Feel like you are being watched? Look up, because Winteractive is back for a third year

Local News

The 2026 Winteractive installations, large-scale outdoor art pieces spread out around downtown Boston, are being rolled out this week.

Have you seen the big blue eyes staring down on downtown Boston, or the tentacles unfurling from the windows of an empty building in Downtown Crossing? Or remember the ever-so-famous Mr. Pinks, the giant inflatable figures that clung to the buildings and trees of downtown Boston last winter?

Winteractive, the initiative behind the quirky downtown Boston installations, is returning for another season. 

“We devised Winteractive three years ago as an opportunity to kind of prod people out into public, throw on a jacket or extra layer of clothes, get your heated gloves, and be able to take in international quality level of public art exhibits,” said Micheal Nicolas, President of the Downtown Boston Alliance. 

Presented by the Downtown Boston Alliance, Winteractive installations have been popping up throughout the week. All told, the exhibits will feature work from artists from seven different countries and four continents. The outdoor art will be on display until March 29. 

Some of the most eye-catching installations so far are the gigantic, emoji-like eyeballs placed on top of buildings like the Brattle Book Shop and 151 Tremont St. The collection, called “Big Other,” is set to display six gigantic sets of eyes, five already up.

“We found it fun and whimsical. We like that it’s a series,” said Nichlos. 

One piece already installed in Downtown Crossing, Artificial Humans, features lifesize, glowing statues of people spaced out on the steps between the TJ Maxx and Old Navy. 

The statues, which are all staring down at their hands, are meant to encourage viewers to think about the use of AI and how the world is drawn to their devices, according to an artist’s statement.

Some Winteractive installations invite viewers to engage directly with the art, like the group of see-saws, titled e/motion, now stationed between the Macy’s and Primark in Downtown Crossing.

On Tuesday, Winteractive began inflating an installation of giant kraken arms. In past years, Winteractive has used inflatables in their work, like the Mr. Pink installation last year and a pair of floating clown heads the year before. 

It seems the use of inflatables will become a Winteractive tradition.

“Without promising this for eternity, it’s probably a pretty good guess that we would try to do a high profile inflatable each year, because they just seem to be something that captures people’s imagination,” Nichols said. 

The meaning behind these installations may teeter from real-world messages to lighthearted fun, but according to Nichols, the installations are meant to lift heads from phones to enjoy something different. 

“We are not trying to commit to any political viewport with them quite as much as to provoke conversation and introspection among the viewers,” Nichols said. 

As of Wednesday, there will be 15 art installations across Boston, with two more waiting in the wings.

The next installation is scheduled for Jan. 14 at the Financial District’s Winthrop Square. 

Named after John Winthrop, who recorded one of the first ever UFO sightings, the park will be welcoming Bo the Bison in his van. Bo is an alien enthusiast who has been travelling across the country to reach his destination at Winthrop Square. A rocket ship is already in Winthrop Square awaiting Bo. 

“It will be a wood sculpture of a larger than life Bison, who’s going to be sitting on the top of his camper van with a telescope looking for aliens,” said Nichols. 

While on the topic of UFOs, a space-themed Winteractive piece was damaged by a masked vandal in 2025.

“The stuff that is directly accessible has to be a bit more durable. We have to find ways to secure it, you know. People could jump on them, push them, tear them down, do whatever, on purpose, by accident, like you never know. We do try to be very mindful of where we place art, how valuable it is, how accessible it is to the public,” said Nichols.