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Hilliards Chocolate valentines
Photograph: Courtesy Hilliards Chocolate

The best Valentine’s events at Time Out Market Boston

We have so many fun things coming up that you don’t want to miss.

JQ Louise
Written by
JQ Louise

Valentine’s Day is right around the corner and there are so many fun activations happening at Time Out Market Boston. From a local chocolatier pop-up to a chocolate and wine pairing class to a local artisan market, there are plenty of reasons to visit us in the Fenway neighborhood next month. Read our guide to Valentine’s Day in Boston for lots more ideas on how to make the best of the season.

Time Out
Time Out

1) Hilliards Chocolate Pop-up

Hilliards Chocolates, one of New England’s most beloved artisan brands, will be having a Valentine's Day chocolate pop-up from Friday February 10th - Monday February 13th. Come by and pick up some sweets!

2) The He-Art of Chocolate

Hilliards Chocolate
Photograph: Courtesy Hilliards Chocolate

Copy: Join us for a night of chocolate and wine pairings. Hilliards Chocolates & Pour Decisions are hosting this fun event on Friday, February 10th from 7-8:30pm. Hilliards has been creating artisan chocolates since 1924 and we can’t think of a better way to get in the Valentine’s Day spirit than sampling a few of them (especially with a glass of wine in hand)! 

Tickets are $35 and include: 
Four chocolate samples
Four wine samples
$10 TOM Card to grab a drink or some food in the market after the event. 

3) Spread Love Market 

Time Out
Time Out

On Saturday, February 11th, Time Out Market Boston and Black Owned Bos. will be hosting the Spread Love Market. From sweet treats and cards to clothes and accessories the collective is sure to offer something that special someone will love and you may even find something for yourself while you are at it! 


  • Niraji
  • True 9 Accessories 
  • Sweet Glam 
  • Krio skincare 
  • Ankhara By Luciana Home Decor & Designs 
  • Stinky's Kittens & Doggies Too
  • BGM Apparel 
  • Lumiere Rene Candle Co 
  • Akosua's Closet 
  • Emerald City Plant Shop

4) Galentine’s Day Sip & Script 

Join Sip & Script at the Time Out Market Boston for a night of crafting and conversation!

Whether you’re a stationery nerd looking to pen your own cards, a DIY bride or just an avid crafter, this workshop will give you a friendly introduction to modern calligraphy using a pointed dip pen and ink. Learn the basics of using a beginner’s calligraphy kit (that’ll be yours to keep) while enjoying a complimentary cocktail from the Time Out Market Bar. Grab a ticket and get ready to deck out all of your own thank you notes, place cards, home decor, and more with dazzling penmanship. 

5) Dating Game Show

Time Out
Time Out

Join us on February 23 from 6-9pm for our first ever Dating Game Show! Watch as bachelors and bachelorettes quiz their potential dates. Hosted by our favorite Drag Queen, Plane Jane, the night will be filled with laughs whether you are a contestant or an audience member. DM us on @timeoutmarketboston if you want to be a contestant yourself (must be 21+), but throughout the evening audience members can also test their luck with Time Out Market's “Scratchmakers Game”, where you may also match with someone! The winning couples get a gift card for a dinner at Mooncusser, including the chef’s tasting menu with wine pairings. 


  • 6 pm: DJ Takes the Stage
  • 7 pm: Round one of the Dating Game Show starts
  • 7:45 pm: Plane Jane leads a round of ScratchMakers Game
  • 8 pm: Round two of the Dating Game Show starts

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