Weekend to the Berkshires Travel Guide: Eating Edition
Life up here in the Berkshires is alluring – you wouldn’t be headed this way if it weren’t. But boy is there a lot of space between destinations up here. Almost three quarters of the Berkshires is forest, so if you’re driving out to a restaurant, a ski mountain, or The Pass Berkshires of course, you want to make sure it is worth the drive. Therefore, we’ve made a must-hit list of restaurants to dine at on your trip to The Pass Berkshires, to ensure your adventure is well worth the drive.
Restaurants in Great Barrington
Voted one of the most charming small towns in the country by several high-profile outlets like USA Today, Vogue, and Smithsonian Magazine, GB (Great Barrington) has become a truly acclaimed destination over the past decade. All that being said, none of these magazines know GB like we do, so here’s our suggestions for places to eat on your way to The Pass:
Great Barrington Bagel Company
Our pick for the best, most convenient breakfast (and lunch) spot in GB has to be Great Barrington Bagel Company. A staple to the community, this Bagel shop has been waking up in the wee hours of the morning to make fresh bagels daily for 3 decades. Their longevity in this area comes down to a few things. First and foremost, their NYC-style bagels are dynamite. With a plethora of cream cheese and toppings options, Great Barrington Bagel Company has dominated the breakfast sandwich market in GB.
No Comply
No Comply has hit the Great Barrington scene running. Staying true to its skateboard trick inspired name, No Comply doesn’t heed the typical upscale restaurant expectations. This bus your own table restaurant offers a unique, changing menu with a host of pop-in chefs and special events and themes to keep the atmosphere and offerings fresh. Most importantly, their food rocks. Between a weekend-only brunch menu and their Wednesday through Saturday dinner menu, you’re bound to have a cool, satiating time at No Comply.
Restaurants in Canaan
Our neighboring town of Canaan, Connecticut is nearly just as small of a town as we are. But just because they’re a small town doesn’t mean they don’t have dining options to offer. Canaan is the gateway into the Berkshires for those of you coming from Torrington, Winsted, Danbury, and other southwestern CT areas, so if you’re feeling peckish on your way through, here are a couple of options:
Blackberry River Bistro
Blackberry River Bistro sits unassumingly on the corner of the street right over the border of Connecticut. This small cornerside restaurant is run by a husband and wife duo, serving up some seriously good eats for dinner. Blackberry River is first come first serve, made-to-order, from scratch dinners, and is dine-in or takeout. If you’re on your way through Canaan (up to The Pass), Blackberry River Bistro is certainly worth a stop.
Ilse Coffee
Ilse Coffee has been a welcome sight to Canaan, renovating an old town garage into a chic, yet warm cafe. They isn’t all show though, they meticulously source their beans from growers across the world to ensure they are both ethically sourcing their products, while also upholding their high standards for good coffee. They also have guest bakers and chefs making sweet and savory treats as well, making a visit more than just a cup of joe. Any morning or daytime drive out to The Pass should be accompanied by a visit to Ilse Coffee.
Restaurants in Eastern New York
Our friends to the west host plenty of tourist attractions like Catamount Ski Resort or the beautiful Copake Lake area. But where can you grab a bite on your way in? Here are a few options to stop in on your way in on Route 23.
Willa
Millerton is an awesome little town on the border of Connecticut, with Route 44 heading straight up our way. Many of our customers who come up from the city surely know the town’s charm. Right on the main strip in Millerton sits Willa, an upscale dine-in restaurant that emphasizes their locally sourced ingredients. Willa’s commitment to responsibly and diligently sourced ingredients shows through their fresh, delectable meals.
Zinnia’s Dinette
Zinnia’s Dinette is the most unique recommendation on this list. They describe themselves aptly as a “New England fish fry with Hudson Valley Style.” This cool and colorful former diner offers some killer fried (and some not fried) fish dishes, plus a huge array of the best tinned fish you can get. You’ll find nowhere like Zinnia’s Dinette anywhere else in the region, so if you have a hankering for seafood on your way to The Pass, you know where to start.
Tommy B’s Pizza Joint
We’re not one to shy away from a pizza recommendation. We are unburdened by the politics of a New Haven or New York pizza scene, so we don’t mind telling you our favorites. Tommy B’s is a no-fuss New York style pizza joint serving up fresh slices. If you’re a fan of that classic pizzeria vibe and you like that crispy and cheesy pie, Tommy B’s is the place to be. More of a Sicilian style fan? Well, they have that too! Anyone coming into Massachusetts on Route 23 should stop by Tommy B’s Pizza Joint.
Restaurants in Egremont
Nobody rivals our quiet small town charm quite like Egremont does. As the buffer town between New York and us, there are some pretty neat stops for visitors from our neighboring state. Aside from scenic views and beautiful trailways, Egremont does have some pretty elite food options for a town of its size.
Hy’s Fried
Speaking of cool, modern spots in the area, Hy’s Fried is serving up some of the best chicken in the area, along with music and dancing every Saturday. Encased in an unassuming building just down the road from Catamount Ski Resort, sits the stylish and retro red interior of Hy’s Fried. What should you get when you stop in at Hy’s Fried? The fried chicken, of course!
Hilltown
If you’re looking for the best slice around, may we suggest Hilltown Hot Pies, just a few minutes away in Egremont. The anticipation for this upscale pizza joint to reopen was palpable, and they have not disappointed. Owner Rafi Bildner has a storied and impressive culinary history, learning from some greats around the country, and all that experience has settled in Egremont in a pretty special place. Stop in to select your Italian-style pie, and we promise you’ll be coming back for more.
Visit The Pass in the Berkshires
We are so lucky to be tucked away in such a beautiful part of this world. It makes it all the better that we have all these great restaurants near us. The Southern Berkshires is our home, and we want to share its pleasures with everyone, so make sure you make your trip to our dispensary worth the drive. Shop local, eat local, smoke local. You won’t regret it!