Taking the high road to Massachusetts’ cannabis capital


After so many months of sticking close to home, the summer of ’21 is road-tripping time, XXL. And if you’re looking for a destination nearby where you can buy and get high, you can’t really do better than Great Barrington. Between it and nearby Sheffield, you’ll find every kind of recreational cannabis for sale, all legal, less than a two-and-a-half-hour drive from Brooklyn—just don’t forget your cash or debit card as federal banking regs make credit cards a no-go.

For those of you wondering, “Why bother heading north, now that recreational marijuana is finally legal in New York State?” Well, we’re still likely years away from having dispensaries established for one thing. For another, of the 11 states with recreational dispensaries, Massachusetts is the only one within driving distance (unless you’d like to make the trek to Michigan). As such, it’s your best bet to experience what it feels like to both buy and consume cannabis above board for a few days. So, for now, it’s Great Barrington or bust for us.

Plus, with a handful of dispensaries lining this 4.3 mile strip between Sheffield and Great Barrington along Route 7/Main Street, it’s a straight shot to pot paradise. Not to mention, the drive itself is part of the trip, up the scenic, truck-free Taconic and over winding country backroads. Along Routes 44 and 41, you’ll roll past the horse farm-dotted hills of Millbrook, the 18th century church-lined streets of Sharon and Salisbury, Connecticut, past tweedy prep school campuses (Hotchkiss, The Berkshire School), and the gentle peaks of the Berkshires.

Arriving in Sheffield, the beginning of dispensary row, your biggest challenge is figuring out which shop is for you—each one has its own distinct vibe. Pick a candidate from the list below, pull into your preferred parking lot (noting all the NY and CT plates), do a pre-shop ID check at the front-desk, and let the cannabis shopping begin, curated by extremely knowledgeable (and adorably earnest) ‘bud-tenders’ determined to help find your perfect cannabis fit. May we recommend Betty’s Bedtime Eddies (an all-but-miraculous sleep aid combo of CBD, THC, and melatonin) or a Flying Bon Bon Dark Chocolate bar?

With your new-found stash, now it’s time to pull off the road and into a sweet little spot for a very relaxing overnight at 33 Main, the super luxe, very small boutique hotel created by a local design mogul Annie Selke, or go big at a legendary wellness nexus—like Canyon Ranch or Miraval—with hot stone massages and couture-level grub for every possible palette and dietary diversion.

Spend the better part of the next day lolling around the pool in a mild, THC-induced haze, or strolling the very cute shops along Great Barrington’s main drag. Clear the car of any left-over cannabis (transporting it across state lines is still illegal, folks), then hit the road and head south for 18 miles along Route 44, which leads straight into the sweet little hipster burg of Millerton, New York. Stop into the massive, but manageable, Millerton Antique Center to hunt for treasures, and stroll half a block downhill to grab a late lunch at the retro, upscale Oakhurst Diner—try the BLT with avocado or the Bahn Mi Roast Pork Sandwich—afterward, roll back into Gotham, relaxed and refreshed, long before sunset (and the Sunday scaries set in).

Get to know Great Barrington’s, Big 5 recreational cannabis dispensaries

The Pass Berkshires

1375 N. Main St., Sheffield, MA, 01257

If the license plates in the parking lot are any indication, proximity to the New York State line (seven miles) makes The Pass strategically ideal for both day-tripping, out-of-staters (despite the legal concerns) and locals living on the south end of Great Barrington who want to avoid weekend tourist traffic. Easy in, easy out, quick, pleasant, and legal, The Pass ticks all the boxes. Its knowledgeable bud-tenders will help steer you to a strain, edible, tincture, or oil with your name on it. If flower—the polite way to refer to weed—is your default, the house brand here tends to be very, very fresh as it’s grown right out back. But don’t get any ideas—security for the on-site ‘garden’ rivals Fort Knox.

Rebelle Dispensary

783 S. Main St., Great Barrington, MA, 01230

The mission at Rebelle, according to owner Charlotte Hanna, is to “change hearts and minds about this plant.” Which is why she focuses on transparency, including an open floor plan for her store. “Nothing is hidden behind counters,” she says. “The idea was to have people be able to just walk in and see all of the merchandise we have out on display and accessible.” The shop’s boutique-meets-spa vibe, think a sort of Kiehl’s of cannabis, makes for more tactile, interactive and “normal” retail experience. Customers can pick up the products, read the labels, and chat up the well-versed staff. Don’t miss Rebelle’s canni-bar display which features 15–20 strains of flower, each in its own sniffable container with built-in magnifying glass so aficionados can get an extra close look at the buds. So, what are New Yorkers buying? Says Hanna, who splits her time between Brooklyn and the Berkshires, “anxiety and sleep by far are the biggest drivers for New Yorkers that come in.” (Yup, that sounds about right.)

Calyx Berkshire Dispensary

307 Main St., Great Barrington, MA, 01230

You can’t miss Calyx, smack in the middle of Great Barrington’s main drag. Despite the in-your-face location, inside, the vibe is low key. The walls of the laid-back, women-owned shop are lined with product displays tucked into simple bookcases accented with cacti and spa rocks. Favorite product? Their “Buy Weed from Women” canvas tote. Best of all though, Calyx is just across the street from Robyn’s Candy—a delectably overstuffed sweets emporium that offers up one major munchies solution.

Farnsworth Fine Cannabis Company

126 Main St., Great Barrington, MA, 01230

If Schitt’s Creek’s Rose Apothecary got into the canni-biz, it would look like the charmingly twee recreational dispensary, where high design is everywhere on offer. From the freshly-painted blacktop in the parking lot to the eye-catching black-and-white storefront, and right on thru to the retail floor. Inside this serene cannabis atelier, the walls are lined in elegant oak cabinetry, displaying a selection of cannabis edibles, drinkables, tinctures, flower, accessories, and their own boxed Farnsworth cannabis filtered spliffs, rolled with organic paper—all presented like works of art in a downtown gallery and lit to dramatic effect. Stylishly dressed staff is on hand to assist the shopping experience. Plus canna-merch and gifts are also available, curated by, and in some cases, designed by, proprietors Alexander Farnsworth and Brooklyn-based fashion designer Adam Lippes.

Theory Wellness

394 Stockbridge Rd., Great Barrington, MA, 01230

The final and northernmost stop on the toking trail is Theory Wellness, the OG of the GB area, it being the first dispensary to open as a medical facility back in 2017. When recreational cannabis got the green light in 2019, Theory was ready and opened up in time for the stampede that 2020 brought with it. Outside, it’s a mild-mannered, New England-clapboard-style building. Step inside, though, and it’s a bustling beehive of cannabis sales, think Trader Joe’s minus the Hawaiian shirts, catering to a mixed crowd of locals and weekenders. Although the lines move quickly and efficiently, there’s no rush—the staff will take as much time as you need to answer any questions that come to mind. Even if you enter clueless, you’ll leave with thoughtfully chosen product.

The weekender’s cannabis shopping list

When it comes to flower, much like wine, each to their own. When it comes to edibles and drinkables though, there are a few reliable crowd-pleasers to consider which, with the exception of the house brands, are carried in most of the big five shops.

  • For the chicest pre-roll: Try Farnsworth’s boxed, filtered cannabis cigarettes, available in three strengths.
  • For social drinkers: Try a 6-pack of Cann’s Cranberry Sage Social Tonic ($24), a cannabis -infused seltzer, or Theory’s 4-pack house brand Hi-C in lemon/lime seltzer ($15).
  • For chocolate lovers: The Flying Bon Bon’s Milk Chocolate Bar ($16) is a creamy and indulgent after-dinner cannabis treat; it’s also available in dark chocolate, too.
  • For candy lovers: IncrEdibles gummies in watermelon are delish.

One Response

  1. Karl Tombstone -

    The people of MA passed MMJ and Adult use by ballot initiative because our politicians weren’t listening. We gave up waiting and wrote and passed our own laws. Then guess what? The politicians changed them! They apparently know better then us little people.
    Then it took years for the politicians to get their act together and open the first medical dispensary! It also took years for the first Adult use stores to start opening! And they still messed things up.
    Yes, timelines need to be included in the legislation, but shorter timelines. Force the politicians to do there jobs! Two different administrations dragged there feet enacting these laws.
    They still haven’t opened any businesses where Cannabis can be consumed on site. We voted for and passed this provision! It is the law! Yet nothing!
    As for the rollout, if you open 1 Cannabis store, in a state with 6 million people, and several states nearby…expect traffic!
    MA Cannabis is a joke. Unless you’re a multi millionaire or a big national company, don’t bother.
    And the weed is expensive and isn’t very good.
    We need more craft farmers and ways for the farmers to sell their products.


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