What to do in Boston this weekend (Dec 19 - 21)

If you have an event, a new attraction, a hotel, or a restaurant opening you’d like me to cover, please reach out!

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Italian chocolatier opens on Newbury. Venchi, a 150-year-old Italian chocolate company, is expanding into Boston, offering a variety of chocolates, as well as hot chocolate, gelato, crepes, and more. The store is now open at 123 Newbury, under Diptyque. (Boston Restaurant Talk)

Brookline’s Barcelona Wine Bar plans expansion. The popular tapas restaurant is taking over the space next door, adding 2,700 square feet, a new service kitchen, and an additional dining room and bar. (Brookline News)

Chinatown’s newest tea spot. Chinese tea company, Molly Tea, has opened its second U.S. store in Boston’s Chinatown this week (67 Beach St). They offer a full menu of teas, including milk teas and brewed teas served hot or iced. For their opening weekend, they’re offering buy-one, get-one drink specials from Friday, Dec 19, through Sunday, Dec 21. (Joy Boston)

Chef George Mendes plans to open two South End spots in 2026. Former owner of Michelin-starred Aldea in NYC + former chef of Amar in Back Bay, he plans to open Agosto, an “intimate, tasting-menu focused restaurant with a chef’s counter” and Baby Sister, an adjacent bakery cafe. Both will feature items inspired by Mendes’ Portuguese heritage. (Boston Magazine)

American Airlines gives travelers more reasons not to choose Basic Economy. Effective as of December 17, AAdvantage loyalty members flying Basic Economy will no longer earn miles or Loyalty Points. (The Points Guy)

Get ready for more record-setting holiday travel. Over 120 million Americans are expected to hit the road or take to the skies between December 20 and January 1, according to AAA estimates. The worst traffic for Bostonians is expected on December 20 — specifically, I-95 N towards Portsmouth at 3:30 pm. This route is expected to take 3 hours and 43 minutes, a 126% increase in travel time.

Moleskine is now open in Seaport. Writers, rejoice: there is now a brick-and-mortar Moleskine (64 Harbor Way, Boston, MA 02210) for all of your notebook, planner, and sketchbook needs.

Yes, sunsets are getting later (but days are still getting shorter). Boston’s earliest sunset was actually back on December 8. Our sunrises, however, will continue to get later until January 3. Don’t worry; as of Dec 21, we do get more daylight, gaining a full minute more by the end of the month. (CBS Boston)

Changes are coming to Charlestown. There is a new plan to redevelop Piers 4 and 5 for a new public waterfront space, complete with meeting halls, classrooms, and sailing facilities. The downside: construction isn’t planned to begin until 2030. Plus, a 24,000-square-foot grocery store is being built in Hood Park, giving the neighborhood a second full grocery store. (Axios Boston)

Feel good news: A new way to recover takes root in Central Mass. Shawn Hayden, who runs the Gardner Athol Area Mental Health Association, is building a new type of recovery center for men with addiction and mental health issues. He converted a farmhouse into part housing, part animal sanctuary, with human residents bonding with and caring for the property’s farm animals. (WBUR)

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A curated rundown of unique events happening this weekend in and around Boston that I’m either attending or wishing I were. If you’re looking for weekly happenings, like wine tastings and yoga classes, scroll to the next section.

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See A Christmas Carol at Omni Parker House (60 School St, Boston, MA 02108), where Charles Dickens stayed and rehearsed, from Friday, December 19, through Sunday, December 21. Tickets are $35.

Catch A Seraphim Christmas, another Boston holiday tradition, on Saturday, December 20, and Sunday, December 21, in West Roxbury, Newton Centre, Cambridge, MA, or virtually. Tickets are $30.

Warm up at Curio Spice Co.’s Hot Cocoa Bar with free samples of their hot cocoa and winter spices at The Demo Stall at Boston Public Market (100 Hanover St, Boston, MA 02108) all weekend long.

Get your last-minute holiday shopping completed at The Holiday Stroll on Saturday, December 20, and Sunday, December 21, from 11 am to 6 pm at The Charles River Speedway (525 Western Ave, Brighton, MA 02135). There will be over 60 small businesses set up, selling art, vinyl, vintage, and more. Plus, don’t miss jar decorating, “candy-gram” card crafting, or the Gingerbead House building competition. Entry to the Stroll is free. Food and drink will be available for purchase.

Grab your friends that feel like family and head to the Chosen Family Party on Friday, December 19, from 9 to 11:30 pm, Upstairs at Bow Market (1 Bow Market Way, Somerville, MA). There will be tarot readings, cootie catcher crafts, and more. Tickets are $15 ahead, $20 at the door. $5 of every ticket goes to the Somerville Homeless Coalition.

Saperavi Brothers will be hosting a Georgian Wine Tasting on Saturday, December 20, at Petrova Chocolates (61 Salem St, Boston, MA) from 12 - 3 pm. Learn about the oldest wine-making country in the world and find the perfect bottle of natural wine for your holiday table or for under the tree.

Unwind with Holiday BINGO Night at Trident Booksellers & Cafe (338 Newbury St, Boston, MA 02115) on Saturday, December 20, from 7 to 9 pm. Come for the games, stay for the prizes, surprises, and holiday cheer. Tickets are $10. Seating is first-come, first-served and begins at 6 pm.

Get festive with Holiday Movie Night: The Muppet Christmas Carol on Saturday, December 20, from 7 to 10 pm Upstairs at Bow Market (1 Bow Market Way, Somerville, MA 02143). Tickets are $5 and include the Hot Cocoa bar. Food and drink will be available for purchase.

Celebrate a special Menorah Lighting on Sunday, December 21, from 4:30 to 5:30 pm at One Seaport Courtyard (60 Seaport Blvd, Boston, MA 02210).

East West Wines is hosting another Holiday Wine Tasting at Petrova Chocolates (61 Salem St, Boston, MA) on Sunday, December 21, from 1:30 to 6 pm. Try natural wines from Bulgaria and Serbia, plus grab last-minute gifts and stocking stuffers.

Spend the morning with the winter solstice in a special Sunday Morning Yoga flow with live piano at the Museum of Modern Renaissance (115 College Ave, Somerville, MA 02144), on Sunday, December 21, from 10 to 11:30 am. Tickets are $39.19.

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As a reminder, the Commuter Rail has $10 weekend passes, which give the ticket holder unlimited travel on Saturday and Sunday. The pass is activated during your first trip on Saturday and remains active until Sunday night.

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Shop the Charles River Farmers’ Market every Friday (12 - 6 pm) and Sunday (10 am - 3 pm) at The Charles Hotel (1 Bennet St, Cambridge, MA, 02138). During the winter, vendors are set up in red sheds and still have fresh bread, pasta, meat, and seasonal fruits and vegetables.

Jamaica Plain holds its weekly Farmers Market every Saturday from 12 pm to 3 pm year-round in the Bank of America parking lot (677 Centre St, Jamaica Plain, 02130).

Shop the legendary Haymarket, America’s oldest open-air market, every Friday and Saturday from 6 am to 7 pm. Vendors offer fresh, affordable produce, dairy products, meat, and seafood. Just steps from Boston Public Market and MBTA’s Haymarket Station.

Every Saturday from November 1, 2025, through April 11, 2026, you can shop for local and healthy foods at the Somerville Winter Farmers Market at Arts at the Armory (191 Highland Ave, Somerville, MA 02143). The market is held weekly from 9:30 am to 1:30 pm except for 11/29/25 and 12/27/25.

Shop trees, wreaths, and more at the family-owned Boston Christmas Trees (423 Washington St, Brighton, MA 02135) seven days a week from 8 am to 10 pm. After 50 years in Allston, BCT has moved to Brighton, where it can now accommodate free parking for three shoppers. Plus, they deliver.

Whether you’re shopping for a tree or want to soak up seasonal vibes, don’t miss visiting the Christmas Tree Farm at Assembly Row (301 Assembly Row, Somerville, MA 02145) now through Christmas Eve. Shop freshly cut trees, handcrafted wreaths, and more holiday decor to keep the festive vibes flowing all season long.

Shop small this holiday season at the Downtown Boston Holiday Market every Thursday, Friday, and Saturday at Summer Street Plaza (10 Summer St, Boston, MA 02110) through December 21 from 11 am to 4 pm. The market features a curated lineup of artisan vendors with a variety of goods perfect for the gift-giving season.

Sip and shop your way through the Holiday Shopping Market at Boston Public Market every Friday, Saturday, and Sunday through December 21. In addition to the vendors at BPM year-round, more will be popping up, including Damask Cakes, Joppapots, Wool & Weft, and more. Entry is free.

Boston’s biggest winter market, Snowport (100 Seaport Blvd, Boston, MA), returns for its 7th season beginning Friday, November 7, through December 28. The market will be open seven days a week, except for Thanksgiving and Christmas Day, with extended hours in December.

The SoWa Winter Festival returns for its 10th year at the SoWa Power Station (550 Harrison Ave, Boston, MA 02118) now through Sunday, December 28. The market is open daily except on Mondays, Christmas Eve, and Christmas Day. Shop over 125 local vendors, including Apritvo, Eataly Boston, Tiny Farmhouse by Amy McCoy, Clover B, Parkside Bookshop, and more. Entry is $10 (children under 12 are free).

Boston’s Winter Fest returns to The Yard at Hood Park (100 Hood Park, Charlestown, MA 02129) from Saturday, December 6, through December 30 (weekends only until Dec 19). Enjoy interactive family activities, rides, seasonal food and beverages, plus unique shops at the winter market. Tickets start at $7.22.

Every Saturday and Sunday from November 29 through Christmas, enjoy Crafts, Cocoa, & Cheer on the lawn at Assembly Row (355 Artisan Way, Somerville, MA 02145). From 1 to 3 pm, enjoy free hot cocoa, live music, holiday treats, and holiday-themed crafts while supplies last.

MASARY has once again transformed Mount Auburn Cemetery (580 Mt Auburn St, Cambridge, MA 02138) into Solstice: Reflections on Winter Light, an immersive outdoor journey. From Friday, December 5, through Sunday, December 21 (except Mondays + Thursdays), take a journey through light and sound as you weave through Mount Auburn’s outdoor and indoor spaces. Tickets range from $5 for youth to $85 for a timed elevated experience.

Step into an immersive winter experience at the Winter Garden in the Prudential Center’s South Garden (800 Boylston St, Boston, MA) from 4 pm to 9 pm beginning Thursday, December 4, through Wednesday, December 17. MASARY has created a “mesmerizing ballet of motion and color, inviting visitors to pause and wonder at the magic of winter nights.” This is a free event.

Need to warm up after a visit to Snowport? Head to Deck 12 (Yotel Boston, 65 Seaport Blvd, Boston, MA 02110) where their winter pop-up, Apres, returns from Friday, November 14, through Tuesday, March 3. Sit fireside and thaw out with a bowl (or flight) of chili or a seasonal cocktail while the Boston skyline glitters around you. Book your reservation now.

Warm up at Avery Bar Chocolat, returning to Avery Bar inside the Ritz-Carlton Boston (10 Avery St, Boston, MA 02111) every Saturday and Sunday through Sunday, December 28. Enjoy hot chocolates or cocoa lattes prepared table-side, with a choice of toppings and sweet treats meant to make your drink “perfectly nice” or “lusciously naughty.” Book your reservation.

The Holly Jolly Bar returns to Harpoon Brewery (306 Northern Ave, Boston, MA) from Thursday, November 13, through Sunday, December 28. The halls are decked from floor to ceiling, and the menus are filled with seasonal sips and bites that will fill you with festive cheer. Tickets are $19.90 and include a 90-minute reservation and one welcome cocktail (non-alcoholic options available).

Warm up with a cup of hot (milk, dark, or white) chocolate from the new L.A. Burdick Chocolates Pop-Up at Four Seasons One Dalton (1 Dalton St, Boston, MA 02115) now open daily from 12 to 8 pm.

Get into the spirit of the season at Miracle at Kimpton Marlow Hotel (25 Edwin H. Land Blvd, Cambridge, MA 02141) holiday pop-up bar from Thursday, Nov 20, through Sunday, Dec 28. There’s a whole new lineup of seasonal cocktails, served in a limited-edition Santa’s Head, SanTaRex, or Christmas Unicorn.

Get in the holiday spirit at the top of the Prudential Center (800 Boylston St, Boston, MA 02199) at View Boston’s Stratus Winter Oasis. Indulge in a festive cocktail or two while surrounded by festive décor and take in unforgettable city views. Note: A ticket to View Boston does not guarantee immediate entry to Stratus.

Every Friday in December, Short Path Distillery (71 Kelvin St, Everett, MA 02149) will transform its Barrelhouse Bar into a Whiskey Wonderland Cocktail Pop Up. The halls will be decked, and the menu will feature festive bites and cocktails, including curated cocktail flights and dessert or nightcap cocktails. Reservations required.

Step into Victorian England with Charles Dickens’ A Christmas Carol, performed by the Commonwealth Shakespeare Company at Emerson Cutler Majestic Theatre (219 Tremont Street, Boston, MA 02116) from Saturday, December 6, through Tuesday, December 23. Tickets range from $31.63 to $169.13.

Every Saturday from November 29 through December 20, there will be a Holiday Drone Show on Boston Common (139 Tremont St, Boston, MA 02111) from 6 to 8 pm.

The Holiday Pops with Boston Pops return to Boston Symphony Hall (301 Mass Ave, Boston, MA 02115) on Thursday, December 4 at 7 pm. Performances recur through Wednesday, December 24, and will feature fan-favorite classics like “The 12 Days of Christmas,” “Sleigh Ride,” “Jingle Bells,” and more. Tickets begin at $64.99.

Choreographed by Founder and Artistic Director Jose Mateo, Jose Mateo Ballet Theatre’s The Nutcracker returns for its 37th year at the Strand Theatre (543 Columbia Rd, Boston, MA 02125) through Sunday, December 21. This simplified rendition was originally choreographed in 1988 and involves over 100 children ages 6-18. Tickets begin at $78.

Another Boston holiday tradition, The Slutcracker, returns for its 18th season at Somerville Theatre (55 Davis Square, Somerville, MA) on Friday, December 5, at 8 pm. Shows recur every Friday, Saturday, and Sunday through Sunday, January 4. Tickets start at $49.95.

The Boston Ballet is celebrating the opening weekend of The Nutcracker, performed at Citizens Opera House (539 Washington St, Boston, MA 02111), from Friday, November 28, through Sunday, December 28. Tickets range from $50 to $315.

Boston Common Frog Pond Ice Skating is now open. Admission price is based on height: $12 for 58 inches and over, while anyone 58 inches and under is free. Locker rentals and skate rentals are also available.

You can find a full rundown of recurring walking tours, food tours, bus tours, and trolley tours of Boston in my Beginner’s Guide to Boston.

Start your weekend with a dose of wellness at The Hidden Art Gallery (25 Myrtle Street) in Beacon Hill, which hosts weekly Explore Meditation with Watercolor classes. Held every Friday from 3 pm - 6 pm, learn the basics of meditation while intuitively creating with watercolor. Classes are $55.

Reconnect with your ability to digest and rest during a Sound Bath Meditation with Ramon of Ib and Flow (247 Walnut St, Brookline, 02445). Sessions ($50) are held every Sunday.

Wind down from the weekend and prepare for the week ahead with a Grounding Meditation session every Sunday from 5 - 6 pm at Blissful Monkey Yoga Studio (663 Centre Street, Boston, 02130) in Jamaica Plain. Led by Licensed Mental Health Counselor Brennan Mallonnee, you will be guided through techniques on how to calm stress responses and practice trauma-informed grounding techniques for anxiety. Tickets are $20. Yoga mats, cushions, and blankets are available, but you can bring your own.

If you’re trying to bring balance into your life this year, start your Sunday brunch with a gentle yoga flow with Brewery Yoga at Lamplighter CX. The class is held every Sunday from 12:30 - 1:30 pm at Lamplighter Brewing Co.’s CX location (110 North First Street, Cambridge, 02141) in their upstairs taproom. Tickets are $25 and include a beer token or a complimentary non-alcoholic drink.

If you’ve always wanted to learn how to navigate Boston by bicycle but have been too intimidated to start, join a Weekend In-And-Back Guided Ride with A Better City TMA. On Saturdays and Sundays from 9 am to 1 pm this spring and summer, join a free, three-hour bicycle ride from one of the many bike paths outside the city (meeting location disclosed upon sign up) and traverse the Urban Loop through downtown before returning to the start location.

Whether you already love screenprinting or are completely new to this printing method, DARK MODE hosts DIY Screenprinting workshops at their storefront in Bow Market (1 Bow Market Way, #24) in Somerville on Friday (7 pm) and Saturday (6 pm and 7 pm) nights. Tickets are $45, including t-shirts.

DARK MODE also hosts Candle-Making and Intention-Setting Workshops every Thursday at 7 pm in their storefront at Bow Market in Somerville. Tickets are $50.

Spend your Friday learning to make classic Italian cuisine with Self Up Cooking Classes (19 Kingston St) in Downtown Crossing from 6 pm - 9 pm. Every week, they host an Italian Dinner with Tiramisu Finale cooking class and dinner experience, where you can learn how to make a three-course meal, including a luscious tiramisu for dessert. Tickets are $100 and include all ingredients.

Natural wine lovers, don’t miss the free wine tastings at Petrova Chocolates (61 Salem Street, Boston, MA) in the North End every Friday (3 - 7 pm) and Saturday (12 - 3). Each week, they open bottles of natural wines from Eastern Europe, such as Georgia, Bulgaria, and Greece. These tastings are free and require no tickets or reservations.

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

Coffee lovers, this one is for you. Every Friday at 10 am, Counter Culture Coffee (374 Somerville Ave) in Somerville opens their Training Center for free coffee tastings. Anyone can learn and connect over perfectly brewed, high-quality, sustainable coffee.

Come to DeLuca’s Market Wine Cellar (11 Charles Street, Boston, MA 02114) in Beacon Hill for a free wine tasting every Friday from 4 - 7 pm. Every week, resident wine expert Donovan handpicks a mix of familiar favorites and bottles from up-and-coming vineyards or hard-to-find vintages to share among participants. No ticket is required.

On Saturdays, Boston Harbor Distillery (12R Ericsson St, Boston, 02122) leads VIP tours ($50) and barrel-side tastings of their spirits ($20).