The Street Chestnut Hill in October 2026: Changes and Events

"There are a million reasons why restaurants close, but this one is not closing because of lack of business," Steve DiFillippo told Boston Magazine in June. "We're closing because we don't have a lease. We can't stay in a space that's not ours."

Davio's Northern Italian Steakhouse served its last plates at 55 Boylston Street on June 28. That ended a run that began in 2013. Three months later, the reason for the closing tells you more about this fall at The Street than any opening does. The biggest changes along this part of Route 9 in 2026 have come from ownership and lease decisions made somewhere else. When a space goes quiet for that kind of reason, it tends to stay quiet longer than one that closed because business was slow.

The restaurant that shared a building with a movie palace

Davio's didn't have a typical storefront lease. The restaurant shared space with the Showcase SuperLux, and DiFillippo said its arrangement was with the theater. That arrangement ran out in June. By then the Showcase chain had been sold by Harbor Lights Entertainment, owned by Paramount's David Ellison, to the European theater company Kinepolis Group. DiFillippo said he had no deal with the new owners and learned the restaurant would close only about a week before announcing it.

That sale became official on September 11. Kinepolis announced it had finished buying 13 U.S. Showcase cinemas: seven in Massachusetts, four in New York, one in Ohio and one in Rhode Island. The company owns six of those buildings outright and runs the rest under leases. Two lines from that announcement matter most for anyone who lives near 55 Boylston:

"Kinepolis will continue to operate Showcase Cinemas under the existing brand name and prioritizes the continuity for all Showcase customers."

The second line comes from CEO Eddy Duquenne. He said the purchase "provides a valuable real estate position, with future opportunities for further redevelopment and optimization being explored." That comment covers all 13 theaters. It isn't a plan for Chestnut Hill. No one has publicly said what will go into the former Davio's space.

For now, the theater runs as before. Showcase's own site still lists it as Showcase SuperLux at 55 Boylston Street, with showtimes and online tickets. A Friday movie night still works. Dinner in the same building is the piece that's missing.

DiFillippo has said he's "looking for a new spot in Chestnut Hill." As of early October, he hasn't named an address, signed a lease or set an opening date. He also told Boston Magazine that most of the Chestnut Hill staff would move to other Davio's locations.

Two sit-down rooms gone, counters and shops in their place

Davio's was the second full-service dinner spot on this stretch to close this year. Limani, the Greek seafood restaurant at 33 Boylston Street, closed in January. The businesses that opened nearby since then run on a different model.

The Sweetish Fish is listed at the same street address as Limani. None of the coverage says whether the candy shop moved into the old restaurant's suite. Madras Dosa Co. is the Indian street-food brand's third Massachusetts location, after the Seaport and Cambridge. Both places are good for a quick stop on a Saturday errand loop. Neither replaces a reservation for a birthday dinner, and so far nothing announced for The Street fills that gap.

A retailer that came because the customers were already here

The RealReal's arrival is the clearest sign of what does fit The Street right now. On September 16 the luxury resale company said its first Massachusetts store would open October 15 at 27 Boylston Street, Suite 205. The 1,800-square-foot store will handle consignment, authentication and in-person shopping for women's and men's fashion, handbags, fine jewelry, watches and accessories.

The company said it picked the location "based in part on the strength of its existing community of buyers and consignors across Greater Boston." Chief Merchandising Officer Samantha McCandless said Chestnut Hill lets the company "meet them where they live, shop and spend their everyday lives." Put another way, the store is following customers it already has online in this area. It isn't betting on new foot traffic.

One caution on timing. As of September 21, The Street's own tenant page still listed The RealReal as "Coming Soon!" and was showing hiring posts from September. October 15 is the announced date, and the store hasn't opened yet.

LoveShackFancy, meanwhile, showed up on The Street's homepage with a "Shop Today" note by October 1. Every new arrival this year has been retail or a counter-service food spot.

What you can actually put on the calendar

The commercial side of Chestnut Hill is uncertain this fall. The events calendar isn't. The last weekend of October is the fullest of the season, and every item below has a confirmed date and time.

Thursday, October 22

Splendid at The Street is hosting a color-analysis evening from 6 to 8 p.m. All month, The Street is also running the Ellie Fund's "Turn Pink" campaign, which lets shoppers round up their purchase at participating stores as a donation, through October 31.

Saturday, October 24

Trick-or-Treat at The Street runs from 11 a.m. to 1 p.m. It's free and includes treats, costumed characters and family entertainment. If it rains, it moves to Sunday, October 25. If you're planning a costume and a lunch around it, check the forecast Friday night.

Sunday, October 25

Sunday works well split into two halves with a short drive between them.

1. Noon to 4 p.m., Longyear Museum Family Day, 400 Beacon Street. Free house tours, a horse-drawn carriage, crafts, period games and a food truck.
2. 2 to 3:30 p.m., "What Are Those Knobby Rocks?" with the Newton Conservators. This free geology walk in Webster Woods meets at 101 Hammond Pond Parkway. The rain date is Sunday, November 1.

The two events overlap. You can spend the early afternoon at Longyear and then head to Hammond Pond Parkway for the 2 p.m. start, or do the walk first and catch the last couple of hours of Family Day. If Saturday's trick-or-treat gets rained out, all three events fall on the same Sunday.

Looking ahead to November

Simon lists its Santa Photo Experience at The Shops at Chestnut Hill as opening November 20, with photos at Center Court through December 24. That's the first holiday event with a firm date so far. The Street's posted calendar currently runs only through the end of October.

The other change coming down Chestnut Hill Avenue

One more decision this fall will change how people move between Cleveland Circle and Route 9. In September, Brookline's Transportation Board voted unanimously for a redesign of Chestnut Hill Avenue between those two points. The plan adds a two-way protected cycle track, 65 parallel parking spaces and new crosswalks. In March, Brookline.News had reported the town was pumping the brakes on the plan, so the September vote put the project back on track. The Select Board could still review it if someone appeals. Construction was described as likely "in the spring," with no start date posted.

Taken together, the year looks like this along Boylston Street. One restaurant left because of a theater sale. A national retailer is arriving because, in its own words, its buyers and consignors are already here. The bike route will follow a town board vote. And the future of 55 Boylston depends on what Kinepolis decides about a building it now operates, with no public plan for the space as of October 4.

If you own a home near The Street and are wondering how changes at 55 Boylston, the new tenants along Route 9 or next spring's work on Chestnut Hill Avenue might affect your property's value, Eileen Strong O'Boy is happy to go through it with you, block by block. Request a Home Valuation, and we'll start with what's happening on your street this fall.