Folk music icon Arlo Guthrie performs a free outdoor concert earlier this month in New York City.

AP / Jason DeCrow Jason DeCrow

WASHINGTON, Mass. This year has already marked several milestone anniversaries in the life of Arlo Guthrie, unrepentant litterbug and patriarch of one of America’s iconic musical families.

On July 10, the silver-haired singer-songwriter celebrated his 60th birthday here at his hillside compound in the Berkshires, surrounded by his four children and a brood of grandchildren. The party, a low-key burgers-and-beer affair, came in the middle of a rare solo tour by Guthrie and coincided with the release of a new live recording titled In Times Like These, on which Guthrie is accompanied by the University of Kentucky Symphony Orchestra.

Two noteworthy 40th anniversaries have also rolled around, or soon will. One is pegged to the release of Alice’s Restaurant, the 18-minute song and album of the same name that put Guthrie on the pop-music map during the hippie-fied Summer of Love. Last month, Rolling Stone magazine named Guthrie’s album one of 1967’s rock masterpieces, up there with the Beatles’ Sgt. Pepper’s Lonely Hearts Club Band.

The other, more solemn anniversary commemorates the death of Guthrie’s father, folk-music legend Woody Guthrie, who succumbed to Huntington’s disease on Oct. 3, 1967, at age 55.

Somewhere in between the concert gigs and birthday candles, Tom Brokaw scheduled an interview with Guthrie for his next book, and celebrity photographer Annie Leibovitz showed up at Camp Guthrie to snap a family portrait for Vanity Fair.

“She was a real pro, as nice as she could be,” says Guthrie, still slightly dazed from the glossy home invasion. “But man, it took all day.”

Given all that’s happened in recent weeks — Vanity Fair? Sixtieth birthday? — one might expect to find Guthrie in a nostalgic frame of mind (he even looks like he just stumbled out of the Woodstock festival parking lot).

Or not.

Reflective, maybe. Contented, absolutely. Nostalgic? Not his style, sorry.

HE’LL HAPPILY TALK about the life of the working folk singer and the benefits of yoga, which he practices religiously and even teaches on occasion. About why taking musical risks is so important at this stage of his career and why the “Ricky Nelson syndrome” of recycling old audience-pleasing hits is such a drag.

“If you do anything for 40 years, you can do it comfortably,” says Guthrie, sitting by his backyard swimming pool one morning late last month while his wife, Jackie, sets down glasses of iced tea. “And it will always be good. But unless you’re willing to risk it being bad, it can never be great.”

He’ll ramble on, too, replete with Arlo-esque flourishes, about why he may never tackle another acting job or write another kids’ book, both of which he’s done. Or, conversely, why he just might, provided the right offer comes rumbling down life’s highway and makes a left turn up his winding, unpaved road.

“After I finished the first book,” Guthrie says with a grin, “my publisher asked what the next one was about. What next one? I said. This ain’t Harry Potter.”

To make the light in Guthrie’s eyes really shine, bring up the Guthrie Center, in nearby Great Barrington, which sponsors a variety of community-building projects, ranging from puppet shows to yoga classes. “It’s all the positive remnants of the ’60s,” he says with apparent satisfaction. “Everything that’s gotten lost over the past 10 to 15 years.”

Or mention Pete Seeger, Guthrie’s lifelong friend and mentor, whose legacy was recently recaptured for younger audiences by Bruce Springsteen, another living legend.

“Pete and my dad both realized the history of people in song was being lost,” Guthrie says with genuine emotion. “When I look at what I’m doing here, I agree with them philosophically. It’s why I do songs like ‘St. James Infirmary’ and ‘Goodnight Irene’ [on the new album]. I’m not just a singer-songwriter doing songs in the key of me.”

AS FAR AS “ALICE,” goes, though, Guthrie doesn’t live there anymore. Disregarding some public-nuisance issues down in Florida, which we’ll get to in a moment.

“To be honest, I had no idea it was the anniversary of the Summer of Love until someone e-mailed me about Rolling Stone,” Guthrie says with a shrug. “We don’t really track that stuff, you know.”

He smiles and lights a cigarette. “I left the entertainment-industry part of my life behind in 1983, when we decided not to work with major record companies anymore,” says Guthrie, who launched his own label, Rising Son Records, that year and whose music business now includes all four children. “It made life so much easier. No one looking over your shoulder or deciding what songs should be on your record. That was a long time ago.

“I had a great run, no question. Woodstock. The Alice’s Restaurant movie. ‘City of New Orleans.’ I recommend it to anyone who’s 18. But as a life? No thanks.”

If any mile marker has proved meaningful, Guthrie continues, it was the day he outlived his father. Huntington’s disease, a genetically inherited neurological disorder for which there is no cure, struck Woody Guthrie in his late 40s. Arlo Guthrie made the decision years ago not to be tested. He’s at peace with that, too.

“I spent the day talking to my dad about it, as it were,” he says, visions of another classic Arlo monologue about fame, family, and fate dancing in the air. “I said, ‘All right, there’s progress. And if my kids live a day older than I get to be, we’re moving in the right direction, anyway.’ ”

Clearly they’re moving forward musically. Abe Guthrie is a guitarist, keyboard player and vocalist who’s toured with his dad for 20 years when not fronting his own band, Xavier. Sarah Lee Guthrie records and performs with her husband, alt-folkie Johnny Irion. Cathy Guthrie comprises one half of the duo Folk Uke. Her performing partner is Amy Nelson, daughter of Willie; the duo’s name plays not only on their chirpy, ukulele-based sound but on their R-rated lyrics as well. When their two famous fathers join them onstage, Arlo and Willie are introduced as the Horse You Rode in On.

“Cathy was going to be the smart one and go to college,” Guthrie says with a laugh. “After a year, she tells me she’s learning the ukulele. ‘It’s not serious,’ she says. ‘It’s only four strings.’ ‘Yeah,’ I say, ‘it starts with four strings. But pretty soon you’re up to five strings, then six.’ ”

Annie Guthrie runs the family business office. Along with her three siblings, she’s moved back to the Berkshires compound her parents bought in 1969.

The farmstead has expanded over the decades to include several dwellings, a business office and home recording studio, and 400 secluded acres. Scattered about are vestiges of Guthrie’s troubadour past, including a 1954 tour bus that Guthrie piloted himself when his kids were in diapers.

Now, about that situation in Florida. Twenty years ago, Guthrie bought an old Coast Guard building in Roseland, intending to make it his winter base of operations. In 2005, he built an addition for his record company and mail-order business. Then, two hurricanes came along and tore the addition apart. Guthrie had no insurance — he could milk that for another 18-minute monologue — and was stuck with roughly $1 million in damages and no blueprint on how to rebuild, even if he wished to.

To make a long story short, which is seldom Guthrie’s style, he was cited by the local code enforcement board this year for maintaining an unsafe building and creating a public nuisance. Suffice to say, news accounts of his head-butting with local authorities drew parallels to “Alice’s Restaurant,” his famous song about being busted for littering one Thanksgiving Day in the mid-’60s.

THREE WEEKS AGO, Guthrie attended a board hearing in Florida and was granted a 90-day extension to resolve the problem. “We were going to sell the place,” he says, “but now we’ll see if we can’t pull it out. Luckily, because of the news coverage, a lot of people have offered to help us.”

He waves at a couple of young grandkids passing by. Unlike some investments, he says, the Florida property can be used and enjoyed for generations, long after he’s gone.

“It’s not like putting money into some hedge fund,” he points out. “I mean, we’re folk singers. We don’t understand that other stuff.”