Live from the Grove at the Lawn on D, Harpoon Brewing put on the first-ever Boston Chilling Music Festival on Saturday, a free concert hosted by WBZ’s Matt Shearer. The event was designed to fill the live music-shaped hole left by Boston Calling’s announcement last June that it would not return for the 2026 season.

“[Harpoon] figured, ‘Hey, why not give people something to look forward to?” said Shearer. “And it’s all paid for by Harpoon, so anyone can just show up – which is a hell of a lot cheaper than Boston Calling.”

Host Matt Shearer

Boston Chilling featured the Lawn’s signature yard games, food and beverage, and a lineup of local-ish musicians, including Laundry Day, Lily Fitts, TOLEDO, and Ali McGuirk, with a DJ set by Lightfoot.

The crowd was electric, a diverse mix of Bostonians, including people coming from Pride, families looking for a way to spend the afternoon, and folks from around town rolling in for the music. Though undoubtedly smaller than Boston Calling, the new festival’s relaxed tone and open-space setting made Boston Chilling a more accessible live music experience than the traditional festival or club scene.

“The music and entertainment was top-notch, but by far the best part was all of the people involved. Everyone on the team made us feel comfortable and taken care of off the bat. We left feeling proud to be New Englanders,” said TOLEDO’s Daniel Alvarez de Toledo and Jordan Dunn-Pilz.

Ali McGuirk

McGuirk added that she has seen Boston change so much since she left six years ago. Her pals have all been priced out to Cambridge and Somerville, and many of the city’s iconic music venues have had to close their doors. Nonetheless, she still considers the city her home and enjoyed the opportunity to perform in front of old friends and family.

“Live music is so important in the city, and I think events like this show how badly the people need live music and how much they value live music,” Shearer said. “I think this is an opportunity for the city to look at what we’re doing and say, “We need to do more things like this.”

Hot off the heels of his first-ever live show, Shearer brought his trademark shenanigans and coterie of local celebrity guests to the stage with him. He was joined by “Love on the Spectrum” star and MBTA superfan Pari Kim for a Masked Singer- styled game lovingly titled “The Masked Singah.” Later in the evening, the East Boston queen of apartment tours, Benjamin Smith, would participate in “Are You Smarter Than a Boston Influencer,” where his knowledge of the neighborhood was tested.

“Always good to hang with Matt,” Smith said. “Great vibes throughout, and it was interesting to see local bands perform.”

This festival marked the opening of The Grove, a dynamic urban botanical venue featuring lush greenery, vendors, cabanas, and a packed schedule of summer events.

“We are ecstatic for this next iteration of the Lawn on D and can’t wait to welcome guests to The Grove this summer,” said Kristen Bonish, General Manager for Rebel Restaurants at the Lawn on D. “Reconnecting Bostonians in a fresh, beautiful, and innovative way with a space that has become synonymous with community is an honor. The Grove at the Lawn on D will be THE place to be in Boston this summer.”

The Lawn will host events all summer long, with special Fan Zone screenings of the World Cup scheduled for the coming weeks.