Brilliant Earth

WHAT YOU’LL FIND: Ethically sourced, eco-friendly diamonds and fine jewelry.

REASON TO GO: For a stunning collection of engagement rings, wedding bands, and other baubles that combine luxury with sustainability. Every piece sold is ethically produced, and each diamond can be tracked from its origin to the final delivery.

27 Boylston St. Ste. 140, Chestnut Hill, brilliantearth.com

The Half Cookie

WHAT YOU’LL FIND: Baked up in Charlestown’s Foundation Kitchen, these unique, hand-rolled cookies are made in small batches with premium ingredients. Bonus points for gluten- and dairy-free treats.

REASON TO GO: Each cookie is truly Instagram-worthy—we’re particularly fond of the half-pound cookie, stuffed with another cookie. Or stop by to sample the Street’s exclusive: the Chocolate Matzo, a blend of toffee, chocolate-matzo-bark, and Maldon-sea-salt deliciousness.

Marine Layer. / Photo by Haley Abram

Marine Layer

WHAT YOU’LL FIND: Ultra-soft, coastal-inspired clothing for men and women made from more than a hundred custom fabrics.

REASON TO GO: Founded by Michael Natenshon after his girlfriend threw away his favorite shirt, the company has built a brand that embodies a seven-day weekend vibe. Plus, with a focus on sustainability through its “Re-Spun” clothing-recycling program, you can feel not only stylish but also ethically responsible in your soft tee.

Wheat

WHAT YOU’LL FIND: Founded by visionary duo Huw Collins and Molly Shaheen in York, Maine, this boutique is known for its curated collection of contemporary clothing and accessories for both men and women.

REASON TO GO: Beloved for its laid-back yet sophisticated ambiance, the store stocks its own Los Angeles–made collection, as well as highly sought-after brands such as Zimmermann, Agolde, Missoni, and Hunza G.

Bridgewater Chocolate

WHAT YOU’LL FIND: Calling all bonbon lovers! In August, Connecticut-based Bridgewater Chocolate brought its award-winning toffees, turtles (a.k.a. tortels), caramels, and more to the Street.

REASON TO GO: Since Swedish chef Erik Landegren founded the company in 1995, it’s been crafting indulgent European-quality chocolates that are not only tasty but also beautiful, perfect for gifting or treating yourself.

Mejuri. / Courtesy photo

Mejuri

WHAT YOU’LL FIND: Sleek jewelry designs featuring diamonds, gems, gold, and other precious metals, as well as ear-piercing services.

REASON TO GO: For a rotating array of baubles (new designs are released each week), not to mention personalized stacking advice on how to style the oodles of bracelets and rings on offer.

Van Leeuwen Ice Cream. / Courtesy photo

Van Leeuwen Ice Cream

WHAT YOU’LL FIND: Skipping the fake stuff like stabilizers and opting for only high-quality ingredients such as fresh milk, cream, cane sugar, and egg yolks, this New York import creates simple ice cream flavors—think honeycomb and Earl Grey tea—alongside innovative options like marionberry cheesecake and vegan strawberry shortcake. And it doesn’t skimp on vegan offerings, either, using cashew milk, coconut cream, and cocoa butter.

REASON TO GO: The ice cream is so good that it’s known to draw long lines at all of its locations across New York City.

Roller Rabbit. / Photo by Haley Abram

Roller Rabbit

WHAT YOU’LL FIND: The first Massachusetts location of Roller Rabbit stocks the complete line of cozy matching pajamas and stylish accessories for men, women, kids, and babies. And don’t miss an exclusive collection of clothing featuring iconic Boston symbols.

REASON TO GO: The whimsical designs are crafted to bring joy and playfulness to your wardrobe.

Onyx Boutique. / Photo by Lindsay Ahern

Onyx Boutique

WHAT YOU’LL FIND: After a successful pop-up in 2023, this woman-owned Portsmouth, New Hampshire, boutique will be a permanent gem at the Street. Owned by Kristen Beauvais, it offers a curated selection of trendy brands such as Staud, Smythe, Ganni, and C.T.Plage.

REASON TO GO: To get styled by Onyx’s knowledgeable, friendly staffers, who’ll help you sift through the racks to find a showstopping outfit for any occasion.

Chanel Fragrance and Beauty

WHAT YOU’LL FIND: A wide selection of the iconic brand’s luxury cosmetics, skin care, and signature scents.

REASON TO GO: Because now you don’t have to schlep down to Newbury Street to get your Chanel fix.

SweatHouz. / Courtesy photo

SweatHouz

WHAT YOU’LL FIND: A customized cold-plunge experience, plus a bespoke infrared sauna and a post-sweat Vitamin C shower from the comfort of your
own private suite.

REASON TO GO: After your full-body treatment, you can treat your tresses to a high-level DIY blowout with the Dyson tools in the beauty bar.

Lymbr. / Courtesy photo

Lymbr (Coming soon)

WHAT YOU’LL FIND: Personalized stretching sessions that promise to improve flexibility, relieve tension and soreness, and enhance overall well-being.

REASON TO GO: Expert therapists tailor each session to your unique needs, promoting muscle recovery and relaxation.

Photo via The Street Chestnut Hill

From Then to Wow

A timeline of how the Street came to be.

1950

The Chestnut Hill Shopping Center is unveiled just 6 miles from Boston. The strip-mall-style center—considered the height of modernity because it featured air conditioning—quickly becomes a go-to destination for the community.

1970s–1990s

As the decades roll on, the shopping center grows and evolves, adding more stores and amenities to meet the needs of the surrounding community. Some renovations are made when the once-cutting-edge strip mall begins to show signs of wear, but the overall design of the complex remains the same.

2000s

WS Development becomes involved with the property, with a vision for a more-modern, mixed-use space. The journey begins with the transformation of the old Star Market into an elevated Star Market with additional ground-floor retail, setting the stage for future development.

2012–2014

This period brings significant construction, including a new three-story building at 33 Boylston Street that introduces a mix of retail, restaurants (Shake Shack’s first Massachusetts location), and office space, plus a new name: The Street. The reconstruction of 55 Boylston Street ups the ante even further with the addition of a new high-end theater (Showcase SuperLux).

2014

The Street’s makeover earns a Gold Award from the International Council of Shopping Centers.

Photo via The Street Chestnut Hill

Photo via The Street Chestnut Hill

2016

The unveiling of Curtis Kulig’s 99% Happy, a nearly 55-foot-tall art installation, adds some creative flair to the Street. The complex’s pop-up storefront concept also begins, adding local homegrown businesses like Legit, an athleisure-wear boutique that eventually becomes a permanent fixture.

2018

Legal Sea Foods (which opened its second-ever location in Chestnut Hill in 1975) relocates to a new two-story venue, paving the way for future tenants Warby Parker (2020) and Nike Well Collective (2021).

Photo via The Street Chestnut Hill

2022

Hummingbird Books, a woman-owned local bookstore, opens in April, enriching the area’s cultural fabric with a giant storybook treehouse that kids flock to after school, as well as many free author events for both children and adults to enjoy.

2023

John Guthrie’s Hope sculpture in front of the Nike Well Collective store becomes a new artistic landmark.

Photo via The Street Chestnut Hill

2024

The latest addition, a multi-tenant building at 27 Boylston Street (formerly the Container Store and, before that, a Filene’s department store), opens, featuring new retail, restaurant, and office space. The development as a whole now includes six distinct buildings with more than 400,000 square feet of space.

First published in the print edition of Boston magazine’s October 2024 issue with the headline, “Retail Revolution.”