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 just about time to break out the ornaments, lights, wreaths, and garland. From over-the-top décor to holiday cocktails, from afternoon teas with guest appearances by Santa to hot cider at a giant market, 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 2024; 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: Not holiday-specific, just wonderfully wintery décor and specials (and some igloo dining!)
Holiday and Winter Beverage Pop-ups
From Santa-themed cocktails to luxurious hot chocolate
Hot chocolate at “Avery Bar Chocolat.” / Photo courtesy of the Ritz-Carlton, Boston
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 while choosing among decadent toppings—from egg nog choux pastry puff to caramel whipped cream—and indulging in pastries and sweets alongside the drink. Also, bring the kids: Adults can sip a richer cup (with the optional addition of a spirit or cordial) made of a blend of milk and dark chocolates, while the little ones enjoy a lighter, easier-drinking style. After, bring the kids to the lobby to write letters to Santa. Avery Bar Chocolat runs from 11 a.m. to 5 p.m. on Saturdays and Sundays through December 29; $39 for adults (excluding alcohol) and $19 for children. Reservations here (listed under “Experiences.”)
The Ritz-Carlton, Boston, 10 Avery St., Downtown Boston, 617-574-7100, ritzcarlton.com/boston.
Holiday Afternoon Tea in the Newbury Boston’s Garden Room
Tea sandwiches, scones, and holidays treats accompany J’enwey Teas, tea-based cocktails, and glasses of Champagne at the Back Bay hotel’s afternoon tea on December 21, 22, and 23 ($115/adult or $140 with a glass of Veuve Clicquot; $65/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.
Après Skate at Coterie at Four Seasons Hotel Boston. / Courtesy photo
Hot Chocolate, Cocktails, and Tea at the two Four Seasons
For the 2024 holiday season and stretching through to the end of March 2025, Four Seasons Hotel Boston (alongside the Public Garden) is debuting its new “Après Skate” experience at its lobby lounge, Coterie, featuring Manjari Grand Cru hot chocolate with house-made croissants and whipped cream, not to mention a full French-inspired food menu (beef bourguignon with truffles, poutine, and more). Stop by between 11 a.m. and 11:30 p.m. daily.
A mile away at the Four Seasons One Dalton Street, head to the cocktail lounge, Trifecta, to find Nutcracker-inspired seasonal beverages, including a boozy hot chocolate. Also at Trifecta, there’s a holiday-themed afternoon tea service Fridays, Saturdays, and Sundays in December, with treats including currant and cranberry white chocolate scones, eggnog parfait, and more, paired with seasonal teas and liqueurs. (Adults start at $99/person, with various add-ons, and a children’s menu is available at $49/kid.) Make an afternoon tea reservation here.
Four Seasons Hotel Boston, 200 Boylston St., Back Bay, Boston, 617-338-4400, fourseasons.com/boston; Four Seasons Hotel One Dalton, 1 Dalton St., Back Bay, Boston, 617-377-4888, fourseasons.com/onedalton.
The Inn at Hastings Park’s “Christmas Tea with Santa”
Lexington’s acclaimed Inn at Hastings Park offers a lovely Saturday high tea all year, but on December 14, 15, 21, and 22, it’s a special holiday edition for the whole family, including: tea, cocktails, 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.
Louis Roederer Holiday Champagne Bar at the Mandarin Oriental, Boston
For the holiday season, the Mandarin Oriental’s lobby is decked out in Christmas lights and other festive décor, including a large tree. The season’s events and offerings include live music by Berklee students and cozy space by the crackling fireplace, not to mention a pop-up Champagne bar featuring Louis Roederer selections by the bottle and glass, and in cocktails. A menu of caviar and light bar bites accompanies the drinks. The pop-up bar runs from 5 p.m. to 8 p.m. on December 6, 7, 13, 14, 20, 21, and 31.
Mandarin Oriental, Boston, 776 Boylston St., Back Bay, Boston, 617-535-8888, mandarinoriental.com.
A Maccabee bar cocktail. / Courtesy photo
Maccabee Bar
A vodka sour with jelly doughnut notes; an after-dinner dark rum sipper with chocolate gelt garnish; latkes aplenty—oy vey! Founded in 2018, Boston bar star Naomi Levy’s Hanukkah-themed cocktail bar is back this year, running from December 2 to January 1 at Noir in Harvard Square. (It’s open Monday through Saturday, plus Sunday, December 29, during Hanukkah.) In addition to the latkes, there’ll be other snacks coming out of Noir’s kitchen, including house-made sufganiyot (jelly doughnuts). Limited reservations available via email (noir@charleshotel.com) 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 late December for Miracle’s over-the-top décor and glassware, featuring silly but tasty drinks with names like Christmasaurus 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.
Special holiday season desserts at Santa’s Cantina at Loco Fenway. / Photo by Sarah Healy
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 succulents) and a special holiday cocktail menu with drinks such as the Griswold Family Tree, a pomegranate margarita served in an ornament. The dessert menu gets wintery too, with options such as red velvet skillet cookies topped with vanilla ice cream and Mexican chocolate sauce and a “choc-utterie board” with cookies, chocolate fondue, and more.
61 Brookline Ave., Fenway, Boston, 857-277-0769, locotacoshops.com.
Snowport. / Photo by Alexander Pickering
Snowport
The Seaport District’s annual holiday market is back for its sixth year, and in addition to a ton of vendors, Betty the Yeti sightings, iceless curling, 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); watch for options like hot mulled cider from Downeast Cider and a variety of other cocktails (some served hot). There’s plenty of food to go with those drinks, include melty cheese in a surprisingly high number of forms.
Snowport, 100 Seaport Blvd., Seaport District, Boston, bostonseaport.xyz/snowport.
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 2024 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, a stuffed elf, 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.
Whiskey Wonderland at Short Path Distillery
The Everett distillery has turned its new Barrelhouse Bar into a cozy holiday hideaway with festive vibes, whiskey tastes, and cocktail flights, open on December 6, 13, 20, and 27; reservations encouraged. (The space is available for group rentals up to 30 on other days of the week.) Also on the calendar: Wintery Mix, a party on December 14 that will involve absinthe fountains, spiked hot chocolate, pierogi, and other fun; and Old Fashioned Night on December 20.
71 Kelvin St., Everett, shortpathdistillery.com.
Good Holiday Vibes
These venues really deck the halls
Delux Cafe
This casual 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, food and drink specials, and events including Santa visits and live holiday music, both on December 14 and 21.
100 High St., Downtown Boston, highstreetplace.com.
The upside-down tree display at the Liberty Hotel. / Courtesy photo
The Liberty Hotel
Is it really December 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 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 spiced glazed ham or molten chocolate cake.
Fairmont Copley Plaza, 138 St. James Ave., Back Bay, Boston, 617-585-7222, oaklongbarkitchen.com.
Publico Winter Market
Publico is changing things up from its usual après ski winter décor this year, instead 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 late December—or perhaps a little later—and is family-friendly. On Saturday December 7, 14, and 21, Santa will be onsite for a brunch buffet (and photos, of course)—reservations are required (see “Experiences” at the bottom of this page).
11 Dorchester St., South Boston, 617-622-5700, publicoboston.com.
Candy Cane Forest (pistachio liqueur, mint, and cherry), a 2024 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 decorated its cocktail bar for the season. (Here’s a peek inside.) It’ll last through the end of January if you don’t have time to get in during the holiday rush. Drinks such as the coquito-like Yuletide Snack and wintery snacks like baked brie with jam 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, installed in partnership with local florist Beach Plum Floral Design. 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. Reservations strongly encouraged.
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 family, is now “the Winsorbread House” through New Year’s Day, decorated with plenty of ornaments, tinsel, and more. Watch for drink specials like boozy white chocolate egg nog, a gingerbread 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 from late November through late 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
Not holiday-specific, just 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 third 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. A special food and drink menu will be available after 5 p.m. daily, plus a special weekend brunch, with winter-themed cocktails, hot cocoa, and plenty of comfort food, including sweet and savory fondues.
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, spicy tuna 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 “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.
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. 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—and consider selecting the chocolate fondue add-on.
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 previously hosted Wicked Haunt Fest has transformed into a winter wonderland with ice skating, shopping, food and drink, an après ski-inspired lounge area, and more. Some of it is Christmas-y, including weekend meet-and-greets with Santa and a life-sized gingerbread house, but the fest will remain open through January 25 for general winter whimsy. Food options include fried Oreos, Buffalo mac and cheese, clam chowder, egg nog-stuffed croissants, and more, plus beer, wine, and seasonal drinks, like hot chocolate and gingerbread lattes. Entry and three hours of parking are free; find more info here.
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.”
