Check out an experimental Old Fashioned menu at Chattermark Distillers on Saturday

This Saturday, all day from 2-11pm, Chattermark is serving up an awesome, experimental Old Fashioned cocktail menu.

YMCA is hosting an Arctic themed open-swim and an open house for their spring programming on Saturday

Bundle up and jump in! Join the Y for an arctic-themed open swim full of family fun and winter-inspired splashes. Don’t miss the fun!

Registration is open to all for our Early Spring program sessions. Staff will be on site to help with registration or answer any questions you may have this Saturday, January 31st 10am – 12pm and then again 2pm – 3pm during Arctic Family Swim.

Eat and Drink in an Igloo

Grab a group of friends and head to The Anchor for an igloo experience! Whether you want to bask in the sun during the day or enjoy Boston’s skyline at night, you don’t want to miss this winter activity. There is a food and beverage minimum, so come hungry and thirsty! Make a reservation here! 

Warm up with Tatte’s Seasonal Black Sesame Latte

If you haven’t tried Tatte’s Seasonal Latte’s yet – here’s your sign. Right now they are brewing up a Black Sesame Latte!

Check out WINTERACTIVE 2026 – Free Art, Rocket Ships & Giant Googly Eyes

Bundle up and explore. The third annual WINTERACTIVE Outdoor Art Exhibit officially kicks off this week, turning the streets of Downtown Boston into an open-air art walk that’s free, walkable, and totally photo-worthy.

Here’s what you’ll find as you wander:
✨ Whimsical interactive installations — think glowing seesaws and light-up figures 
🚀 A rocket ship perched on a rooftop over Winthrop Square — yes, really.
👀 Giant googly eyes on downtown buildings — perfect backdrop for your next social post.
🌸 A surreal forest of trumpet flowers, and more surprises tucked around corners throughout the neighborhood.

This year’s exhibition stretches across a record number of sites  (17 total) and brings together art and playful installations designed to activate Downtown through the end of March. Read more about it, here!

Pop over to Eastie and check out The Rink at The Tall Ship

Introducing The Rink at The Tall Ship in East Boston! Boston’s most iconic waterfront destination is about to make waves – this time, on ice.❄️⛸ Navy Yard Hospitality Group, in partnership with the Massachusetts Port Authority (Massport), is thrilled to announce the preview opening of The Rink at The Tall Ship, taking place this weekend, January 16. The preview marks the first phase of a new seasonal transformation of East Boston’s iconic waterfront venue. This initial soft launch offers guests an early look at the outdoor ice rink and select programming, with a full grand opening scheduled for February 11, 2026, when additional features, amenities, and experiences will debut.  Get all the details here! 

The Rink at The Tall Ship will offer a layered, immersive experience featuring:

• Outdoor Ice Rink with Skating Loop: Public skating for all ages, seasonal
  programming, special events, and group outings.
• Ice Bumper Cars: A unique, high-energy attraction for families, groups, and winter
  thrill-seekers.
•  Airstream Food Trailers: Serving elevated comfort and ski lodge fare such as hearty
  soups, grilled cheese sandwiches, tacos, and indulgent sweets like Belgian waffles, hot cocoa, and freshly baked goods.

Take a photo for Charlestown Bridge of Joy’s Photo Contest

Take a closer look at the grand prize for the Bridge of Joy Photo Contest – it’s pretty cool! A 12 inch blue painted bronze octopus by @gillieandmarcart If you’ve photographed the Bridge of Joy sculptures across the Navy Yard anytime since their arrival in August 2025, those photos count. New photos are welcome too. Deadline is February 17, 2026!

How to enter:
• Photograph any Bridge of Joy sculpture
• Post from a public account
• Tag @navyyardgarden
• Use #bridgeofjoycontest in your caption
• Enter up to 5 photos

BONUS: Shuffle over to Park-9 Dog Bar in Everett for their third annual CountryFest

Get your boots and hat ready to join Park-9 on Saturday, January 31st 5PM-10PM for good music, good food, red solo cup specialty cocktails and all the hoedown showdown fun you could want. Bring your pup – or come solo! Live Country Music by @anniebrobst from 6–9 PM

SPORTS!

Bruins vs. Lightning – Sunday, February 1st at 6:30pm

Celtics vs. Kings – Friday, January 30th at 7:30pm

Celtics vs. Bucks – Sunday, February 1st at 3:30pm

One week till the Super Bowl!! Check out how to make your Super Bowl Party memorable here!

Here are 9 places to watch the game in the neighborhood!

Check back as this list may be updated!