Our Favorite Berkshire Wineries, Breweries, and More!

Apple picking, hiking, soaking up the cool, crisp mountain air… What do you have planned for your next trip to the berkshires?

Packing up the family and heading somewhere gorgeous for a week or weekend away can be an incredible way to escape the stress of work, school, and a busy slate of extracurriculars, but what about that adult time you and your friends have been craving? Sometimes you just need to step away and sip on something that packs a bit of a 21-and-over punch. Satisfy your craving with a visit to a few of the entries on this list of our favorite Berkshire wineries, breweries, and more!

Furnace Brook Winery at Hilltop Orchards

How do we love Furnace Brook Winery? Let us count the ways:

  1. They’re dog friendly
  2. You can sample authentic American hard ciders as well as wine
  3. It’s a great spot for apple picking
  4. It’s family owned and operated by the Vittoris
  5. You can cross country ski, hike, and go snowshoeing in between tastings
  6. Those tastings are FREE (for the first one anyway – you can taste an additional five wines for just $5)
  7. When you get hungry, there are snacks aplenty including cider donuts, fruit pies, and scones

Hilltop Orchards is open year-round from 9am-5pm daily.

Big Elm Brewing

Big Elm Brewing proprietors Bill and Christine met while working for another brewing company, eventually propelling their significant industry experience and education into their own brewery centered around “making just beer and smiles”. This love match has produced a couple kids and a ton of delicious brews, including the zesty 413 Farmhouse Ale, a creamy and oatmeal-laden Gerry Dog Stout, and the easy-drinking American Lager. The brewery also produces seasonal and specialty beers that are worthy of repeat visits just so you can stay up-to-date on the latest creations. Tours are free on Saturdays and the Tap Room is open Thursday, Friday, and Saturday so you can stop by to purchase a six-pack or a growler’s worth of your favorite brew.

Headwater Cider

Aficionados of New England-style cider crave the drink because of its crisp, fresh, dry qualities that are as refreshing as they are surprisingly sophisticated. Headwater Cider Company embraces that style wholeheartedly, using their own orchard-grown apples to press, ferment, and bottle New England cider on site. Each bottle is a blend of apples with the mix dependent on that season’s harvest; the current vintage is from 2011 and features a combination of Macintosh, Empire, and Cortland apples. Headwater Cider is widely available throughout Berkshire County and the surrounding areas. Pick up a few bottles and some sharp cheese from the local market and enjoy the scenery at the Lake House or recover from a long day of fishing with the snacky spread your group deserves.

Les Trois Emme Winery

Les Trois Emme is nestled in the wilds of the Berkshires yet visitors can still taste during the day and enjoy a show at Tanglewood or a stellar restaurant in Great Barrington at night. Better yet, bring a picnic and snag some wine from the winery and dine al fresco, soaking up the panoramic view along with a few lashings of Stingy Jack’s Pumpkin Wine or an old vine Zinfandel called Entourage. The options go on from there and you can sample them in the winery’s tasting room. A five-wine tasting is just $8 and comes with a selection of snacks to help soak up the suds, making it one of our favorite Berkshires wineries. Tours are also available when staff and operations are able to accommodate.

Bear Swamp Orchard & Cidery

This certified organic orchard is run by the Gougeon family. The Gougeons are big believers in sustainability and they’ve dedicated the last few decades to learn how to grow organic apples that taste amazing. It’s taken a ton of hard work but the result is a slew of apples – from Golden Russets to Cox Orange Pippins to Rowe Crabs – that are great for eating as well as making jams and jellies, sweet and hard ciders, vinegar, baked goods, and more. Bring the kids and pick your own bushel of apples when the fruit is in season or soak up the terroir with a few bottles of Bear Swamp Orchard Cider. A “hands off” approach means that the cider is made with minimal intervention, creating a finished product that differs little from what locals might have enjoyed centuries ago. Try the classic New England-style bottling or salute a special occasion (your lakeside Berkshire wedding perhaps?) with some sparkling organic hard cider.

Berkshire Mountain Distillers

Artisanal spirits (those made by producers other than the giant brand names normally seen on grocery store shelves) are more popular than ever and once you get a sip of the tasty treats offered up by the experts at Berkshire Mountain Distillers it’s easy to see why these smaller production liquors are getting their much-deserved time in the spotlight. Handcrafted, small-batch booze like Greylock Gin, Ragged Mountain Rum, and Ice Glen Vodka are excellent for incorporating into a mixed drink or sipping all on their own. You can now grab BMD products in 18 states but there is no substitute for an actual visit to the distillery where you can take a tour and see how the grain gets into your glass. You’ll also have a chance to taste the finished product and take some to-go from the on-property shop, too.

Balderdash Cellars

Balderdash’s tagline is “wicked wines and tall tales” and if that doesn’t entice you to visit their portfolio of fascinatingly named wines almost definitely will. From the Giraffa Chardonnay to the Truth Serum rosé to the must-try Joyride Reserve (if you’re lucky enough to come across a bottle), Balderdash Cellars is turning out delicious vino by the caseload. Stop by their tasting room, open Saturday and Sunday from 1-5pm, and enjoy some samples along with some live music to add a little ambiance to your tour of Berkshires wineries.

Carr’s Ciderhouse

Carr’s takes family-run businesses to new levels of deliciousness with their commitment to handcrafted, barrel-aged hard ciders. Apples – including variations such as Yarlington Mill, Kingston Black, Dabinett, Goldrush, and Golden Russett – are grown in the property’s orchards and then pressed in the family’s historic ciderhouse. The result is a portfolio full of hard ciders that are fruit yet elegant and equally scrumptious whether they’re consumed on their own or thoughtfully paired with a wide-ranging spread of culinary delights. The ciderhouse doesn’t have a tasting room (yet) but you can find their products at numerous local stores and farmer’s markets; stalls at the latter offer tastings as long as the market is open – perfect for a little day drinking while you pick up produce to grill back at your lakeside cottage!

Wandering Star Craft Brewery

This production brewery may not have a regular bar or a set menu but they do offer the important things – namely tours, tastings, and four hours every Saturday when you can fill up your growler with enough beer to last you another week. The brewery has 15 barrels in production at any one time, including popular options such as the Thunderbolt IPA, a seasonal pumpkin ale, a light saison, and other rotating brews. With such limited hours, Wandering Star and its staff encourage visitors to call ahead to set up any non-Saturday visits but it’s worth the hassle – these beers are tasty!

Barrington Brewery & Restaurant

The Barrington Brewery has been dishing up their own beer and a mouthwatering menu to math for more than 20 years. The menu might be classic, but the brewery itself embraces innovation as showcased by their status as the first east coast brewery to install a solar panel system to heat the facility’s water supply and generate a whopping 85% of the brewery and restaurant’s electricity. Everything on offer is made using as many local ingredients as possible and the house brews are often used to infuse items like the Cheddar Ale Soup and Chocolate Stout Cake (the latter of which was actually featured in an edition of Bon Appetit!). As for those famous solar-brewer beers, they’re made using a simple mix of water, barley, hops, yeast, and sometimes an additional scoop or two of oats or wheat. The brewmaster strives for a natural flavor by skipping any filtration or pasteurization and the beers are vegan as well as being free of additives or preservatives. Sound good? Try them for yourself. Start with something light like the Berkshire Blond and work up to the Dortmund-style Wedded Bliss before indulging in a bit of drinkable dessert with the irresistible Black Bear Stout or the fruit-laced Raspberry Ale.

Bright Ideas Brewing

The crew at Bright Ideas takes brewing super seriously. Here, surrounded by the natural beauty of Western Massachusetts, co-founders Orion Howard and Eric Kerns have built a mini-empire around the idea that beer should help foster a communal feeling and brews don’t have to be tricky. The taproom and brewery are both conveniently located in North Adams on the MASS MoCA campus. Hours change according to the seasons so call ahead or check out the website to see when you can drop by and sample beers like the ridiculously tropical 3xIPA, the chocolatey malted goodness of the Chocolate Porter, the classic British yeasty snap of the ESB, or the hoppy funk of the Saison (made with local yeast, of course).

Ready to book your weekend getaway? Gear up for a brewery tour or book into a slew of Berkshires wineries and then get yourself a comfortable home base. The boutique cottages at The Lake House offer charm, an unforgettable view, and a range of amenities ideal for groups, couples, and long lost friends looking for somewhere spectacular to organize a reunion. For more information or to make a reservation, contact our team today.