The Most Instagram-Worthy Spots in the Berkshires

Do it for the gram: A saying used by millennials to describe things that are done solely for the purpose of taking pictures to enhance your social feeds. We think you shouldn’t have to spend your hard earned money on extravagant things to have an appealing Instagram. So, we’ve created a list of some pretty awesome destinations throughout the Berkshires that you won’t want to miss out on experiencing. The great photos you will capture are just an added bonus. After-all, pic or it didn’t happen, am I right?


Where: 5 Prospect Hill Rd, Stockbridge, MA 01262
Why: This former country estate of a noted New York City lawyer is known for it’s a stunning gilded age mansion but it is its sprawling gardens and pine tree lined driveway that create the ideal Berkshires Instagram moment.

Sources: @naumkeagofficial @joannvieira

The Southfield Store

Where: 163 Norfolk Rd, Southfield, MA 01259
Why: Colorful displays, latte art and scrumptious bites garnished with delicate flowers are sure to brighten up your feed.

Source: @thesouthfieldstore

Chesterwood Museum

Where: 3 Williamsville Rd, Stockbridge, MA 01262
Why: The former summer estate of sculptor Daniel Chester French is home to the prototype for the renowned national monument. Come here to see – and snap photos of the “original” Lincoln memorial. While you’re at it, wander around the 150-acre property filled with gardens, fountains and unbeatable relics.

Sources: @kvogelnest & @jasonbakerphotography

Pleasant and Main

Where: 063 Main St, Housatonic, MA 01236
Why: This homey cafe filled with knickknacks and flowers lends way for an awesome foodie post with a whimsical feel.

Sources: @pleasantandmain & @Shivashanti333

The Dream Away Lodge

Where: 342 County Rd, Becket, MA 01223
Why: This quirky restaurant boasts “an atmosphere long remembered” made famous by guests such as Arlo Guthrie and Bob Dylan. Stop for a bite, drink, live music and #vibes that will give your Instagram grid some vintage charm.

Sources: @mikamintz@thedreamawaylodge & @makeuphairbylyz


Where: 75 Main Rd, Lee, MA 01238
Why: Known by locals as Tyringham’s Gingerbread House this unique property will make you feel as though you’ve stepped into a childrens’ storybook. Stained glass windows, gardens and a lily pond create an enchanting photo-op you won’t want to miss.

Sources: @k8winslow

The Bistro Box

Where: 937 S Main St, Great Barrington, MA 01230
Why: Who doesn’t love making their insta-followers jealous with a delicious-looking snap of a great meal? The Bistro Box has you covered. This roadside burger joint has everything you need for the ideal foodie post. Colorful drinks, glass-bottled sodas, juicy burgers. Even your furry friends will love this spot!

Sources: @jodettefelder & @thebistrobox

Bash Bish Falls

Where: Mount Washington, Massachusetts
Why: Obligatory waterfall selfie anyone?! It’s obvious why Bash Bish Falls makes our list. These stunning falls are not only the highest in the state, but they located right here, in the Berkshires. This view will give you #AlltheFeels.

Sources: @chenkathyy, @corileeee & skibbleyd83

Tyler and Pine Bakery

Where: 339 Tyler St, Pittsfield, MA 01201
Why: It’s easy to see why donuts have become an insta-craze in recent years – sugary deliciousness that is also pretty to look at? Win, Win. Tyler and Pine takes donuts to the next level with unique flavors and toppings. They’ll even whip up some pretty sweet custom cakes – pun intended!

Sources: @forkitover @tylerandpinebakery

Olivia’s Overlook

Where: Michael H. Walsh Trail, West Stockbridge, MA 01266
Why: This scenic overlook is not only the best picnic spot in the county, but it’s also a great place for a photo with the Berkshire mountains and Stockbridge Bowl as your backdrop. You will feel and look like you’re on top of the world.

Sources: @foxbos10@jennrose_wilson & @agentstiless


Where: 1040 Mass MoCA Way, North Adams, MA 01247
Why: It’s no secret that the largest contemporary art museum has stunning exhibits – exhibits that are now becoming some pretty great instagramable moments. Exposed light bulbs and bight colored works of art create fun backdrops that will show off your cultural side.

Sources: @emiilybullard@massmoca & @Jeffleblancmusic by Leah Harkin

These local insta-destinations are sure to amp-up your social presence. Just make sure that once you get that perfect shot,  you don’t forget to look up from your screen and enjoy the amazing moments these places will offer!