The Ultimate Holiday Guide to Eating, Drinking, and Merrymaking in Boston
Where to find the best holiday cocktail pop-ups, hot chocolate bars, Santa teas, highly decorated restaurants, and ski-lodge-inspired winter patios in and around the city.
“Rudolph’s Replacement,” a Miracle pop-up cocktail. / Photo by Melissa Hom
With winter on the horizon and stores already dusting off their Christmas playlists, it’s clearly the season for holiday festivities. What does this mean in the Greater Boston hospitality scene? For many restaurants, bars, and hotels, it’s time to break out the ornaments, lights, wreaths, and garland. From over-the-top décor to holiday cocktails, from breakfast buffets with guest appearances by Santa to hot cocoa by hotel lobby fireplaces, there’s a lot going on these days.
Below, we’re tracking holiday beverage pop-ups (cocktails, hot chocolate, tea, etc.); venues that get really decked out for the holidays; and ski-lodge-inspired winter pop-ups and other cold-weather activations that’ll keep that festive feeling going into the new year. (You may also be interested in our guides to holiday lunches, cozy fireplaces, and hot chocolate.)
This guide was most recently updated in December 2025; keep an eye out for periodic updates.
Jump to:
- Holiday and Winter Beverage Pop-ups: From Santa-themed cocktails to luxurious hot chocolate
- Good Holiday Vibes: These venues really deck the halls
- Winter Wonderlands: Wonderfully wintery décor and specials (and some igloo dining!)
Holiday and Winter Beverage Pop-ups
From Santa-themed cocktails to luxurious hot chocolate
Avery Bar Chocolat 2025. / Courtesy photo
Avery Bar Chocolat
On weekends throughout the holiday season, the Ritz-Carlton’s swanky Avery Bar—complete with a cozy marble fireplace!—becomes the ultimate hot chocolate destination. Relax over a warming mug topped with vanilla marshmallows or whipped cream, and indulge in sweets from a chocolate buffet, including brownies, chocolate-dipped strawberries, and more. Also, bring the family: Adults can sip a richer cup (with the optional addition of a spirit or cordial) or try a chocolate-infused cocktail while the little ones enjoy a lighter, easier-drinking style of cocoa. After, bring the kids to the lobby to write letters to Santa. Avery Bar Chocolat runs from 11 a.m. to 3 p.m. on Saturdays and 11 a.m. to 5 p.m. Sundays from November 29 through December 28; $49 for adults (excluding alcohol) and $24 for children. Reservations here (listed under “Experiences.”)
The Ritz-Carlton, Boston, 10 Avery St., Downtown Boston, 617-574-7100, ritzcarlton.com/boston.
Christmas Tea with Santa at the Inn at Hasting Park’s Town Meeting Bistro
Lexington’s acclaimed Inn at Hastings Park offers a lovely Saturday high tea all year in its restaurant, Town Meeting Bistro, but on December 13, 14, 15, 20, and 21, it’s a special holiday edition for the whole family. Included: tea, a cocktail, and towers of sweet and savory bites for the grownups; tea or hot cocoa, snacks, and activities for the kids; and, of course, pictures with Santa for everyone. Reserve via Resy (see the “Upcoming Events” section at the bottom). $90/adult; $65/child 3-12.
Town Meeting Bistro at the Inn at Hastings Park, 2027 Massachusetts Ave., Lexington, 781-301-6655, innathastingspark.com.
Cocktails, Holiday Décor, and Labubu Hot Pot at Royal
This Korean barbecue and sushi spot in Quincy has a flair for dramatic presentation year-round, but swing by during the holiday season for even more drama. Christmas decorations abound, and the restaurant is featuring a holiday cocktail menu with concoctions such as a “snowball martini” and Grinch punch. Also, there’s…Labubu hot pot? Sure, why not?
227 Parkingway, Quincy, 617-481-4874, royalquincy.com.
Drinking Chocolate and Whiskies Galore at the Four Seasons One Dalton
Head to the hotel’s cocktail lounge, Trifecta, to find the holiday-season “Whisky Omakase” experience at a six-seat bar from November 29 to January 1. The tasting of rare House of Suntory whiskies and bourbons includes small bites that complement the spirits, from smoked local oysters to smoked duck breast crostini. $249 per person; book here (under “Experiences”). Plus, the hotel lobby chocolate bar returns this year, featuring L.A. Burdick drinking chocolate and confections. Swing by daily between noon and 8 p.m. from December 1 through January 2.
Four Seasons Hotel One Dalton, 1 Dalton St., Back Bay, Boston, 617-377-4888, fourseasons.com/onedalton.
The Greatest Winter Wonderland at the Greatest Bar
The multistory West End bar is hosting a pop-up with Tinseltown and Nutcracker-themed décor, holiday food and drink specials, and tons of events, including holiday movie brunches, a wreath-making workshop, and more. A portion of proceeds will support the Greater Boston Food Bank. Programming runs from late November through late December.
262 Friend St., West End, Boston, 617-367-0544, thegreatestbar.com.
Afternoon tea at the Newbury Boston. / Courtesy photo
Holiday Afternoon Tea at the Newbury Boston
Make way for holiday cheer at the Newbury Boston’s holiday afternoon tea, featuring a Make Way for Ducklings tea set. Tea sandwiches, scones, and holidays treats accompany J’enwey teas and glasses of Champagne at the Back Bay hotel’s afternoon tea at 3:30 p.m. on December 20 through 23 ($120/adult or $145 with a glass of Taittinger Champagne; $70/child). $5 per reservation will go to the Highgate Charitable Foundation, supporting children’s health. Book here.
The Newbury Boston, 1 Newbury St., Back Bay, Boston, 617-536-5700, thenewburyboston.com.
The Jingle Bar at PKL
Southie’s PKL, home of pickleball and barbecue, is hosting the Jingle Bar this year, a holiday-themed cocktail pop-up with seasonal locations around the United States and Canada. From an all-Christmas-all-the-time soundtrack to over-the-top décor, plus prizes for the best Christmas-themed outfits and other entertainment, it’s sure to be a festive time. It runs from December 4 through 23—and don’t miss Wednesday nights, featuring singalong carols. Tickets here. (21+ except for select Saturday afternoon sessions.)
64 C St., South Boston, thejinglebars.com.
A Maccabee bar cocktail. / Courtesy photo
Maccabee Bar at Noir
A vodka sour with jelly doughnut notes; a rum-and-sweet-potato concoction mixing Moroccan and tropical inspirations; latkes aplenty—oy vey! Founded in 2018, Boston bar star Naomi Levy’s Hanukkah-themed cocktail bar is back this year, running daily through the month of December, including on Christmas, at Noir in Harvard Square. Because it’s Maccabee Bar’s eighth year, and eight is a special number in the story of Hanukkah, expect extra-special additions—trivia, prix fixe dinners, and some surprises along the way. In addition to the latkes, there’ll be other snacks coming out of Noir’s kitchen, including house-made sufganiyot (jelly doughnuts). Reservations available but plenty of space for walk-ins.
Noir (the Charles Hotel), 1 Bennett St., Harvard Square, Cambridge, 617-661-8010, maccabeebar.com.
Shore Leave, decorated for the annual Sippin’ Santa pop-up. / Photo by Reagan Byrne
Miracle and Sippin’ Santa
Christmas-themed cocktail pop-up Miracle and its Christmas-meets-tropical spinoff, Sippin’ Santa, are taking up residence at several Boston-area venues yet again this year in a fun, kitschy tradition that got its start in New York City in 2014. The pop-ups have since franchised out around the world, with Boston-area bars participating since 2017. Head to the Hotel Marlowe in Cambridge, Mystic Station in Malden, and the Goat in Newburyport from late November through early January (dates vary by location) for Miracle’s over-the-top décor and glassware, featuring silly but tasty drinks with names like Christmapolitan and Snowball Old Fashioned. Sippin’ Santa, meanwhile, returns to Shore Leave in Boston’s South End to delight with the rummy Sugar Plum Mai Tai and lots more. Check each venue’s website for detailed information on dates, times, and other important info.
Multiple locations, miraclepopup.com and sippinsantapopup.com.
Nutcracker-Themed Bar at the Mandarin Oriental, Boston
For the holiday season (November 17 through New Year’s Day), the Mandarin Oriental’s lobby is decked out in Nutcracker-inspired décor, including a large Christmas tree. (There’s a fireplace, too!) Find a Nutcracker-themed bar with cocktails, Champagne, and small plates, plus live music, throughout the season.
Mandarin Oriental, Boston, 776 Boylston St., Back Bay, Boston, 617-535-8888, mandarinoriental.com.
The Naughty List Lounge at the 88 Club. / Courtesy photo
Naughty List Lounge at Kings
Kings locations in Burlington and Lynnfield and the 88 Club inside Kings Back Bay have transformed into the Naughty List Lounge through the end of December (nightly in Burlington and Lynnfield; Thursday through Sunday at the 88 Club). There’s no cover, and there are photo ops aplenty with festive decor, plus bowling and games in Burlington and Lynnfield and live music in Back Bay. The special cocktail list includes a peppermint spin on an espresso martini, Fireball and Rumchata shots dubbed “Reindeer Games,” and more.
Kings, 510 Market St., Lynnfield; 52 Second Ave., Burlington; playatkings.com; the 88 Club, 50 Dalton St., Back Bay, Boston, 88club.boston.
Santa’s Cantina at Loco Fenway
Loco Taqueria & Oyster Bar has turned its enormous Fenway location into a winter wonderland full of themed décor, dubbed Santa’s Cantina. Swing by in December to enjoy the ambiance (including 1,500 giant ornaments and a Christmas tree made of wine bottles) and a special holiday cocktail menu with drinks such as the Naughty List, a vodka, creme de cassis, and rosemary cocktail served in an ornament. The dessert menu gets wintery too, with options such as the Cantina Snowman, a cheesecake-flavored cake-pop dipped in white chocolate.
61 Brookline Ave., Fenway, Boston, 857-277-0769, locotacoshops.com.
A winter cocktail at Sugar Factory. / Courtesy photo
Sugar Factory’s Over-the-Top Holiday Drink Specials
This chain is basically built for social media, with Instagrammable décor and drinks year-round. For the 2025 holiday season, Sugar Factory dials it up even more with a Santa’s Wonderland theme. Drinks include garnishes such as a marshmallow snowman lounging under a cocktail umbrella and a chocolate Santa, and there’s even a mini Christmas tree that arrives packed with four holiday martinis. There’s themed food, too, from sliders on green and red buns to blue pancakes topped with wintery embellishments.
101 South Market St. (Faneuil Hall Marketplace), Downtown Boston, 857-317-4793, sugarfactory.com.
Park 9 Dog Bar’s Christmas setup. / Photo by Tracey Crosby
Whoville at Park-9 Dog Bar
Sip on themed cocktails like the Cindy Lou Who (vodka, yuzu, honey, lemon, ginger beer) among holiday décor from December 1 through Christmas—while chilling with adorable dogs, of course.
48 Waters Ave. #1, Everett, 617-294-8048, park9dogbar.com.
Snowport. / Photo by Alexander Pickering
Winter-Themed Bars at Snowport
The Seaport District’s annual holiday market is back for its seventh year, and in addition to a ton of vendors, Betty the Yeti sightings, and other fun, there are numerous opportunities to drink wintery beverages. The setup includes four holiday-themed bar areas (Jingle Bar, Dizzy Dreidel, and more) with winter- and holiday-inspired drinks. There’s plenty of food to go with those libations, including melty cheese in a surprisingly high number of forms.
Snowport, 100 Seaport Blvd., Seaport District, Boston, bostonseaport.xyz/snowport.
Good Holiday Vibes
These venues really deck the halls
Delux Cafe
This casual, cash-only South End haunt always looks like December with its year-round Christmas lights and convivial vibe. Swing by the eclectic spot for a warm dive-bar feel, $6 cans of Schlitz, and comfort food. (We’re big fans of the bathroom, too.)
100 Chandler St., South End, Boston, 617-338-5258, thedelux.com.
Grill 23 & Bar always decks the halls. / Courtesy photo
Grill 23 & Bar
The 40-plus-year-old steakhouse always looks grand for Christmas: think wreaths, a big tree, and other elegant touches. Check out the special holiday lunch on select dates in December, or make a reservation for a fancy steak dinner anytime. We also whole-heartedly recommend a post-work visit to the bar for a drink and dessert (like the signature coconut cake or classic chocolate chip cookies).
161 Berkeley St., Back Bay, Boston, 617-542-2255, grill23.com.
High Street Place
The Best of Boston food hall is celebrating the season with festive photo ops (with a Wicked spin) throughout late November and December, plus Santa visits and other holiday fun on December 13 and 20.
100 High St., Downtown Boston, highstreetplace.com.
Lansdowne Lodge at the Lansdowne Pub
Catch live music Thursdays through Saturdays through January 4 amid holiday decor, complete with upside down Christmas trees, fake snow falling during performances, and other cheer. No cover or reservations needed unless you want to decorate a gingerbread house while you’re there (available on Thursdays from 6 to 9 p.m.) Keep an eye out for themed cocktail specials, too.
9 Lansdowne St., Fenway, Boston, landsdownepubboston.com.
The upside-down tree display at the Liberty Hotel. / Courtesy photo
The Liberty Hotel
Is it really the holiday season if you haven’t gazed up in awe at the Liberty Hotel’s upside-down Christmas tree display in its tall atrium? It’s a good opportunity to plan a visit to one of the hotel’s restaurants or bars, including Lydia Shire’s Italian-inspired mainstay, Scampo.
215 Charles St., Beacon Hill, Boston, 617-224-4000, libertyhotel.com.
On your way to Oak Long Bar + Kitchen, you might spot Cori Copley, the Fairmont Copley’s “canine ambassador,” pictured here in front of the hotel’s tree in 2022. / Photo by Kataram Studios
Oak Long Bar + Kitchen
Luxurious Back Bay hotel Fairmont Copley Plaza really does it up come Christmastime: You’ll typically see items like a giant Christmas tree and an array of dazzling festive wreaths. The vibes spill into the hotel’s gorgeous restaurant, Oak Long Bar + Kitchen—which is open on Christmas Day, in case you’re looking to feast on a 50-ounce Tomahawk steak for two or sticky toffee pudding.
Fairmont Copley Plaza, 138 St. James Ave., Back Bay, Boston, 617-585-7222, oaklongbarkitchen.com.
Publico Winter Market
Publico is once again transforming its courtyard into the Publico Winter Market, full of winter greenery (including a 16-foot Christmas tree) and festive food and drink specials for lunch, dinner, and weekend brunch. It’ll last through the end of December and is family-friendly. On December 6, 13, and 20, Santa will be onsite for a breakfast buffet (and photos, of course)—reservations are required.
11 Dorchester St., South Boston, 617-622-5700, publicoboston.com.
Rebel’s Holiday Room at the Revere Hotel
Rebel’s Guild’s private dining room is decorated for the holidays, with themed tables available for $15 (reservations required). The decorations will stay up through January 4, with tables available between 4 and 10 p.m. nightly. Be sure to try one of the seasonal cocktails, like a cinnamon-and-smoke Old Fashioned or a spiked hot cider, and comforting cold-weather fare like chowder or papardelle Bolognese.
200 Stuart St., Downtown Boston, reverehotel.com.
Candy Cane Forest (pistachio liqueur, mint, and cherry), a holiday season cocktail special at Stratus at View Boston. / Photo by Derrick Zellman
Stratus at View Boston
White Christmas trees, twinkling lights, fun cocktail specials, and skyline views 51 stories up: Inside the Prudential Center, the View Boston observatory has again decorated its cocktail bar for the season. (Here’s a peek inside last year’s setup.) The so-called Winter Oasis will last through February, helpful if you don’t have time to get in during the holiday rush. Drinks such as the coquito-like Yuletide Snack and snacks like caviar deviled eggs accompany the stunning views.
Stratus at View Boston, the Shops at the Prudential Center, 800 Boylston St., Back Bay, Boston, viewboston.com/stratus.
Holiday decorations at the Venetian in Weymouth. / Photo by Paige Harding/PAH Photography
The Venetian
Head south of the city to dine among over thousands of ornaments and twinkling lights, not to mention garlands, trees, and other Christmas-y magic. The spacious Italian restaurant has completely transformed into a holiday wonderland—and it’ll remain that way through the end of January, in case you want to keep the Christmas feelings going post-December. (Try a three-course holiday lunch on November weekends or any day in December.) Reservations strongly encouraged, but bar space and some tables are reserved for walk-ins.
909 Broad St., Weymouth, venetian-weymouth.com.
The Winsorbread House. / Photo by Emily Hagen
The Winsorbread House at Island Creek Oysters
Duxbury seafood restaurant the Winsor House, part of the Island Creek Oysters family, is now “the Winsorbread House” through New Year’s Day, decorated with plenty of ornaments, tinsel, and more. Watch for drink specials like a peppermint espresso martini, a banana bread Old Fashioned, and, for the kids, toasted Fluff hot cocoa and “Grinch punch,” tropical juices and lemon-lime soda with a Pop Rocks rim. Reservations encouraged.
390 Washington St., Duxbury, 781-934-0991, winsorhouse.islandcreekoysters.com.
Wusong Road
Every inch of this tiki bar and restaurant is filled with eye-catching décor year-round. Visit in December, though, and you’ll find even more: “Wusong Wonderland,” as the team calls it, returns this year with plenty of Christmas-y accents, seasonal tiki mugs, and other surprises.
112 Mt. Auburn St., Harvard Square, Cambridge, 617-528-9125, wusongroad.com.
Winter Wonderlands
Wonderfully wintery décor and specials (and some igloo dining!)
Après… @ Deck 12. / Courtesy photo
Après… @ Deck 12
Who says rooftops are just for summer? For the fourth year, Yotel is turning its popular indoor-outdoor roof deck into the mountain lodge of your ski-themed dreams: heated gondola-like spaces, Adirondack chairs, and such—not to mention stunning Boston skyline views. Chili flights and fondues help keep diners warm.
Yotel Boston, 65 Seaport Blvd., Seaport District, Boston, 617-377-4747, deck12bos.com.
Yurts at the Bowery Bar in Lower Mills. / Courtesy photo
Bowery Bar Yurts
The Dorchester restaurant’s three private, heated yurts are back for the season, available for lunch, dinner, and weekend brunch bookings (reservations required) of groups up to eight. Bowery Bar serves a comfort food-filled menu of dishes like Thai chili wings, blackened fish tacos, loaded nachos, burgers, and cookie skillets.
2261 Dorchester Ave., Lower Mills, Dorchester, Boston, 617-698-2261, bowery-bar.com.
“Inngloos” at the Inn at Hastings Park. / Photo by Paige Harding/PAH Photography
The Inn at Hastings Park’s “Inngloos”
This boutique hotel’s igloos—sorry, inngloos—are warmed by a faux-fireplace heater, and with blankets and hand warmers available, each igloo seats up to six for a private lunch, brunch, dinner, or tea, featuring menus from the inn’s Town Meeting Bistro. Think dishes such as seared Arctic char with saffron coconut quinoa, braised lamb neck with harissa couscous, and hanger steak with chimichurri. Children can be accommodated, as can dietary restrictions. Book online or by phone; a $120 fee is required when the reservation is made. The so-called INNgloo Wonderland is set up from November through April.
2027 Massachusetts Ave., Lexington, 781-301-6655, innathastingspark.com.
Matria Terrace S’mores
At the Intercontinental, Italian steakhouse Matria is offering s’mores kits by the fire on its waterfront terrace this holiday season, limited availability nightly. Grab two or three friends and toast some marshmallows alongside Fort Point Channel.
510 Atlantic Ave., Downtown Boston, 617-747-1000, ihg.com.
A rooftop igloo at the Mercantile. / Courtesy photo
The Mercantile Rooftop Igloos
Finding yourself in the Worcester area this winter? Head to the Mercantile for rooftop igloos with city views. The heated dining spaces come equipped with Bluetooth speakers, and you can enjoy the full dinner and cocktail menu. (The restaurant describes its food as “New American tavern cuisine”—think brick-oven pizzas, hearty salad and rice bowls, sandwiches, and comfort-food entrees like mac and cheese and steak tips.) Reserve via OpenTable.
2 Mercantile St., Worcester, 774-389-5180, themercantileworcester.com.
Igloos at the Lookout Rooftop at the Seaport’s Envoy Hotel. / Courtesy photo
Rooftop at the Envoy Igloos
In the Seaport, the Envoy Hotel’s rooftop is adorned with various options for outdoor winter revelry: igloos, enclosed “iceboxes,” fire pits, and curling rinks. Drinks and light snacks are available at each, plus skyline views. Check the website for pricing and capacity details. 21+ after 4 p.m.
70 Sleeper St. (Envoy Hotel), Seaport District, Boston, 617-338-3030, theenvoyhotel.com.
Winter Fest. / Courtesy photo
Winter Fest at Hood Park
A two-acre plot of land in Charlestown that has been hosting seasonal festivals for the past couple years is again home to Winter Fest, taking place on the evenings of December 6-7, 12-14, and 19-30 (closed on Christmas Eve and Day). The space has been transformed into a winter wonderland with ski gondolas, light installations, a local artisan market, hot cocoa aplenty, and a ferris wheel. Food options include fried Oreos, Buffalo mac and cheese, and more. Admission is $5.
100 Hood Park Dr., Charlestown, Boston, winterfestboston.com.
Portions of this guide appeared in the print edition of the December 2023/January 2024 issue with the headline “It’s the Most Wonderful Lunch of the Year.”
