If you have lived here more than a season, you already know the sound: a Thursday morning on The Green at 33 Boylston, a toddler class in one corner, a barre3 mat unrolling in another, and the low rumble of the D branch of the Green Line pulling past the trees behind the parking deck. What is different this summer is how much of Chestnut Hill's daily life has migrated outdoors, and how little of it now requires a car once you are here.
The story you have probably read about The Street this year is a retail story: new tenants, new mural, new building at 27 Boylston. That is the surface. The real change, for people who actually live within walking distance, is that the outdoor room between the shops and the reservation has quietly become the neighborhood's most-used public space. This post is about how to use it.
The Green is doing what a town common used to do
Summertime at The Street, the free programming series that anchors The Green from late May through the end of August, is not new. What is new is its density. On Thursdays, The Street Chestnut Hill hosts The Street Tots on The Green from May 29 through August 28, with musical performances, dance, magic shows, and story time. Fridays bring live outdoor music once a month from So Good Sounds, a women-owned booking business that places local musicians on The Green from 5:30 to 7:30 p.m. on June 9, July 14, and August 11. Saturdays and select weekdays cycle through Street Sweat classes in partnership with lululemon, Arc'teryx, barre3, and other health and wellness partners, offered free on select dates throughout the summer.
Then there is the dog contingent. Yappy Hours run 5:30 to 7:30 p.m. on June 14, July 19, and August 23, with live entertainment, dog treats, and toys on The Green. If your calendar reads July 19, that is the summer's midpoint Yappy Hour, and Polkadog Bakery is running its own Dog Days series alongside it, including a custom personalized dog bandana session with STITCH(ed) Needham on Sunday, July 20, with tickets at $15 that include a Polkadog treat bag and a pup cup from The Half Cookie. If you have been here five summers, you have watched this programming grow from a few pop-ups into something closer to a shared calendar.
What actually just opened, and what is still coming
The retail turnover at 27 Boylston is easier to track as a table than a paragraph. Here is where things stand for the back half of 2026:
| Tenant | Status | Notable detail |
|---|---|---|
| Birkenstock | Open since January 2026 | 15th company-owned US store, opened as the brand approaches the 50-year milestone of its Boston clog in 2026 |
| Mejuri | Open | 1,326 sq ft "first edition" of a new 3.0 store design with a redesigned Ring Bar and full-service piercing studio |
| Bridgewater Chocolate | Open | New England confection maker, first Chestnut Hill location |
| Pink Carrot | Open | Local, health-forward, woman-owned café with a debut kids' menu |
| Winston Flowers | Open (redesigned) | Rebuilt Chestnut Hill location of the local florist |
| M.M.LaFleur | Recently opened | Women's workwear brand |
| Brilliant Earth | Open | First try-on bar with interactive stations for engagement rings |
| Boll & Branch | Opening 2026 | First-ever Massachusetts location at The Street, Suite 33-40 |
| The RealReal | Late 2026 | First Massachusetts brick-and-mortar, at 27 Boylston Suite 27-210, next to Birkenstock |
Read down that column and the pattern is not "another luxury mall." It is a lot of first-Massachusetts locations landing at once, plus locally rooted operators like Winston Flowers, Polkadog, and Pink Carrot getting more square footage or new formats. For a resident, the practical effect is that a Saturday errand loop that used to require Newton Centre, Coolidge Corner, and a florist stop in the South End now largely happens between two parking decks. Whether you want that consolidation is a separate question. It is happening either way.
Overhead of all of this is Agostino Iacurci's "Tall Flowers," a 40-foot-tall mural on the second and third-story facade of 27 Boylston, inspired by the Chestnut Hill neighborhood and its natural surroundings. It faces Route 9 and reads best from the sidewalk in front of the Bloomingdale's side of the property, not from a car window.
The back door most people forget
The reason The Street works as an outdoor room, and not just an outdoor mall, is what sits directly behind it. The Street is located alongside the largest conservation area in Newton, Hammond Pond Reservation, a family and dog-friendly reservation with dozens of walking trails including a 2-mile loop, used for walking, jogging, birding, rock climbing, and cross-country skiing. The DCR parking lot is on the left as you enter The Street from Hammond Pond Parkway, and it is free.
In 2021, the Newton Conservators marked the reservation and the adjacent Webster Conservation Area with a color-coded loop system that most people who parked here for shopping have never noticed. The three loops:
- Blue Trail — Access from the DCR Hammond Pond Reservation lot behind The Street, past a popular rock-climbing cliff. Roughly the pondside route.
- Green Trail — Runs the far side of the MBTA tracks through Webster Woods, passing Gooch's Cave and Cake Rock.
- Red Trail — From the DCR parking lot, past Cat Pond, a small vernal pool, to Bare Pond, a larger vernal pool.
The three color-coded loops range from 0.8 to 1.4 miles, and longer walks are possible by combining two or three routes. That is the piece most residents miss: you can stitch a Blue-Green combination into a 45-minute evening walk that leaves from a parking spot you were going to use anyway.
The reservation is also older and stranger than it looks. Its first parcel was acquired from John Lowell in 1916, and Hammond Pond is listed as a Massachusetts "Great Pond". The bouldering rocks along the Blue Trail are formations of sandstone conglomerate and Roxbury puddingstone, which is the state rock and which almost nowhere else in Greater Boston puts you within a five-minute walk of a Shake Shack.
A Thursday, actually mapped
For readers who prefer their neighborhood advice in wall-clock form, here is a template that a lot of long-time residents already run without saying so out loud:
- 9:30 a.m. — Coffee at Blue Bottle. If the kids are along, The Street Tots session on The Green starts mid-morning.
- 11:00 a.m. — Blue Trail loop from the DCR lot, roughly 40 to 55 minutes at a walking pace. Bring water; there are no food concessions inside the reservation.
- 12:30 p.m. — Lunch at Pink Carrot or a counter seat at Bianca, which is a modern American restaurant from James Beard Award winning chef Tim Cushman and Nancy Cushman, the team behind o ya and Hojoko.
- 5:30 p.m. — Yappy Hour on The Green on 7/19 or 8/23, or a So Good Sounds set on 7/14 or 8/11.
- After dinner — A slow Germantown-side lap past the "Tall Flowers" mural before the light goes.
You do not need to do all of it. The point is that this is the shape of the summer if you build it out of what is already free and already here.
What this summer is quietly saying
The through-line, if you stand back from the Yappy Hour flyers and the RealReal press releases, is that Chestnut Hill's outdoor infrastructure and its retail infrastructure are finally being programmed as a single space. The Street's transformation under WS Development earned a Gold Award for Renovations and Expansions of Mixed-Use Projects from the International Council of Shopping Centers, and it sits at 33 Boylston along Route 9 between Hammond Pond Parkway and Hammond Street. That framing, mixed-use rather than retail-only, is a useful one for residents too. The Green is where a village common would be if this neighborhood had grown up around one. Hammond Pond is the back garden. The 27 Boylston building is the storefront. It is the first summer that all three feel like they are meant to be used together.
If you have been telling out-of-town family they should drive over on a Sunday, that framing is probably how to do it now: the reservation first, the mural second, lunch third. In that order, it reads as a neighborhood. In reverse, it reads as a mall.
For a longer conversation about which pockets of Chestnut Hill sit closest to The Green, which sit closest to the Blue Trail trailhead, and how those two things shape what daily life looks like at your address, Eileen Strong O'Boy is happy to walk the neighborhood with you. Request a home valuation any time.
