WINERIES AND BREWERIES

wineries and breweries in pittsfield, MA

Visiting a local brewery or winery and tasting a local libation paired with a savory meal can be a great way to spend the day. Lucky for you, the Berkshires have many fantastic creators of adult beverages, enough that it’s a difficult decision to determine which ones to stop by during your visit. 


We’ve put together a list below of some nearby locations. Keep in mind that this is by no means a comprehensive list of wineries and breweries near Pittsfield, MA, just some recommendations to get you started.

Balderdash Cellars

  • Address: 81 State Rd, Richmond, MA
  • Hours: Changes with the season
  • Distance from Us: ~9 miles


Balderdash Cellars was founded in 2011, fighting against the odds to become one of the most notable wineries in the Berkshires today.  Working closely with two vineyards from California, the owners and staff toil continuously to craft immaculate white, rose, and red wines.


While reservations to visit the winery are not required, Balderdash Cellars does require groups of 25 and over to have a dedicated bartender. They have a ‘bring your own food’ policy, which works well seeing as they work with local food trucks to come by and offer great local food. In addition, this winery near Pittsfield, MA has live music onsite regularly, showcasing musicians from around the region.


Please note that there is a strict no smoking/vaping policy here, and bringing in outside alcoholic beverages is expressly forbidden.

Hilltop Orchards

  • Address: 508 Canaan Rd, Richmond, MA
  • Hours: Daily 9AM - 5PM
  • Distance from us: ~12.5 miles


With over 100 years of cider and wine making to their name, Hilltop Orchards is a family-run cidery and winery that is one of the biggest staples in the whole region. Everything involved in the cider making process is done here, from the picking of fresh apples to the making of small batch products.


The orchards can easily provide an entire days worth of activities, such as:

  • Cider and Wine Tastings
  • Extensive Cidery Tours
  • Hiking/Snowshoeing across a 200-acre orchard
  • Enjoy a comfortable stay by a fireplace on a cold day


Hilltop Orchards doesn’t only make libations, they also are famous for their freshly made apple cider donuts as well as a variety of other small batch products, such as hot sauce and apple butter.

Wandering Star Craft Brewery

  • Address: 11 Gifford St, Pittsfield, MA
  • Hours: Fri: 4-8PM, Sat-Sun: 12-5 PM, Closed Mon - Thurs
  • Distance from Us: ~5 miles


The Wandering Star Craft Brewery gives off a homey feel, as if you were stopping by your neighbor’s garage to share a drink. However, while this brewery may be small, it certainly has made a big impact in the community.


Once you walk in, after being greeted by one of the friendly cats that live there, you can expect a small selection of excellent brews for reasonable prices. There is plenty of outdoor space to sit at the Wandering Star brewery and the owner/brewer/bartender is friendly and accommodating. 

Barrington Brewery & Restaurant

  • Address: 420 Stockbridge Rd Unit 4, Great Barrington, MA
  • Hours: Mon,Weds,Thurs: 11:30AM-9PM, Fri-Sun: 11:30AM-9:30PM, Sun: 11:30AM-8:30PM, Closed Tues
  • Distance from us: ~22 miles


Established in 1995, Barrington Brewery & Restaurant is a shining example of not only how to make a local brewery last throughout the years sustainably. This brewery became the first on the east coast to incorporate solar power to create their signature brews using a seven-barrel system.


Part of what sets Barrington Brewery apart is the food that they serve alongside their libations. The establishment serves a full size menu consisting of pub fare and american classics as well as offering daily specials, all of which are locally sourced when possible. 


Their crafted beverage list mainly consists of ale, although it does expand greatly during the warmer months.

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