
Shop, pot & chill: Greater Boston spots for more than simply splurging (but for that too)
Every year around this time, we share the same collective thought ’round the Dig editorial table: Do people really need us to tell them where to shop? Again?
And then we all inevitably rediscover what a shithouse disaster the internet is, and consider how it has become an unnavigable mess that serves marketers first and consumers last.
That’s especially the case if you hope to shop locally. You may find some killer past compendiums from the Dig and the other remaining regional outlets that give a shit, but mostly your searches will direct you to spammy scam listicles spun out by algorithms.
Furthermore, things change. Particularly in pandemic times. We’re pleased to report that many of our beloved staples are still open for business, and in some cases have even been joined by new kids on the block, some of which are cannabis dispensaries duly noted herein.
Whether you need a reminder and recalibration of your shopping radar or are new around these sections and want to be steered away from mass-market dumpsters, here’s our abridged road map of recommendations for this holiday season …

Coolidge Corner (Brookline)
Somehow, the parking in Coolidge Corner isn’t nearly as awful as you would expect it to be. Or of course you can slide right in on the Green Line. Simple logistics aside, this is simply one of the most concentrated areas for inspired commerce and culture plus grub, weed, and more, the sort of square that resembles a black-and-white photo of worry-free American shopping before customers trampled each other to death over plasmas.
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Shop: Don’t forget to grab something made of leather or latex at Good Vibrations, then pick up for every music geek in your posse at Village Vinyl & Hi-Fi, and maybe get eclectic at the legendary Fire Opal (artsy clothing, interesting jewelry). With those and several other worthy options, you may want to save Brookline Booksmith for last so that you don’t have to haul around two armfuls of hardcovers (some signed, if you’re lucky) that you’ll inevitably leave with.
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Pot: For cannabis, you’re within walking distance of Sanctuary Medicinals, a rare dispensary where you will find a whole bunch of the store’s namesake products for sale. That means the sales staffers know their stuff, and can walk you through a whirlwind of exceptional house items ranging from proprietary vape carts to their game-changing slow-roasting DABado DabTabs.
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Chill: What’s your mood? Whether beer (Hops N Scotch, Coolidge Clubhouse), outstanding Chinese (Dumpling Daughter), or Mexican (Los Amigos Taqueria), you’re covered.
Union Square (Somerville)
If you read the Dig on the regular, then you know we adore Union Square and Bow Market within it. The latter all alone is a place where you can easily frolic for hours in non-holiday times, from the sweet variety of suds at Remnant Brewing to the various one-off events hosted by Bow, some in coordination with our friends at Union Square Main Streets. Heading into the busiest time of year, there will be even more bells, whistles, and vendors in the mix than usual, plus more than a dozen other stores to visit outside of the market.
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Shop: Short of shouting out every last unique small biz inside Bow, we figure that in a world of hellish retail entities like Target shouting, simply naming a few stores with monikers like Vinyl Index, Blue Bandana Relics, and Tiny Turns Paperie should be enough to lure anyone who still has yet to pay a visit. And that’s just inside Bow; beyond the courtyard, at the very least be sure to flip through a few boxes of books at Hub Comics and stacks at Somerville Grooves.
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Pot: You’ll need a medical card to shop at Liberty Cannabis, but if you have one, we really recommend this spot. It’s sleek and quaint and features an outstanding selection of concentrates and edibles, including top brands like the Heirloom Collective as well as their own picks.
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Chill: If you want to chill-chill—like, really hang out for a bit and contemplate your purchases—you have some options: Bloc Cafe for java, Sally O’Brien’s or the Independent for a lager, others. But if you’re done looking around and want to tie a bow around the afternoon, a meal at Juliet is a gift unto itself.
Central Square (Cambridge)
One great thing about Central Square is that you won’t encounter many snobs there. You’re laughing—Cambridge is among the most elite cultural enclaves on earth, a technologically hip liberal playpen for cycling literati in designer rags. But we mean it about Central; thanks in part to the centers and services that help out Cambridge community members who powerful universities step on, the area still has an edge, which has only been sharpened by the unbelievable work of the Central Square Business Improvement District. If you’re heading to this area for a holiday haul, we recommend starting or ending with the micro vendors in their recurring Popportunity Market and Starlight Square events, then hunting in either direction down Mass Ave from there.
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Shop: Unlike some other squares that are just finding their identities and landing tenants in the past few years, over several decades Central has cultivated the iconic likes of Cheapo Records and Seven Stars bookstore, and more recently welcomed newcomers like Cleenland (low-waste home supplies) and Lola’s (kickass vintage).
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Pot: Similar to Union Square in Somerville, you’ll need a medical card in Central. But if you have one, you’re welcome in Revolutionary Clinics in the heart of it all.
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Chill: From A4cade, to the Middle East, to our longtime loves at Veggie Galaxy, you can drink and dine for days at a time between scoring gifts around Central. Or, if you don’t want to chill, get some ink at Lucky’s, which has a unique jewelry boutique as well.
Centre Street (Jamaica Plain)
Jamaica Plain had better be the best of destinations, because unless you live in neighboring Roslindale, Hyde Park, Brookline, or Mission Hill, you have to take a day off of work to access the heart of this natural cultural concourse, properly browse all the shops, and make it out before the Orange Line, 39 Bus, and J-Way all start to resemble rush hour on Snowpiercer‘s supertrain. We encourage you to walk Centre Street and to also pay attention to the South Street stretch between Forest Hills station and the Civil War monument.
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Shop: Though there are some longtime survivors in this area, and new shops that reflect beloved old ones, what’s important is that there is lots to check out, from the always-reliable women’s store Susanna to the gem of all gems, internationally-flavored but neighborhood-minded milliner Salmagundi.
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Pot: This is where you really luck out, and you’d better put some extra time aside. Inside the Seed dispensary, you will also find an interactive Core Social Justice Cannabis Museum where you’ll learn lots about the history of weed in America to chatter about when you’re stoned later on.
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Chill: There are dozens of places for great drinks and grub between shops, but since you’re on a shopping mission we recommend Tres Gatos, Boston’s “first full-service restaurant, book, and music store” and a one-stop-shop near-and-dear to our stomachs and hearts.
Grove Hall (Dorchester)
There are any number of squares, corners, and corridors in Boston’s biggest borough where you could easily burn all your holiday cash while adding on pounds with great eats, from athletic gear and local art in Fields Corner to the refinished South Bay, which we actually love some things about (Carhartt is our heart). We popped into the Grove Hall Mecca because while there aren’t too many retail shops, the area itself comprises the geographic heart of the city along with Nubian Square and is a unique juncture of crisscrossing cultures and nonstop pedestrian action.
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Shop: While they’re not a locally based company, one round at this or any other Madrag will cover all of the youngs in your family combined. While you’re at it, knock over to Rainbow, which always has ridiculous deals (though not always in the common sizes), and you’ll likely score for some of your more Instagrammable cousins and friends.
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Pot: Let us never forget that when it comes to recreational dispensaries in Boston proper, Pure Oasis came first. That’s brought with it a lot of responsibility, all of which the crew there has competently managed. Also don’t forget that cannabis makes for awesome gifts, and the team greeting you in Grove Hall has the experience to guide you toward proper stocking stuffers for the stoners in your life.
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Chill: Though there are some choice bites to grab on the go outside of the Mecca (be sure to stop by La Cuchara on Blue Hill Ave for Dominican food), for a proper sit-down slide a bit farther down to Merengue. Once you’re there, order everything on the menu starting with the mariscos a la plancha grilled seafood combo.
Dig Staff means this article was a collaborative effort. Teamwork, as we like to call it.