Head for the Hills: Things to Do in the Berkshires

Just a hop, skip, and jump away from Boston and New York lies a collection of towns offering the perfect excuse to pack your bags and go for a road trip. As you drive through the beautiful hills of western Massachusetts, be sure to experience the full range of things to do in the Berkshires: unique restaurants, eclectic museums, historic landmarks , and renowned inns and resorts.

Can't-Miss Things to Do in the Berkshires

While the Berkshires are amazing all year round, the summertime makes the Berkshires a mecca of outdoor adventuring and exploring local culture. For the thrill enthusiast check out Zoar Outdoor in Charlemont, MA, which leads daily white water rafting, ziplining, and kayaking trips for all ages. To explore the landscape, The Cascade Trail in North Adams leads you along the Notch Brook to a 40-foot cascading waterfall. For that always-possible rainy day (it is New England, after all), the Lee Premium Outlets in Lee, Mass., is home to over 25 name brand stores, where you can be sure you'll find a great deal.

Museums in the Berkshires

A couple of New England's most celebrated art museums are hidden amongst the rolling hills of the Berkshires. The Clark in Williamstown, MA, is home to a massive collection and is known especially for French Impressionist works.15 minutes to the east in North Adams, Mass MoCA shows off the best in contemporary art on a campus made up of repurposed factory buildings. During the summer you can hear the sweet sounds of  Wilco’s own Annual Solid Sound Festival or go full folk at the Fresh Grass Festival, two of the biggest live music events on the museum's grounds.

Where to Eat and Drink

The Berkshires do not disappoint when it comes to fine dining and one of a kind cuisine. Many restaurants have received national press and have captured the heart of the Berkshires with each chef's unique taste. Haven Cafe and Bakery in Lenox, MA  has you covered for breakfast with their famous benedicts and hearty pancakes you are sure to not leave hungry. When you're on the road, How We Roll, a local Berkshires food truck serves up unexpected combinations served in egg roll wrappers such as mango and pulled pork. After gallivanting around town you're sure to work up an appetite for an afternoon treat. Ayeladas in Pittsfield, MA, offers four unique daily flavors (from a vault of 400) of frozen yogurt made fresh from local milk.  Alta Restaurant and Wine Bar located in Lenox, MA, uses organic and local ingredients to create mouthwatering plates that pair beautifully with their extensive wine list .Combining the unique setting of a historic 1700s grist mill turned inn and restaurant with Chef Ivy’s contemporary approach to decadent french cuisine, The Mill on the Floss in New Ashford, MA, is an excellent choice for dinner.

Where to Stay in the Berkshires

A trip to the Berkshires isn't complete without a stay at one of the beautiful and historic inns and resorts the area offers. In Lenox, MA the award-winning Cranwell Spa & Golf Resort features a historic 18-hole golf course and one of the largest resort spas in the Northeast. Also in Lenox is one of the premier health resorts Canyon Ranch, perfect for the wellness minded individual or a couple looking for a relaxing getaway. Choose from one of forty daily fitness classes, gourmet dishes, luxurious spa treatments, and professional health resources to tailor your stay to your exact needs. The 1896 House in Williamstown, MA is perfect for any traveler offering two lovely inns, a romantic Bed and Breakfast, and luxurious suites. The hotel grounds are inspired by natural beauty and are close enough to all of the restaurants and attractions to make this the perfect getaway.  Click here to see our full list of exceptional places to stay in the Berkshires. 

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