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what to do in Boston this weekend (dec 20 - 22)

last minute shopping and heavy holiday vibes

Table of Contents

P.S. If you have an event, new attraction, new hotel, or restaurant opening you’d like me to cover, don’t hesitate to reach out.

food + travel news

So much happens every day that keeping up with the news can be challenging. Here are the headlines travelers need to be aware of this week.

around Boston

Cambridge-favorite La Saison has just expanded to Charlestown (221 Main St). Check out this Instagram-worthy space and pick up a loaf of sourdough bread, fresh croissants, chocolate cake, and more.

Kelly Walsh, one of the masterminds behind Sweet Cheeks, Tiger Mama, and other local favorites, just opened Russ & Mimi’s (16 Birch St), a new neighborhood market in Roslindale named after Walsh’s parentsStop in for sandwiches and other prepared foods to grab and go. They also sell wine, snacks (from near and far), produce, and more. 

The MBTA is consolidating some of the stops on the Green Line as part of its efforts to make the C branch fully ADA accessible. As first reported by StreetsBlogMASS, the plans include eliminating Kent Street and consolidating Brandon Hall and Fairbanks stops. 

travel news

A new FTC rule requires hotels and resorts to display any added-on “junk fees” in their rooms and short-term vacation rentals. According to a press release, this is supposed to help eliminate “bait-and-switch” pricing and the surprise of “resort fees” on hotel bills, not by doing away with the fees but by making sure you are aware of what you’re signing up to pay before you get to the check-in desk.

abroad

If you plan to visit the Greek Islands during your cruise in 2025, you will need to pay a little more to stop in Santorini and Mykonos. As Afar reports, the Greek government passed a resolution for a summer peak season levy (about 20 euros or $21 USD) to help curb overtourism and reinvest in the infrastructure of these popular destinations.

Traveling to China with a U.S. passport just got easier. If your trip is 10 days or less, you no longer need to apply for a visa to visit the country.

unique things to do in Boston: dec 20 - 22

holiday performances this weekend

This is the last weekend to see Charles Dickens's A Christmas Carol at Emerson College’s Emerson Cutler Majestic Theatre (219 Tremont St). Performances run through Dec 22. Tickets start at $10.

If you’ve missed (or can’t get enough of) Handel’s Messiah, Drunk Opera History is putting on its own performance of Drunk Opera History: Messiah Edition on Saturday, Dec 21, from 11:30 am - 1:15 pm at The Burren (247 Elm Street) in Somerville. Tickets are $25 in advance, $30 at the door, $10 for students.

Continuing their holiday movie screenings, Trident Booksellers & Cafe (338 Newbury St) in Back Bay will show Love Actually on Saturday, Dec 21, from 7 pm - 9 pm upstairs in the cafe. Seating begins at 6:30. Tickets are free and not required but help the cafe gauge interest.

Support City of Goodness, Ukraine’s largest shelter for women and children, at the Ukrainian Christmas Concert at Harvard-Epworth United Methodist Church (155 Massachusetts Ave) in Cambridge on Saturday, Dec 21, from 6 pm - 7:30 pm. Featuring songwriter, producer, and Ukrainian folk singer Valeria Vovk and Ukrainian jazz pianist Fima Chupakhin, this will be an evening of beloved carols, candlelight, and festive cheer. Tickets are $35.

Indulge in an all-out Irish Christmas extravaganza with Fairytale of New York, coming to Citizens House of Blues (15 Lansdowne St) on Saturday, Dec 21, at 8 pm. Tickets start at $25.

Jolene Cuisine is coming to The Maso Studio at Huntington Theatre (264 Huntington Ave) to perform her first-ever Christmas special, A Very Hairy Christmas. Beginning at 8 pm on Saturday, Dec 21, join Jolene for a night of campy merriment and Christmas classics. Tickets are $25.

happening in Boston all weekend

Bakey Babka, known for their fresh babka treats, will serve up Brulée Babka for one last time this weekend.

These sweet treats will be available at their downtown location (151 Trement St) from Friday, Dec 20 through Sunday, Dec 22, from 10 am - 3 pm (or until they run out).

This is the last weekend for the annual SoWa Winter Festival at SoWa Power Station (550 Harrison Ave). $10 to enter; Children under 12 enter for free.

Head to the Mandarin Oriental (776 Boylston) in Back Bay for Louis Roederer champagne cocktails, live holiday jazz performed by Berklee College of Music students, light caviar, and bar bites at the pop-up Holiday Champagne Bar. The bar is open from 5 pm to 8 pm on 20, 21, and 31.

friday, december 20

classes

Learn to make Pasta all' Amatriciana with Eataly Boston (800 Boylston Street) in the Prudential Center in Back Bay on Friday, Dec 20, from 3 pm - 4 pm. Tickets are $85 and include a curated antipasto, wine pairings, plus ingredients to make (and enjoy) pasta all’ amatriciana during the class.

holiday events

Celebrate National Ugly Sweater Day at Lamplighter Brewing Co’s (110 North First Street and 284 Broadway) Annual Ugly Sweater Party this Friday, Dec 20. Beginning at 5 pm, enjoy festive beers and holiday vibes while wearing your best, ugliest sweater.

tastings

Learn about Trillium’s Wake Robin Bourbon during a guided tasting on Friday, Dec 20, from 6 am - 7:30 pm at Trillium - Fort Point. For $40, enjoy three samples of their Wake Robin lineup upstairs in the Headroom Hi-Fi Lounge, the distillery’s hi-fi listening lounge.

saturday, december 21

classes

Learn how to make Origami Ornaments with Ko-Kyoto on Saturday, Dec 21, from 11 am to 12 pm Upstairs at Bow Market (1 Bow Market Way) in Somerville. Tickets are $5.

Pottery with a Purpose returns to Boston this weekend with a Holiday Edition Pottery Class on Saturday, Dec 21, from 12 pm - 2 pm at Harpoon Brewery & Beer Hall (306 Northern Ave) in Seaport. For $75, participants will get an introduction to pottery making, including the pinch pot and coil technique, and a Beginner Pottery Kit containing enough materials to make one to three pieces during the class.

tastings

Come to The Urban Grape (303 Columbus Ave) in Back Bay on Saturday, Dec 21, between 2 pm and 5 pm for The After Brunch, their weekly free wine tasting. In addition to wines, this week, they’re featuring small-batch ceramics from Made with Mudd

If you’re still searching for the perfect holiday gift, head to Brix Wine Shop (1284) in the South End on Saturday, Dec 21, between 4 pm and 6 pm for a free wine tasting. They’ll have a wide variety open, from elegant reds and crisp whites to celebratory sparklers, all worthy of being under the tree.

holiday events

Celebrate the official start of winter on Saturday, Dec 21, from 2 pm - 4 pm at the Winter Warmer on the Greenway Party on the Rose Kennedy Greenway. Come down to Rings Fountain (Atlantic Ave & Milk Street) to enjoy the free hot chocolate bar, Holiday Toy workshop, bubble house, photo booth, live music, and instrument petting zoo while enjoying the return of Hatchlings.

Get fabulous and festive at the Sleigh All Day: Drag Brunch & BINGO, held from 1 to 2:30 pm at Time Out Market Boston (401 Park Drive) near Fenway

If you missed Small Mart’s first artisan market this month, don’t worry. The Vintage, Makers, & Artisan Market will be held again this weekend, on Saturday, Dec 21, from 11 am to 4 pm at the Crystal Ballroom (55 Davis Square) in Somerville. Grab a festive drink from the full bar and shop over 40 local artisans, vintage shops, makers, and more.

The Brighton Holiday Bazaar, “Boston’s largest indoor holiday market,” returns to Roadrunner (89 Guest St) this Saturday, Dec 21, from 11 am - 7 pm. Come listen to live DJ sets and sip on festive cocktails while you shop over 130 vendors. Tickets are $10 in advance and $15 at the door.

sunday, december 22

wellness, classes, + DIY

Start your Sunday (Dec 22) with a Pilates & Sound Bath class on the second floor of Quincy Market (206 South Market Street). Movement with Jill leads the class, which runs from 10 am to 11:15 am and costs $25.

Short Path Distillery (71 Kelvin St) in Everett is hosting DIY Holiday Gifts: Custom Bath Salt Blending with The Cozy Artist on Sunday, Dec 22, from 3 pm - 4:30 pm. Tickets are $35 and include Epsom salt, herbal mixins, essential oils, and gift-quality packaging. Cocktails will be available for purchase to enjoy during the class (but you’re not required to).

The Long Live Roxbury Tap Room in Roxbury is hosting a Christmas Vintage Cake Decorating Class on Sunday, Dec 22, from 1 pm - 3 pm. For $65, learn how to decorate using different piping styles, ribbons, and pearls. The cake provided will be vanilla chiffon with chocolate ganache and strawberry filling, frosted with vanilla Swiss buttercream.

tastings

Just in time to figure out which bottles of wine to stock up on for the holidays, The Urban Grape (303 Columbus Ave) in Back Bay is holding free holiday wine tastings beginning Sunday, Dec 22, from 1 - 4 pm. If you can’t make Sunday’s tasting, they also have free wine tastings on Monday, Dec 23, from 5 pm - 8 pm, and Tuesday, Dec 24, from 1 pm - 4 pm.

reoccurring winter events

As a reminder, the Commuter Rail has $10 weekend passes, which gives the ticketholder unlimited travel on Saturday and Sunday. Pass is activated during your first trip on Saturday and continues to stay active until Sunday night.

tastings + classes

Love Child holds free wine tastings every Friday (5 pm - 7 pm) and Saturday (12 pm - 3 pm) at their South Boston (364 West Broadway) location. These tastings are free and require no reservations.

Come to The Urban Grape (303 Columbus Ave) in Back Bay on Saturday for The After Brunch, between 2 pm and 5 pm, for their weekly free wine tasting.

To start your weekend off with a dose of wellness, come to The Hidden Art Gallery (25 Myrtle Street) in Beacon Hill for their weekly Explore Meditation with Watercolor class. Held every Friday from 3 pm - 6 pm, learn the basics of meditation while intuitively creating with watercolor. Classes are $55.

seasonal things to do

Historic Holiday Strolls — guided tours among the holiday lights on Boston’s Freedom Trail — continue on select Fridays and Saturdays through Dec 28. The walks are one hour long and led by guides dressed in 19th-century Dickensian costumes. For tickets and more information, visit the Freedom Trail’s website.

Boston Common’s Frog Pond Skating Rink (38 Beacon St) is open daily from 10 am - 10 pm, with the last entry admitted 30 minutes before closing. Anyone 58 inches or taller must pay $10 to skate. You can also rent skates ($15 for adults, $10 for kids), rent lockers, and get your skates sharpened ($7).

holiday markets + festivals

Boston’s annual Winter Festival Charlestown’s Hood Park (500 Rutherford) continues through Jan 25, with limited days and hours beginning at the end of the month. Spread out across two acres, there is an ice skating rink ($20/hr for adults, $15/hr for kids under 10; $10 skate rental), life-size light up castle, artisan marketplace, Veuve Clicquot Après Ski Gondola lounge, and more. Admission is free. Attendees can park in the Hood Park garage (100 Hood Park Dr) for free for up to three hours.

The annual Holiday Market at Snowport (65 Northern Ave) is now open in Boston’s Seaport District. It runs seven days a week (except Thanksgiving and Christmas Day) and features over 120 vendors, great food options, cocktail bars, live music, activities (like curling), and more. East Boston favorite Petrova Chocolates (creator of those viral Dubai Chocolate Bars) has a booth, so be sure to stop by! 

Farmer’s Market season never ends in Boston; it just moves inside. Visit Somerville’s Winter Farmer’s Market every Saturday from 9:30 am - 1:30 pm inside The Center for the Arts at the Armory (191 Highland Ave).

holiday bars + high teas

For the month of December, Publico (11 Dorchester St) has converted its open-air atrium into a winter wonderland, giving guests an immersive festive experience for lunch, dinner, drinks, and weekend brunch. At The Winter Market, you’ll be transported to the heart of a European Christmas Market and relive the joy of cozy childhood Christmases. Grab a seat by the fire and marvel at the towering 16-foot holiday tree. Reservations are strongly recommended.

Beacon Hill Books & Cafe is hosting its annual Holiday Tea service from 11 am to 5 pm every Sunday and Monday in December. Reservations are strongly recommended.

Boston’s only Hanukkah pop-up bar is back again this year. From now until Jan 1, you can visit Macabee Bar inside The Charles Hotel (1 Bennett St) in Harvard Square every Monday - Saturday starting at 4 pm. There are limited reservations available; priority is given to walk-ins.

To get festive above Boston, visit ViewBoston’s Stratus Winter Oasis. At the top of Prudential Tower (800 Boylston), Status Bar has been transformed into a winter wonderland where guests can sip festive cocktails while the city glitters around them. Tickets are $38, including admission to ViewBoston exhibits and one beer, wine, or signature cocktail. This also gives you access to The Beacon bistro, View Boston’s restaurant.

To literally warm up after a Snowport visit, book a table at Deck 12’s heated rooftop outdoor bar (65 Seaport Blvd). Like in previous years, there is an Apres theme, complete with heaters, fondues, chair lifts, gondolas, and more. Reservations are strongly recommended.

Or, head down the street to Harpoon Brewery & Beer Hall (306 Northern Ave) and get an infusion of festive cheer at the Holly Jolly Holiday Bar. Tickets are $18 and include a 90-minute reservation and one holiday-themed cocktail or mocktail.

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