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Guides
Best pumpkin patches in the Boston area
A pumpkin trip can be a quick stop for something to carve or an afternoon involving a wagon ride, apple picking and several doughnuts. Before choosing among pumpkin patches in the Boston area, decide which version you want. The activities, admission arrangements and distance from the city vary considerably. These four farms are in Harvard, Tyngsboro, North Andover and Northborough. They are day trips out of Boston, and their pumpkin offerings are seasonal. Check the farm’s daily update before leaving, particularly after rain. A farm store can be open while its fields or wagon rides are closed. Westward Orchards takes visitors to its pumpkin patch by wagon on fall weekends. Its 2026 schedule runs from September 19 through October 18, with rides from 11 a.m. to 4 p.m. Rain stops the wagon, so this is one to check again on the morning of your visit. The farm also sells pumpkins, gourds and seasonal decorations around the store, which gives you an alternative if you only want to shop. Add apple picking while the orchard is open, or buy apples, cider doughnuts and produce inside. Pumpkin-patch rides and the store have different hours; an open shop does not mean the wagon is still running. Parlee grows its pumpkins on the farm, then moves them into a display patch for visitors to choose from. You are selecting a harvested pumpkin rather than cutting one from a vine. That distinction is useful if the field-picking experience is the whole reason for your trip. There is enough else here to fill an afternoon: apple picking in season, cider doughnuts, warm apple crisp and Annie’s Animal Barns. The farm’s daily news page lists what is open, picking deadlines and food service. Its regular fall schedule closes the farm on Mondays. Activity hours can end before the farmstand closes, so do the patch first if you arrive later in the day. Smolak’s fall weekends combine choosing a pumpkin with activities such as hayrides, animal feeding and the Cow Train. This is the option for a family that wants more than one stop after parking. The farmstand and bakery give you somewhere to pick up food before heading home. Read the fall festival details for your date before paying. Activities can be bought separately or in packages, and the packages do not automatically include everything on the farm. Compare the listed contents with what your children will actually do. Apple picking, flowers and food have their own arrangements. Tougas stocks its patch with carving pumpkins, decorative varieties, smaller pumpkins and gourds. Ask staff which are suitable for cooking if you want one for the kitchen as well as the front steps. The farm sells pumpkins by weight with a minimum charge, so a bigger pumpkin also means a bigger bill. Use the picking and pricing page to compare pumpkin-patch hours with the orchard and farm kitchen. They are not interchangeable. Apple picking has a separate purchase and admission arrangement, while the barnyard, playground and cider doughnuts give families other reasons to stay. Check conditions before setting off; fields can close when supplies or weather change. Choosing between pumpkin patches in the Boston area For a wagon ride to the patch, look at Westward’s weekend schedule. For pumpkins plus animals and food, compare Parlee and Tougas. Smolak is the choice here for a day built around several children’s activities, with the costs checked individually before you buy a package. Wear shoes that can handle soil and damp grass. Leave pets at home unless the farm explicitly permits them; Westward, Parlee and Tougas publish restrictions. If a member of your group needs a step-free route, ask specifically about the patch, wagon boarding and toilets. Farm-store access does not tell you whether the field will work. For a closer-to-home afternoon on another day, our free and cheap Boston outings include parks and indoor options. Save the farm trip for a day when you have time to stay.
A free Oktoberfest in Southie, then Halloweentown
Castle Island Brewing pours a free Oktoberfest in Southie on the 17th. Friday is a scare in the Seaport, with pumpkin painting on Newbury later in the month. Play It By Fear is the night for a costume without a ticketed maze. It is Friday, October 16, from 6:00 to 8:00 p.m. at The Rocks at Harbor Way, 111 Harbor Way. The Seaport’s own listing has candlelight caricatures, a tarot table, and a photo booth. DJ Brian Halligan starts at 6:00 p.m. JAM’N 94.5 host Ashlee Feldman is the host. At 7:00 the Glass Artists string quartet plays Halloween classics and themes from slasher films, an hour after the DJ starts. A stand will be scooping $1 ice cream, and Union Square Donuts and The Sweetish Fish are on site. Seaport VIP Insider deals that night run from 5:00 to 9:00 p.m. The list includes Flight Club, Levain Bakery, and Puttshack, along with other Seaport businesses. The page does not list a ticket price, so check before you treat the caricature as free. Castle Island Brewing’s Oktoberfest is Saturday, October 17, from 11:00 a.m. to 8:00 p.m. at 10 Old Colony Ave in South Boston. It is free, and you have to be 21. The day is German lagers, a make-your-own pretzel necklace, hot beer poking, and oompah music from Kier Byrnes. The listing asks for lederhosen and dirndls. Date Faster’s Halloween singles mixer is Saturday, October 17, from 7:00 to 9:00 p.m. It is 21 and over, and there are no timed dates. The page lists name tags, hosts, drink specials, and a game of Two Truths and a Lie. The prize is a ticket to another Date Faster mixer. Drinks are bought at the venue and are not included. Costumes are encouraged. Ticket totals run from $9.30 to $23.17. You can ask for a refund up to 7 days before the event, or exchange the ticket for another date. The calendar lists Howl at the Moon, 184 High Street. The description on the same event also says the venue is to be announced. Read the ticket page the day you go, and do not plan the night around the pianos at Howl at the Moon until that line is gone. The Boston Public Market Association’s Harvest Party is Thursday, October 22, from 5:30 to 7:30 p.m. at Boston Public Market, 100 Hanover Street. The market closes at 3:00 p.m. that day for the party. Tickets cover unlimited tastings from market vendors, local beer, wine, and spirits, plus live entertainment and a silent auction. Individual tickets are sold through Zeffy, so the nonprofit keeps the full price. Sponsorships and in-kind gifts are open too. Boston Landing screens Halloweentown indoors on Saturday, October 24, at the TRACK at New Balance, 91 Guest Street. Admission is free and an RSVP is required. The pre-party is at 3:30 p.m. and the screening is at 5:30 p.m. It is all ages. The page linked here lists 3:30 to 8:00 p.m. The Eventbrite listing ends at 7:00 p.m. This entry uses 3:30 to 8:00 p.m. Refunds can be requested up to 7 days before the event. PruBoo is a free family Halloween event on Sunday, October 25, from 11:00 a.m. to 1:00 p.m. at the Prudential Center, 800 Boylston Street. Kids trick-or-treat at more than 30 stores and restaurants. The page also lists face painting, Halloween crafts while supplies last, magic shows by Robert Clarke at 11:30 a.m. and 12:30 p.m., and The Stacey Peasley Band. A trick-or-treat bag is a $5 donation to Boston Children’s Hospital. The band is listed from 10:30 to 11:30 a.m. and from noon to 1:00 p.m. The 10:30 start is before the stated 11:00 a.m. start. Sonsie hosts pumpkin painting on Monday, October 26, from 6:30 to 8:30 p.m. in the downstairs Wine Room at 327 Newbury Street. The ticket is $44.52 and includes a pumpkin, paints, a welcome mocktail, and light bites, and you take the pumpkin home. Food at Sonsie is 20 percent off before or after the event if you stay to eat. Refunds are available until seven days before the night. The location is still a secret. Experience Halloween Night 1 is a costume rave on Friday, October 30, from 9:00 p.m. to 2:00 a.m., and the venue is listed only as TBA. Experience and Techno Brooklyn are hosting. Briela Veneno, Crossbow, and L9 play. Costumes are encouraged. It is 21 and over, and tickets are listed from $25. Ned Devine’s Halloween party is Saturday, October 31, from 8:00 p.m. to 2:00 a.m. at 1 Faneuil Hall Marketplace. There is a DJ and a costume contest. First prize is $300 and the runner-up prize is $200. Guests have to be in the door by 10:00 p.m. It is 21 and over with a valid ID. Angry Orchard is the sponsor. Sales are final. The poster says advance tickets are $10. Eventbrite’s total is $11.54. Trixie’s Halloween is a 21-and-over dance party on Saturday, October 31, at Royale, 279 Tremont Street. Doors are at 9:00 p.m. Tara Dikhof opens, Trixie Mattel DJs, and the night includes pop-up performances from Boston drag performers plus a $1,000 costume contest hosted by Trixie. Katya is not performing. Presented by Royale Boston. Ticket sales are final. A promo code, DISCO, is $5 off. It does not apply to every show. Send us a message if you have an event you want added. Visit our Holidays events page for more.
Get to know Boston
Why happy hour in Boston is still banned
A bar can knock a few dollars off your oysters at five o’clock. Your martini is another matter. Happy hour in Boston is still restricted by a Massachusetts regulation that prohibits temporary drink discounts, free drinks and promotions built around drinking more for less. The rules apply across the state. Cambridge and Somerville cannot offer an escape route, and calling a promotion an industry night does not create one. As of September 19, 2026, the legislature is still considering a change. A Senate vote in favor of happy hour is not the same as permission for your local bartender to start pouring two-for-one margaritas. Why happy hour in Boston disappeared One of the events behind the ban happened outside the Ground Round in Braintree on September 9, 1983. Kathleen “Kathy” Barry, a 20-year-old woman from Weymouth, died after riding on the hood of a car driven by a friend who had been drinking at the restaurant. Some of the driver’s beers had been prizes in a music trivia contest. Reporting based on interviews with Barry’s family and former state officials describes how her death helped turn alcohol promotions into a public-safety issue. Her parents pressed for stronger measures against drunken driving. Massachusetts introduced the restrictions in 1984, during Michael Dukakis’s administration. They targeted the offers that could encourage someone to drink quickly or keep ordering: free rounds, discounted drinks and contests with alcohol as the reward. The ban dates to the same period as many of the clubs in our look at Boston’s bars of the 1980s. The rules have outlasted quite a few of the rooms. An all-day special is not a loophole The key phrase in the regulation is “same calendar week.” A bar cannot offer a drink for less than its regular price during that week. Selling a margarita for $8 all Tuesday and $12 on Wednesday does not get around that restriction merely because the Tuesday price lasted longer than an hour. A reasonably priced drink is allowed. A temporary discount on that drink is what creates the problem. Those are different things when you are comparing menus, even if both might leave you with a smaller bill. The regulation also prohibits charging a selected person or group less than the general public that day, with an exception for private functions not open to the public. Being a restaurant worker, a regular or the person celebrating a birthday does not, by itself, create an exemption. Bottomless brunch has a problem too The restrictions cover unlimited drinks sold for a fixed price during a set period. That rules out the usual public bottomless-mimosa promotion. Increasing the amount of alcohol without a proportionate price increase is prohibited as well, so a bigger pour is not a substitute for a discount. There are limits on service alongside the pricing rules. A licensee cannot deliver more than two drinks to one person at once. Pitchers of beer or mixed drinks must be served to at least two people. Drinking games and contests that award drinks are prohibited. Some provisions make exceptions for private functions. Buying a ticket does not necessarily make an event private; a publicly advertised offer still needs to comply with the rules. Food specials are a different story The regulation’s exceptions expressly allow free food and entertainment, as well as a drink included in a meal package. A discounted appetizer or oyster offer can therefore be legitimate even when its advertised time sounds like happy hour. Read what the offer actually includes. A food discount does not necessarily mean a cheap evening once drinks, tax and tip arrive. And a meal package is not blanket permission for unlimited cocktails alongside a plate of fries. For an evening built around the room and the drinks rather than a promotion, our Boston speakeasies guide is a useful place to start. The latest attempt to change the rules In July 2026, the Senate passed economic-development legislation containing a local-option proposal for discounted drinks. It would allow participating cities and towns to authorize time-limited discounts, subject to conditions including advance notice and a 10 p.m. cutoff. At this article’s September 19 check, the official bill history still showed House and Senate conference committees appointed on July 30 to resolve their differences. The proposal had not become law. Until that changes, a free birthday drink from the bar remains prohibited. Your friends, however, can buy the round.
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.