"I've always liked underdogs, which is one of the reasons I was so attracted to Pittsfield" says Megan Whilden, the city's upbeat director of cultural development since 2005. Whilden is as responsible as anyone for making Pittsfield a destination rather than just a place people drive through on their way to and from Lenox or Williamstown. She is the P.T. Barnum behind the themed 3rd Thursday street fairs (the Woodstock fair takes place on August 20 from 5 - 8 p.m.), which celebrate cultural diversity in every sense by linking together major players (Berkshire Museum, Barrington Stage Company, Colonial Theatre), galleries (Ferrin and Storefront Artist), restaurants (such as Brix, Dottie's, Pittsfield Brew Works, Pancho's), as well as less likely participants (RJ Stohr Diamonds & Fine Jewelry and St. Stephen's Episcopal Church.) When she and the Berkshire Museum's Stuart Chase and city councilman Matt Kerwood dreamed up 3rd Thursdays in the winter of 2007, she knew that focusing on art would be too limited. "I was strategic in not calling it a 3rd Thursday art walk, because I knew we had to engage local merchants and performers," she says. "One of my major goals was to change people's perception of Pittsfield. You can't overestimate the culture of negativity that was here. I wanted to change the perception and the reality. If you only change the perception, you haven't really accomplished anything." WHILDEN'S WORLD

Photograph by Nicole Garzino Where do you go when you crave serenity?I love the Canoe Meadows Wildlife Sanctuary off Holmes Road, another secret treasure of Pittsfield, the gardens at Springside Park, and Pittsfield State Forest! How great to live in a small city that has an Audubon sanctuary and a state forest within its boundaries! What are your favorite place for bargain hunting?Pittsfield has great secondhand stores. I have found wonderful things at great prices at Wild Sage, our own curiosity shop on North Street; Yours, Mine & Ours on South Street across from the Colonial Theatre, and Nora's on Tyler Street. On North Street, the Pittsfield-based Museum Facsimiles, which manufactures gorgeous frames and letterpress and silkscreened greeting cards, has a terrific outlet store next to Ferrin Gallery, and US Bluesware sells gorgeous designer clothing on consignment. What do you go when you want to splurge?I love to buy artist-designed jewelry whenever I have a chance. Almost every year I get a piece at the Pittsfield Art Show. I also love the shawls from Pine Cone Hill, which I confess I usually buy at their fantastic tent sales twice a year. And if I have an extra long day or stressful evening meetings, sometimes I'll stop by Brix Wine Bar on the way home and have a chamomile grappa. What three things do you always do with out of town guests?My two five-year-old nephews visit me from New York, and we always go to the Berkshire Museum and Hancock Shaker Village. Both are great for kids and interesting for the rest of us too! They have seen three or four different youth theatre productions while visiting as well, most recently High School Musical 2 from Barrington Stage. Who are your local heroes?My boss, Pittsfield Mayor James Ruberto, is absolutely a role model to me. His relentless optimism, contagious friendliness and genuine interest in and excitement about the arts and artists have been essential in creating positive change in Pittsfield. He is much more progressive than many people think. He encourages risk taking. Shirley Edgerton is another local hero to me. Over a decade ago she helped found the Youth Alive Step Dance & Drum Line, a local performing arts initiative that works with under-served youth in Pittsfield. She's also the cofounder of the Berkshire County Women of Color Giving Circle, a grassroots philanthropic group, and co-creator of a musical entitled Aint I A Woman: Unsung African-American Civil Rights Heroines, which has been performed twice in Pittsfield with an intergenerational local cast. The Mayor and I had walk on parts in the second performance (below photo.)

Third Thursdays succeed because they bring together the city's Old Guard and Young Turks. By connecting the dots on Third Thursdays and with the weekly Cultural Pittsfield email newsletter, Whilden has managed to create a portrait of a scrappy city that embraces and encourages artistic enterprises of every sort. "We're the Brooklyn of the Berkshires," she says. "We're funky, diverse, and neighborhoody."

Pittsfield is not Whilden's city of origin, but it is her city of choice, which is surprising considering her background. A fifth-generation Californian, she grew up in Monterey, CA, where her great grandfather was the mayor. Whilden moved to San Francisco for college (and the punk rock scene) in 1980, and eventually went to work at the corporate offices of Williams-Sonoma in the product information department. She left to work for a not-for-profit psychological association, and then moved in 1992 to Washington, DC, where she went to work for the AIDS Action Council. "We were the political arm of the AIDS movement," she says, explaining that she had to manage a coalition of 160 national AIDS organization to advocate on policy on issues such as needle exchange and mandatory HIV testing of newborns. "That's where I learned about collaboration and communication. I would send out weekly faxes to keep everybody informed on what we were doing. It's what I do with the Cultural Pittsfield newsletter." After three long years in Washington she was ready to leave. "I always think of that time in dog years—one year was like seven," she says. "AIDS is intense and politics is intense. I thought Washington was such a segregated and unhappy city. You wake up and go to sleep listening to CNN or NPR. It's a workaholic town." Her next stop was New York, where she was hired as the associate publisher of Parabola magazine, which is produced by the Society for the Study of Myth and Tradition. And when her then boyfriend got a job in the Berkshires, she decided to follow him, and they rented a house in Sandisfield. When she and the boyfriend broke up, Whilden, who was working as the marketing director for IS 183 Art School of the Berkshires, moved to Pittsfield, where she became friends with painter Maggie Mailer. "She had started the Storefront Artist Project, and I got immersed in what she was doing," says Whilden, recalling various artists who once worked in vacant spaces on North Street, which are now occupied by businesses such as Jae's Spice.

Whilden (trying on a 3rd Thursday Woodstock costume left) was frustrated that while she saw the glass half full in Pittsfield most people saw it as half empty. She started a chatty, gossipy "City Scene" column for the Berkshire Eagle, which chronicled the goings on in town. She was inspired by a group that was hoping to get women and minorities elected to the all-white, all-male city council. "Officially, WHEN stood for Women Help Empower Neighborhoods but it was also We've Had Enough Nonsense." In the fall of 2003, seven out of eleven city council members were voted out of office and Jim Ruberto, who had grown up in Pittsfield but had not lived there for 30 years, was elected mayor. The mayor searched for a year for someone to head up a new office of cultural development, and he pushed Whilden through the city council. Whilden and Ruberto have a mutual admiration society. "I often attribute my positivity and enthusiasm to the mayor, " she says. Whilden is a beloved and admired leader. "Megan has been able to change the public's perception about the city," says Ellen Spear, the president of Pittsfield's Hancock Shaker Village. "It is now considered a place to come to see, experience and make art. That's no small accomplishment. And the spirit of collaboration—already a Berkshire ethic—has become even more pervasive in Pittsfield. Megan is a great communicator, keeping people in touch and informed about one another's work." Joyce Bernstein, who is the co-owner/developer of three buildings on North Street and member of MASS MoCA's board, says: "Although she doesn’t love me for it, I like to introduce Megan as Pittsfield’s Cultural Czarina. I think that Megan has given new meaning to the terms 'community activist' and 'special interest group.' She has brought together diverse groups of people, of all ages, discovered and nurtured what makes them special and then provided venues and created events that showcase their talents and the community’s breadth." Whilden is indefatigable in her support of Pittsfield businesses and organizations, and she knows that reviving the city depends on many factors. "I spent a year encouraging the owner of The Lantern to fix his terrific neon sign," she says while drinking a glass of wine at Mission Bar + Tapas's sidewalk cafe, which is across from the glowing Lantern sign. "The bottom line about Pittsfield is that an individual can make a difference, and that's pretty amazing." And so is Megan Whilden.