The Harvard Square Business Association welcomes you to attend Winter Carnival 2026! The temperatures may be dropping but we are gearing up for some of the most highly anticipated events of the year, including the 18th Annual Taste of Chocolate Festival and the 16th “Some Like it Hot” Chili Cook-off. In addition to these signature events, there are activities and events happening in our restaurants, stores and cultural institutions.
Due to frigid temperatures scheduled for this weekend, the Taste of Chocolate Weekend has been posted until January 30th – February 1st.
The Chocolate Tasting Event will now take place at 1pm on Saturday, January 31st.
January 23rd – 25th
18th Annual Taste of Chocolate Weekend and Chocolate Tasting Event
The wait is over! The Harvard Square Business Association is delighted to announce the return on the 18th Annual Taste of Chocolate Festival! From January 23rd through the 25th, Harvard Square’s finest restaurants and cafes will embark on a three-day chocolate extravaganza! Our restaurants will feature chocolate desserts and cocktails while Harvard Square retailers will dazzle you with scrumptious chocolate specials and deals.
Tasting Event January 24th
The centerpiece of this beloved and eagerly anticipated sweet weekend is our free Chocolate Tasting Event taking place on Brattle Street (between Eliot and Church Streets) from 1pm – 2:00pm. More information coming soon.
harvardsquare.com, 617-491-3434
January 30th & February 6th
Hasty Pudding Man and Woman of the Year Events
Every year, the Hasty Pudding Theatricals bestows the Man of the Year (MOY) and Woman of the Year (WOY) awards on performers who have made lasting and impressive contributions to the world of entertainment. This year’s Man of the Year honoree is Michael Keaton. The recipient of the Woman of the Year Pudding Cup will be announced soon.
January 30th – Woman of the Year Parade and Roast
The Woman of the Year award dates back to 1951 with our first honoree Gertrude Lawrence. Since then, recipients have included the likes of Elizabeth Taylor, three-time Oscar winner Meryl Streep, Halle Berry, Sandra Bullock and Anne Hathaway. We’ve also honored First Lady Mamie Eisenhower and comedy legends, like Lucille Ball.
February 6th – Man of the Year Roast
The Man of the Year Award began in 1967 with Bob Hope and the subsequent recipients list reads like a who’s who of Hollywood’s leading men: Sean Connery, Tom Hanks, Robert De Niro, Robert Downey Jr., Justin Timberlake, and James Franco to name just a few.
Hasty Pudding Theatricals, 45 Dunster Street, 617-495-5205
February 7th
16th Annual “Some Like It Hot” Chili Cook-off
It is with great anticipation that the Harvard Square Business Association announces the return of the 16th Annual Some Like it Hot Chili Cookoff. This free chili tasting party will take place Saturday, February 7th on Brattle Plaza (in front of Bluestone Lane at 27 Brattle Street) from 1:00pm – 2:30pm and will be hotter and spicier than ever before! Some of Harvard Square’s most popular restaurants will be making batches of chili for this fun and festive event. Taste them all and vote for your favorite! The restaurant with the most votes will be awarded with the highly coveted Harvard Square Chili Pot!
harvardsquare.com, 617-491-3434
February 12th – 16th
Lovin’ in the Square: Valentine’s Day Events
Romantic dinners, intoxicating cocktails, decadent desserts, one-of-a-kind gifts and so much more! There’s love in Harvard Square! Our businesses are offering you sweet and heartfelt gifts and experiences for all of your favorite people. This year’s Valentine’s events feature fabulous food and drinks from Harvard Square’s restaurants, romantic and fun deals from our retailers and a variety of intimate, cozy and entertaining things to do from our cultural icons. Whatever your heart desires, you’ll find it on our historic streets! More information coming soon!
harvardsquare.com, 617-491-3434
February 8th
Superbowl LX
Find your spot to watch the big game! Restaurant promotions coming soon!
harvardsquare.com, 617-491-3434
March 1st
Dr Seuss 122nd Birthday Party at the Harvard Coop
The Harvard Square Business Association, in partnership with the Harvard COOP, excitedly announces a Dr. Seuss Birthday Party and a hats off to reading celebration in honor of the beloved children’s story teller’s 121st birthday! Join us on March 1st for all things Seuss! In Harvard Square, ‘from there to here, here to there, funny things are everywhere!’ More details coming soon!
harvardsquare.com, 617-491-3434
March 13th – 17th
Harvard Go Bragh – St. Patrick’s Day Events
Rejoice in all things Irish for St. Patrick’s Day! Special in-store and restaurant promotions and cultural activities inside our arts member organizations will be announced soon.
harvardsquare.com, 617-491-3434
February 22nd – March 7th
Boston Dine Out Weeks in Harvard Square
Get ready for two weeks of mouthwatering prix fixe meals from Harvard Square’s restaurants.Dine Out Boston offers visitors and locals the perfect opportunity to discover why Cambridge is one of the culinary capitals of the world! Held twice-yearly by Meet Boston in partnership with participating restaurants, restaurant week features prix fixe menus at multiple price points for lunch and dinner. A full list of participating restaurants will be announced soon!
harvardsquare.com, 617-491-3434
Through February 8th
Wonder at the American Repertory Theater
From the theater that brought you Gatsby, Waitress, and Jagged Little Pill comes a new musical about change, identity, and what it means to belong. Featuring a driving, pop-inspired score by the GRAMMY Award®-winning duo A Great Big World (“Say Something,” “This Is the New Year”) and a book by MacArthur Fellow and Pulitzer Prize finalist Sarah Ruhl (Eurydice; The Clean House; Smile, a memoir), this uplifting show celebrates empathy, resilience, and the power of choosing kindness. Click here for tickets.
American Repertory Theater, 64 Brattle Street, 617-547-8300
January 15th and 16th
Boston Celtic Music Festival at Passim
The 23rd annual Boston Celtic Music Festival, known as BCMFest, returns to Club Passim, Crystal Ballroom, The Burren, The Rockwell, and Arts at the Armory January 15-18, 2025. Presented by Passim, a Cambridge-based non-profit that supports a vibrant music community through Club Passim, the Passim School of Music, artist grants, and outreach initiatives.
The 2026 festival will showcase Greater Boston’s deep tradition of music, song and dance from Irish, Scottish, Cape Breton, Quebecois and other Celtic communities. BCMFest features acts that are traditional as well as others that draw on contemporary sounds and ideas; full-time, professional touring acts as well as local session musicians; highlighting performers from across the generations.
Click here to see the full line-up and purchase tickets to all parts of the festival.
Passim, 47 Palmer Street
January 19th
Belmont World Film’s Family Festival at the Brattle Theatre
Belmont World Film’s 23rd Family Festival is a celebration of some of the world’s most imaginative films for and about children, brought to life on the big screen as a shared experience.
For a full listing of films and tickets, click here.
Brattle Theatre, 40 Brattle Street
January 24th
Katie Hannigan at The Comedy Studio
Katie Hannigan is a stand-up comic, actor, and writer. Her stand-up has been featured on The Late Show with Stephen Colbert, Comedy Central, Just For Laughs New Faces, The Late Late Show with James Corden, and MTV. Her debut album, Feeling of Emptiness, was named Ten Best of 2022 by the Interrobang. Katie is a member of SAG-AFTRA and has appeared in That Damn Michael Che on HBO, City Island, on PBS Kids, commercials for Subway, Cheez-Its, Mabelline, Home Depot, and many indie films and sketches. Katie’s writing credits include the original series Death Hacks starring Thomas Middleditch and Kristen Schaal, from Augenblick Studios. She also hosts the popular podcast Lady Journey with comedian Sarah Tollemache.
The Comedy Studio, 5 3/4 JFK Street
January 24th – May 10th
Critical Printing at Harvard Art Museum
With its unexpected juxtapositions among little-known prints, this installation is designed to generate experimental thinking. In the related course (AFVS 215), taught by Jennifer L. Roberts (History of Art and Architecture) and Matt Saunders (Art, Film, and Visual Studies), students explore printmaking as both makers and scholars. Moving between the studio, the seminar room, and the museum, they learn multiple print techniques and study fundamental themes in the history and theory of printmaking.
The subsections of the installation, which cut across the grain of the course syllabus, consider prints in a field of matter, space, energy, and time. Prints can slip between dimensions and open portals between worlds. Prints can store and release energy or hold fluid substances in suspension. Prints can host a burst of biological imagination or offer an encounter with the silent eternity of stone. In the unorthodox groupings on these walls, new approaches to the medium and new avenues for research are waiting to be discovered.
The University Teaching Gallery serves faculty and students affiliated with Harvard’s Department of History of Art and Architecture. Small-scale, semester-long installations are mounted here in conjunction with undergraduate and graduate courses, supporting instruction in the critical analysis of art and making unique selections from the museums’ collections available to all visitors.
This installation is made possible in part by funding from the Gurel Student Exhibition Fund. Modern and contemporary art programs at the Harvard Art Museums are made possible in part by generous support from the Emily Rauh Pulitzer and Joseph Pulitzer, Jr., Fund for Modern and Contemporary Art.
Harvard Art Museums, 32 Quincy Street
January 31st
One Year Anniversary Party: Step Into a Romance Novel at Lovestruck Books
We’re Bringing The Romance Novel Alive to Honor Our 1 Year Anniversary. Photo Opps, Custom Treats, and More Bookish Fun Await!
Can you believe it’s already been a year of swoons, stories, and happily-ever-afters at Lovestruck Books & Cafe? In honor of this Lovestruck landmark we’re bringing the romance novel alive and inviting you to step into the story! After an all day celebration, we’re closing down for a private party where the store will be transformed into your very own romance novel. Join us in celebrating our very first anniversary and step into the story.
We have a swoon-worthy lineup of activities to look forward to. Click here for tickets.
Lovestruck Books, 44 Brattle Street, 617-286-2346
February 3rd
MAIN STAGE: Celebrity Series of Boston | Axelle Fanyo, soprano & Julius Drake, piano at Longy School of Music
French soprano Axelle Fanyo makes her Boston debut with a captivating program showcasing the vocal brilliance and emotional depth that have defined her rising career on opera and recital stages. Praised for her extraordinary expressiveness, Fanyo “does not only embody a character, she tells us the story. She clearly cultivates the art of communication, which gives her singing another dimension” (Forum Opéra). Click here for tickets.
Longy School of Music, 27 Garden Street
February 6th & 7th
Black-Owned Business Marketplace Pop-up
By Sustainable Business Network of Massachusetts
One Brattle Square
Join us for a vibrant showcase of local Black-owned businesses at Harvard Square’s Black-Owned Business Marketplace Pop-up!
Celebrate Black History Month and show your love for Black-Owned Businesses. Hosted by the Cambridge-Somerville Black Business Network, in partnership with the Sustainable Business Network of Massachusetts, Cambridge Local First, Eastern Bank, and the Harvard Square Business Association, we invite you to the Show Your Love for Black-Owned Business Marketplace!
Friday, Feb. 6, 2026, 12:00 PM – 7:00 PM
Saturday, Feb. 7, 2026, 11:00 AM – 7:00 PM
Explore unique, hand-crafted gifts, soaps, sauces, bags, jewelry, and more from than a dozen amazing vendors over two festive days! Don’t miss this opportunity to find one-of-a-kind holiday treasures while supporting Black-owned businesses. See you there!
Sponsors include Beacon Capital Partners, City of Cambridge, Eastern Bank, and Harvard Square Business Association.
Sustainable Business Network of Massachusetts, 99 Bishop Allen Drive, 617-395-0250
February 11th
Earfull at Regattabar
Authors: Thomas Beller, John Sayles
Musicians: The Lo-i, Chris Smither
EARFULL is a performance series featuring writers and musicians doing their respective things in an intimate setting. WRITERS read from their new books, or about-to-be books, or right from their crumpled up notes. MUSICIANS range from harpists to horn blowers, from singer-songwriters to full-on rock bands. EARFULL EVENINGS offer food & drink at the venue, and time between acts to socialize. On Wednesday, Feb 11, we welcome authors Thomas Beller and John Sayles, and musical acts The Lo-i and Chris Smither. More information and tickets, click here.
Regattabar, 1 Bennett Street, 617-395-7757
February 21st
Blue Heron’s In Praise of Laura Peverara: Madrigals for the Concerto delle donne (Ferrara, 1580s) at First Church in Cambridge
In the 1580s, Ferrara boasted one of the most famous vocal ensembles in Europe: a trio of women known as the Concerto delle donne. One member, Laura Peverara, was so admired and beloved that she inspired two madrigal anthologies, published in 1582 and 1583. We present a selection of this rich repertoire, including music by Wert, Marenzio, Luzzaschi, and others. Click here for tickets.
Blue Heron, 950 Watertown Street, 617-960-7956
March 5th – 8th
Celebrity Series Jazz Festival at Arrow Street Arts
Celebrity Series returns to Arrow Street Arts—Harvard Square’s versatile theater and entertainment hotspot—when Jazz Festival returns! Catch exciting next-generation artists who understand and embrace the art form’s limitless capacity for freedom and self-expression.
Experience an electrifying atmosphere where rhythm moves through the crowd, melodies spark emotion, and every performance creates an unforgettable connection between artists and audience. Secure your tickets now to experience the return of this immersive jazz club experience! Click here for tickets.
Arrow Street Arts, 2 Arrow Street, 617-299-2300
March 6th
Steven Forbert at Passim
Steve Forbert is a true American treasure, a fact underscored by his 21st album, Daylight Savings Time. Like all his albums of original songs, it’s suffused with what venerated rock journalist Robert Christgau discerned as his “omnivorously observant” songwriting, marked by Steve’s gift for finding the deeper meaning and magic within the spectrum of everyday moments, as well as his abundant melodic and poetic enchantment. Click here for tickets.
Passim, 47 Palmer Street
March 11th
Amelia Day at The Sinclair
Amelia Day is a musical jack-of-all-trades. Standing at the intersection of folk, rock, and pop, Day blends heartfelt storytelling, raw delivery, and unforgettable melodies into music that feels both fresh and familiar — like rediscovering an old favorite. A self-described writer before anything else, her perceptive lyricism extends far beyond her 23 years, with lines reminiscent of songwriting greats like Joni Mitchell and Paul Simon. As the Spokesman-Review notes, Day has a signature style that features “wordplay, double-meanings and rhythmic variations,” with themes ranging from journeying into adulthood to climate change. Many of Day’s songs are also shaped by her intimate relationships, where her queerness and candor take center stage. Day’s upcoming EP EGO TRIP is her most personal project yet. Click here for tickets.
The Sinclair, 52 Church Street, 617-547-5200