PITTSFIELD — The last few weeks have reminded Megan Whilden that symptoms of anxiety and excitement are often indistinguishable from one another. “Your body’s on alert and wants to make sure you get everything done,” said Whilden who, as of today, is simultaneously stepping down as the executive director of the Osher Lifelong Learning Institute at Berkshire Community College (OLLI) and returning to her native California. Over the past two decades, Whilden has become synonymous with culture, community, and change — all of which she’s both fostered and facilitated in multiple roles across the nonprofit sector.
Whilden was appointed Pittsfield’s inaugural cultural development director in 2005, and her local involvement has spanned the county’s NAACP chapter and the co-founding the Four Freedoms Coalition after the 2016 election. She has also served on the boards of 1Berkshire and Women Helping Empower Neighborhoods. In 2014, Whilden joined the ranks at OLLI.

For years, Whilden was met with the same comment from locals: “People from California only stay in the Berkshires three years and then they leave!” Suffice it to say, she broke the mold and proved many wrong — all to Berkshire County’s collective benefit. Below is an excerpted version of our conversation earlier this month.
Hannah Van Sickle: Looking back, what attracted you to the Berkshires in the first place?
Megan Whilden: I lived in New York City for a couple of years (which everyone should do at some point, or not!), we had friends in the Berkshires, my partner at the time got a job here, and I was ready for a new adventure — so we moved. We lived in Sandisfield, way out in the country, and were invited by some neighbors down the road to a New Year’s Eve party, which was very nice. We were kind of dirty and sweaty from moving but we felt like we’re in this little tiny country town in the boonies and it’s winter, so we went — and everyone was in black tie (it was Liana Toscanini’s house!) It wasn’t a formal party, they were just having fun dressing up, so we felt very comfortable after our shock. That was a great introduction to the Berkshires, [one] that foretells how friendly and welcoming the [area] is. After a couple of years we broke up, and my partner actually left, but I stayed.
HVS: Considering your career, spanning various organizations and two decades, is there a common thread binding your work together?

MW: In some ways, I guess I’ve been a storyteller for the Berkshires, [tasked with] reminding people where they’ve come from and where they’re going. Sometimes it has to be someone from the outside who comes and shines up a mirror that has gotten dusty and turns it to show people: Look, this is a beautiful town in a beautiful setting, and there are lots of interesting people here [who are] passionate about community, the arts, and helping each other. So, I felt like one of my main jobs [has been to show the] possibility that exists here, and that we can work together to make things even better. Beginning with the Storefront Artists Project and continuing to the present and OLLI, the through line [is] about community and creativity, curiosity and caring — and communication. It’s the live wire that goes between people. If people are communicating with each other, that’s what creates community; it can spark creativity and inspire caring. Connecting people is a joy.
HVS: You’ve chosen to wear many hats over the years; what has kept you rooted here?
MW: I love the Berkshires, and I love that it’s human-scaled; it’s not not too big, and it’s also not too small. You can make a difference; people are open to working together. When [colleagues and I] used to go to meetings in Boston or with statewide groups, people would often tell us the Berkshires are a model of collaboration not often seen elsewhere, and it’s fun. Because Pittsfield had challenges after GE left, people were open to trying new things. [Former] Mayor James Roberto had lived in a lot of cities around the country … and he knew that arts and culture were essential to any thriving city — and letting people do what they do also encourages creativity. This translates to OLLI: people don’t realize that all of our amazing programs are created, taught, and organized by OLLI volunteers; I am not responsible for them. Allowing that kind of creativity to come through people is a win-win. It’s delightful.
HVS: Is there a single accomplishment, or overarching goal you met, that stands out among your many contributions to the community?

MW: I think everything is a process, and I don’t work in a goal-oriented way. That’s just me. Are goals ever reached?
HVS: As you move on from the 413, what are the lessons you’ve learned here that will shape your next chapter?
MW: OLLI has taught me about the incredible resourcefulness, knowledge, and passion among older adults in this community. You know, it’s such a treasure, and these are people who have lived a lifetime of varied experiences and knowledge and they want to give back to the community. Many of them are newer to the Berkshires, and bring with them experience from other places and want to participate. Often the culture will grab them first, not unlike a bear grabbing the salmon as they go upstream, but they’re also interested in other things about the Berkshires.
Working with OLLI has also made me realize how prevalent and unchallenged ageism is; [it’s] one of the last acceptable prejudices. The fact that you can buy a birthday card in Walgreens that makes fun of old people, completely unchallenged, continues to be eye opening. The world as a whole is getting older, the Berkshires and Massachusetts are, and getting older is changing. If you associate growing older with diminished abilities, mentally and physically, your mental and physical abilities will diminish. People who have a negative idea of growing older actually get sicker and die quicker. So it actually is a dangerous, dangerous belief in that way.
Unconsciously, we have a very narrow idea of what growing older looks like; for older people. It’s really important to expand the idea of what it’s like — you could lead a drum circle like Otha Day, you could be a ceramicist like June Wink. OLLI has expanded [the community’s] view, and I hope I contributed a little to that, too.