Valentine’s Day Events Happening in Boston

From a 'naked' scavenger hunt to swing dancing in South Station, here are a bunch of fun ways to celebrate Valentine's Day around Boston.


The Brattle Theatre is screening Casablanca this Valentine’s Day. / Warner Bros.

Romantic Valentine’s Day Events

Movies, museum adventures, dinner cruises, and more.

Boston Wine Fest Dinner Dance and Wine Brunch

The Boston Wine Festival is offering two ways for couples to wine and dine this Valentine’s Day. Their Dinner Dance on Saturday the 14th will be an all-champagne dinner with wines from Moët & Chandon, plus live music and dancing. The Wine Brunch on Sunday morning will feature Creole dishes and live music from a New Orleans jazz band.

$215 for dinner on Saturday, February 14 (7 p.m.), $95 for brunch on Sunday, February 15 (various times), Boston Harbor Hotel, 70 Rowes Wharf, Boston. More info: dinnerbrunch.

Valentine’s Day Cruises

Hope aboard the Odyssey or the Seaport Elite for a romantic Valentine’s Day weekend on the water. Trips are available for dinner and brunch—roses and champagne are included, of course.

Prices and times vary,

Casablanca and Secretary at the Brattle

For a classic love story with iconic lines every five minutes, head to the Brattle on Valentine’s Day to watch Casablanca, starring Humphrey Bogart and Ingrid Bergman as former lovers who meet again in—of all the gin joints—his. Or, for raunchier programming, consider the original Fifty Shades of Grey, Secretary, the 2002 erotic romance starring Maggie Gyllenhaal and James Spader as Mr. Grey.

Casablanca: various times Friday-Saturday, February 13-14; Secretary: midnight, Saturday, February 14; Brattle Theatre, 40 Brattle St., Cambridge, 617-876-6837,

Love to Cook, Cook for Love

For couples with a shared appreciation for the kitchen, take this cooking class hosted by New England Fun. Singles are also welcome to sign up for the lesson, where a professional chef will teach you how to make a romantic seven-course meal.

$85, Saturday, February 14, 7-10 p.m., New England Center for Arts and Technology, 23 Bradston St., Boston,

Naked at the Art Museum Scavenger Hunt

No, you won’t actually be naked. This version of Watson Adventures’ scavenger hunt will send you on a tour of the MFA to locate nudes and other risqué works of art. Attend with your significant other for a romantic romp through the museum—or go with a friend for kicks and giggles.

$40, Friday, February 13, 6:30 p.m., and Saturday and Sunday, February 14 and 15, 1 p.m., Museum of Fine Arts, 465 Huntington Ave., Boston,

Dining in the Dark and a Downton Abbey Dinner

Hampshire House is hosting two different unique Valentine’s Day dinners this year. Friday and Sunday, dine in the dark while enjoying music and a story. On Saturday, celebrate the 14th Downton Abbey-style. Dress in your early 20th-century best to celebrate the engagement of Lady Mary to Matthew Reginald Crawley.

Dining in the Dark: $75, Friday, February 13, and Sunday, February 15, 6 p.m.; Downton Abbey Dinner: $120, Saturday February 14, 6:30 p.m.; Hampshire House, 84 Beacon St., Boston, 617-227-9600,

Swing Dancing in South Station

For anyone who has ever breezed through South Station and thought, “This place needs dancing,” New School Swing agreed. Their free swing dance event will begin with a lindy hop lesson at 8 p.m., followed by the social dance from 9 to 11 p.m. with live music by Phil McGowan and the Easy Winners.

Free, Saturday, February 14, lesson at 8 p.m., social at 9 p.m., South Station, Boston,

Family-Friendly Valentine’s Day Events

A few ways to spend Valentine’s Day with the kids.

Salem’s So Sweet Chocolate and Ice Sculpture Festival

The chocolate and wine tasting kickoff is for adults, but visit Salem anytime February 6 through 15 to see 15 large ice sculptures placed throughout town. Weather permitting, the Salem Trolley will give rides around the festival route February 7 and 8.

Free to attend, February 6-15, Downtown Salem,

Bugs Bunny Film Festival

What’s love got to do with this? Nothing, really, other than our love of Looney Tunes. The 20th annual Bugs Bunny Film Festival kicks off on Valentine’s Day this month at Brattle Theatre, a perfect diversion for the whole family to enjoy. The three programs showing all week are the “All Bugs Revue,” “Looney Tunes Revue,” and “Daffy Duck and Friends.”

February 14-21, Brattle Theatre, 40 Brattle St., Cambridge, 617-876-6837,

Valentine’s Day Comedy

Love and laughter go hand in hand.

Mortified’s Doomed Valentine’s Day Shows

The best part of being an adult? Not being an adolescent anymore. In Mortified’s “Doomed Valentine’s Day” shows at the Coolidge and the Oberon, speakers will go on stage one by one to share their super-awkward love stories, from first kisses, to prom, to failed adventures in flirting.

$15; Thursday, February 12, 7:30 p.m. at the Coolidge in Brookline; Friday, February 13, 7 p.m. at the Oberon in Cambridge.

Thorns at ImprovBoston

With rants, monologues, songs, and short films, let “Thorns” remind you that Valentine’s Day is about more than the lovey-dovey. Instead, spend the evening with comedians who’ll find the hilarity in heartbreak.

$18, Saturday, February 14, 10 p.m., ImprovBoston, 40 Prospect St.,

Anti-Valentine’s Day Events / Events for Singles

Parties, matchmaking, and paint night.

Love Sux at Howl at the Moon

Howl at the Moon’s annual Love Sux party is once again free if you bring a torn up, shredded, or mutilated picture of your ex. That about sums up the attitude of this party, which comes with plenty of Bud Lights, Skyy cocktails, and 24-ounce X-Boyfriends.

Free entry with photo, Saturday, February 14, 5 p.m., 184 High St., Boston, 617-292-4695,

Paint Nite

Single on Valentine’s Day? Never been to Paint Nite? You might as well kill two birds with one stone. You and your fellow single ladies will paint owls in love onto wine glasses, followed by a wine tasting and Taza chocolate.

$45, Saturday, February 14, 6:30 p.m., 230 Somerville Ave., Somerville,

Three Day Rule’s Boston Launch Party

Three Day Rule, a matchmaking service partnered with, is launching in Boston just in time for Valentine’s Day. As seen on Shark Tank, the service invites you and your friends to meet matchmaker McKenzie Faucher at Forum for a free beer and snacks.

$10, Wednesday, February 11, 6-10 p.m., Forum, 755 Boylston St., Boston,


Singles ready to mingle have a bunch of options to do so this Valentine’s Day season. Scenergy Dating is one of many, and they’re hosting two separate mixers before and after the 14th. These mixers target career-minded singles and will be moderated by their professionally trained staff. The “Netflirting” aspect involves using “Call Me Cards” to meet new people.

$25; 20s to 40s: Friday, February 13, 7-9 p.m., Lir Pub, 903 Boylston St., Boston; 30s to 50s: Wednesday, February 18, 6-8 p.m., Black Bay Social Club, 867 Boylston St., Boston.


Check out more of our Valentine’s Day guides.