Fifteen years ago, my daughter and new son-in-law moved to Pittsfield, MA. It’s given me an opportunity to learn and love the Berkshires.
A quick note on weekly classes before we get into it
Claim your spot in Painting Nocturnes, Tuesday evenings or Painting Water, Monday evenings. Both are 6-9 PM, starting the week of August 17, 2026.
I upload videos of these online classes and you have access to them forever (or for as long as there’s YouTube.) That means you can review them if you feel you need a refresher or have to cut out early for some reason.
Artists and writers, poets and performers
Among the great artists who’ve worked in the Berkshire were Thomas Cole, George Inness, Norman Rockwell (who lived there for the last 25 years of his life) and sculptor Daniel Chester French.
Writers included Herman Melville (who wrote much of Moby-Dick there), Edith Wharton, Nathaniel Hawthorne, Henry David Thoreau and William Cullen Bryant.
Musicians and performing artists have been drawn to Tanglewood, including Leonard Bernstein, Aaron Copeland, Yo-Yo Ma, James Taylor and Ted Shawn, whose Jacob’s Pillow in Becket is America’s oldest dance festival.
It’s close to both New York and Boston
One reason artists love the Berkshires is its proximity to the two centers of 19th century culture. Today you can get there from New York City in less than three hours by car and from Boston in two hours.
It’s beautiful
There are endless back roads, small mountain lakes and rolling green mountains. One can paint broad mountain vistas, a New England village green and a tumbling stream, all within a few miles of one another. The Berkshires are full of sweet surprises. Every bend in the road reveals another weathered barn, old stone wall, maple grove or hillside pasture.
The light is very different from coastal Maine or Arizona, but every bit as lovely. There can be luminous mornings, towering cumulus clouds in the afternoon and long, glowing evenings. The hills overlap in increasingly cool blues, giving wonderful opportunities to practice atmospheric perspective without it feeling contrived.
Shaker country
The American Shaker community was founded in nearby Watervliet, NY, but the whole of western Massachusetts is Shaker country. The most extensive renovated site is the Shaker village in Hancock, MA. I’ve brought groups there for several years and I always find things I’d never noticed before. Beyond the Shakers, there are white spires of churches, bustling old downtowns, apple orchards and horse farms. If you can’t find something that enraptures you, you’re not trying.
If the Berkshires have been calling your name, why not answer? Find Your Authentic Voice in Plein Air is a five-day workshop designed to help you move beyond simply recording what you see and toward painting with confidence, clarity, and your own authentic voice. It includes plenty of individual instruction, demonstrations and thoughtful critiques that will strengthen both your technical skills and your artistic vision. Painters in oils, watercolor, acrylic, gouache, and pastel at any level are welcome.
The workshop runs from August 10–14, 2026 and enrollment is limited so everyone receives plenty of personal attention. Whether you’re looking to sharpen your plein air skills, reconnect with the joy of painting outdoors, or just learn to paint, I’d love to have you join us.
Registration is now open for workshops in 2026! Reserve your spot:
- Sea & Sky | Acadia National Park, ME, August 2–7, 2026
- Find your Authentic Voice in Plein Air | Berkshires, MA, August 10-14, 2026
- New! Color Clinic 2026 | Rockport, ME, October 3-4, 2026
- New! Composition Week 2026 | Rockport, ME, October 5-9, 2026
Can’t commit to a full workshop? Work online at your own pace:
I cannot wait to get there in August! I love the diverse subject matter the area has.
I hope we have a nice full group of fellow painters! Come one come all!