estate-owning families to international commerce involving enslaved people, rum and other commodities. That economic history is substantial even where the etymology remains uncertain. The “plain” in Jamaica Plain’s name Before Jamaica Plain, there was Pond Plain. The Jamaica Plain Historical Society’s neighborhood guide identifies that earlier name with Jamaica Pond and the surrounding land. At the time, the area belonged to Roxbury. “Plain” described the relatively level ground around the pond and village, rather than promising that every future resident would have a flat walk home. The larger neighborhood includes hills. Boston University’s architectural and community history project describes an agricultural district of hills, farms and orchards in 1800, with wealthy Bostonians establishing estates beside the pond and Stony Brook. The older geographical label helps explain half the name. The difficulty is establishing how “Jamaica” became attached to it. A Massachusett leader is one possible namesake One longstanding explanation connects the name to Kuchamakin, a Massachusett sachem, or leader, whose name appears in several English spellings, including Cutshamekin. In Walter H. Marx’s account of the naming question, published in the Jamaica Plain Gazette in 1992 and preserved by the historical society, Kuchamakin’s association with the pond provides a possible route from a person’s name to a place-name. Under this explanation, English speakers altered his name into “Jamaica.” The different spellings reflect attempts to represent an Indigenous name in English. The explanation concerns a person associated with the area, rather than a literal translation of the modern neighborhood name. Marx also records a story about an Indigenous basket maker named Jamaco who lived beside the pond. Her story belongs among the accounts people have passed down, but the article does not establish it as the naming event. Why Jamaica Plain’s name still has competing explanations The sources do not give us a single person announcing a name and explaining the choice. Instead, they preserve different attempts to make sense of one that was already in use. A historian describing a tradition is useful evidence that the story circulated. It is not the same thing as a record of the original naming. The place itself has also changed. The neighborhood's pond, farmland and country estates belong to an earlier version of an area now connected to the rest of Boston by city streets and transit. Reading an old geographical label against the modern neighborhood can make it sound stranger than it did to the people using it. You can still start with the most visible piece of the explanation: Jamaica Pond. The earlier name Pond Plain located the community beside an actual body of water. Take the gardens and neighborhood walks at their own pace rather than treating the name as a puzzle that has to be solved before you get there. The rum story remains a possibility, and an unusually durable one. Nobody has produced the naming decision that would turn it into the answer. Jamaica Plain has managed to keep the name without agreeing on who deserves the credit.
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.