Boston Born: Olives & Grace & Everything Nice

Everybody and everything is online these days, but some things still require a more personal touch. A human touch. That’s the most important takeaway you can get from Olives & Grace and its owner, Sofi Madison.

A tiny subterranean shop filled with a menagerie of handcrafted, artisan products and food, the South End’s Olives & Grace has made a name for itself as the city’s go-to for stunningly crafted, sometimes humorous, and always thoughtful presents. Named Boston’s best gift store by local media several times over its five years on Tremont Street, the store’s story actually began in the Bay Area, before heading to the Bay State.

Olives & Grace’s South End store is celebrating its fifth birthday this month. That’s five years of endearing sidewalk displays, witty chalkboards, and funny cards.

“I was living out in San Francisco, and was really inspired by all of the artists and food makers and gift makers, and I just really wanted to create one space for them to be in,” Madison says.

Olives & Grace began online, Madison says, with a lot of corporate clients. She recounts quickly realizing that a brick and mortar store was going to be the right way forward.

“It wasn’t really until I could show them the product, and have them feel it that they could really see the level of quality, and the difference between a specialty brand and a mass produced one,” she says. “I think there’s a lot in that texture.”

“Some people gravitate towards the local scene, and that’s really cool,” says Madison. “I don’t discriminate about where products are from, I just care that it’s made by a small, small business.”

That texture that a handcrafted product comes with — the process, the care, the craftsmanship — its importance is most emphasized when Madison mentions Ajiri Tea, one of the products that has been in the store the longest. Beyond the quality tea itself, the packaging is handcrafted and illustrated by the women of the Kenyan tribe it comes from, on local banana tree bark that they peel themselves. The men harvest the tea, and 100 percent of the profits go back to educating orphans from those tribes.

“The fact that there’s so much more to it, that wouldn’t necessarily sell online,” Madison says. “But once you get somebody to talk to you about that brand, and you look at how beautiful it is and you try the tea, that’s the brick and mortar experience — it’s to really engage.”

“I never want to not be there,” Madison says of her small store. Most days of the week she can be found inside, chatting with regulars, building gift boxes, and spreading good vibes.

To be in the store, educating customers about the products, swapping stories, and chatting with local friends is Madison’s favourite part of the job, but that in-person engagement has been one of the largest parts of the store’s success.

“When you’re looking at someone, you can kind of read what they maybe need to hear that day,” Madison says. “Are they looking to be inspired? Are they looking to be left alone, but maybe recommended one or two products? Do they have a sense of humor? Do they want a product that gives back? You can kind of gauge that.”

One of the benefits of being small is that the company can stay live to what’s going on in the world. For example, Madison attended the Women’s March in Washington D.C., and had products speaking to those experiences just a few weeks later.

The business is agile to what customers want to see sold in the store, too, whether it be more witty cards or less ceramics, from the live feedback they receive.

“When you get to know the folks who are walking through the door, you get to have a shop that represents your customer,” Madison says. “Over the last five years, the store has really turned into Olives & Grace and the South End businesses that it looks to support. This community is as much a part of our brand as our makers are.”

“The South End is a really grateful neighborhood,” Madison proudly says of her home. “As a neighborhood, we’re cleaning up the streets as we’re walking down them. That’s really special.”

Madison means this in the truest and sincerest way. She can actually name all of her mailmen — Chris, Sal, Joey, Ping, Frank, and Martin — and they each make frequent appearances on the shop’s Instagram Story, offering first takes on samples that may hit the shelves.

“Who better to ask than your Boston mailman?” asks Madison. “If it’s good, they’ll love it. And if it’s not good, they’ll love to tell you that it’s not good! When they don’t like something, it doesn’t make it into the store.”

“We know our customers and that’s so lucky,” Madison says. “They make us happy, and their dogs make us happy, and their kids make us happy.” Dog treats are always on hand at Olives & Grace for regulars – like Maggie here – and newcomers alike.

Mailmen are perhaps the perfect metaphor for what Olives & Grace is truly about at its core: a connection. When so many of us are craving a genuine one — to our purchases, to our food, to other people — instead of a WiFi one, maybe the best way to start is by taking a page out of Madison’s book: with a little humanity, and a gift.

The name for the store was based on the original concept of a picnic shop. “You’d get your olives, and your jam, and your cheese,” Madison says. “Then grace, you’d appreciate and learn about the makers who were responsible for putting all of those products together.”
Instead of picnic baskets, Olives & Grace now specializes in thoughtful gift boxes filled with products from their shelves. Fear not, there is still plenty of good food involved. Shelby Russell, Madison’s lieutenant, assembles a box for a customer at the checkout.


Yelp connects people to great local businesses, and in our Boston Born series, we’re sharing the stories behind some of the highest-rated, locally-owned biz in and around the city. Features researched, written and photographed by Lloyd Mallison. To read what Yelpers have to say about the featured biz, download the Yelp app.


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