This guide is brought to you in partnership with Farnsworth Cannabis.
Just a short drive from New York City, Massachusetts’ famed Berkshires are the perfect summer getaway destination. The natural beauty, cultural offerings, and fine food are hard to beat. And, of course, there’s the legal weed.
This three-day itinerary—because why wouldn’t you take the day off?—is a blueprint for a successful summer weekend. But don’t let us restrain you—mix, match, skip, and add to it as the mood strikes. And honestly, there’s nothing wrong with not doing any of the below and just hanging around for three days straight.
First, you need a place to stay. While there’s a plethora of uniquehouses to choose from on Airbnb, there’s also some great hotels in the area. The newly opened Life House in Lenox is a great spot to get away from it all, whereas The Barrington will put you right in the heart of Great Barrington.
Now that you’ve got your accommodations squared away, you’re going to need some weed. Head over to Farnsworth Fine Cannabis in Great Barrington to secure some weekend fun in one of the most beautifully designed dispensaries in the country. We highly recommend their house brand cigarettes, which are wrapped with organic hemp paper, feature luxurious 32 mm-long filters, and are available in three proprietary effects that will match any of your moods: Light for a bright and heady lift, Classic for buzzy bliss, and Bold for full-bodied relief. While you’re there, mention Gossamer to any one of their knowledgeable staffers, and get The Farnsworth Flight (a single of each) for $30.
While in town, take a minute to pick up some food for the weekend. At Rubiner’s cheesemongers you’ll find a vast array of yes, cheese, but also fresh baked bread, charcuterie, and other fancy goods you can get in the city but want to eat up here. Keep going to Railroad Street for a little shopping. Pick up some music at one of the best record stores in the country, Rob’s Records, or some crystals to ward off bad vibes at the metaphysical supply shop Crystal Essence. You can also stop in at bookstore and gallery space Familiar Trees, which, despite the name, is actually relatively new. For lunch, grab some sourdough pizza from Baba Louie’s and then treat yourself to a little Soco Creamery ice cream because it’s probably hot and you’re beyond city limits where calories don’t count.
Once you’ve had your fill, head due north to Pittsfield, the biggest city in the area. If you’re a literature fan or just really into whaling, check out Herman Melville's Arrowhead house where the author penned Moby Dick.
Nearby is Wahconah Park, home of the Pittsfield Suns baseball team, and the perfect excuse for trying your Farnsworth Classic. Being high and attending a summer league baseball game is like a top ten American experience in our book, but your call. Plus more ice cream, and this time served in a little miniature baseball helmet. The great thing about baseball is that you don’t need to stay for the whole game, so head out whenever the mood strikes.
In case you need someone’s permission, let yourself sleep in—you’ve earned it.
Once you’re up, make your way to Lenox. Residents have ranged from Andrew Carnegie to Edith Wharton to more recently James Taylor. First, grab some coffee and maybe a little breakfast at Haven on Franklin Street. The pace might be a little slower than you’re used to, but that’s fine, right? You have nowhere to be.
Speaking of Edith Wharton, one local highlight is The Mount, Wharton's home-turned-National Historic Landmark. Even if you’re not a fan of the author, the estate is a wonder and there are lots of rooms and areas that are great for a good ponder (high or sober).
From there, we recommend checking out SculptureNow. There you’ll find the newly opened 2022 exhibition featuring 30 outdoor sculptures, including a botanical fainting couch and a rad blue land serpent (you’ll see). Light up the aptly named Farnsworth Light and stay as long or as short as you like.
For dinner, there’s pizza and small bites at Brava if you’re feeling more low-key, or the Mediterranean-focused Alta if you’re feeling high-key. Just don’t spend too long at either as your last visit of the day will be to Lenox’s famous Tanglewood outdoor music venue. If weather permits, grab tickets on the lawn. Make sure to bring a picnic blanket, some mosquito repellent, and at least one of those Farnsworth cigarettes. This summer’s performances include the Black Crowes, John Williams, and Van Morrison.
Good morning! It’s your last day here, so it’s time to be bold. Specifically with Farnsworth’s Bold cigarettes.
It wouldn’t be a complete trip to the Berkshires without a stop at Joe’s Diner in Lee. While it’s unlikely you’ve eaten there before, you’ve almost certainly seen this famous Norman Rockwell painting of a cop (probably verbally harassing a kid) in that very diner.
Once you’ve gotten your nostalgia for an America that never actually existed out of your system, make your way to Stockbridge. There, you can choose to see more Rockwell paintings at the aptly named Norman Rockwell Museum, or visit the historic Naumkeag. Originally home to famed lawyer Joseph Hodges Choate, the Gilded Age estate features beautiful gardens and a Stanford White-designed 44-room Shingle House. It’s one of those things that you can really get lost in, especially when stoned.
Speaking of weed, if you’re going to stock up for your trip home (note: we are not suggesting you do, but if you want to), take a trip back to Farnsworth in Great Barrington. After you do, grab a bite at Prairie Whale. The farm-to-table restaurant has become a must-visit in the area since opening in 2012, and makes a perfect finish to your long, but still too short, weekend in the Berkshires.