Woodstock, New York, US: Staying at Big Pink is like hanging out with Bob Dylan and The Band

The door to the basement wasn't supposed to be unlocked. The booking website strictly states that when staying at the fabled Big Pink, just near Woodstock in upstate New York, one can partake in a guided tour down there with a local expert but it's not open to explore alone. We've rented the rest of house for the weekend. This is where, 50 years ago, Bob Dylan, the Nobel laureate in literature, tinkered on an Olivetti typewriter, producing 139 songs with The Band, including I Shall Be Released and This Wheel's on Fire, and then headed downstairs to rehearse and record them.

It might have been the charm of my New York-based friends who booked the two-storey house or that the cleaner accidentally left the basement door unlocked, but who could resist taking a sneaky peek where both The Basement Tapes and The Band's Music from Big Pink began. Back in the '60s Dylan would drive his baby blue Mustang daily from his nearby home to the pink house where four members of The Band lived. They'd gather to write and play, using a reel-to-reel tape recorder.

Tiptoeing downstairs we see it's set up as it would have been back then. Among the cinder block walls is an upright piano, drums, bass, guitar with amps and mic. All that's missing is the dog, Hamlet, who used to sprawl out on the Persian rug and watch.

Big Pink hasn't changed much over the years. Look at the photo on the back of The Band's debut record and, except for a few extra shrubs, the "pink house seated in the sun of Overlook Mountain in West Saugerties, New York" (as the album cover describes it) looks identical. Depending on traffic, it takes about two hours to get here from Manhattan. Skyscrapers make way for the winding tree-lined dirt roads of the Catskills region, an area covering 15,540 square kilometres made up of mountains, rivers, forests and parkland.

The Catskills is home to towns such as Phoenicia, Saugerties and the most famous of the lot, Woodstock. It has long been a haven for musicians and creative types, longing for respite from the city. Away from the high-rises and city heat are open starry skies, fresh air, space. Bob Dylan once said that Woodstock was a place where "we stop the clouds, turn time back and inside out, make the sun turn on and of". He called it, "the greatest, man, the greatest place".

It's here in the Catskills that the Woodstock Music and Art Fair took place 50 years ago, though it was a misnomer all along. The three-day music festival was held on Max Yasgur's dairy farm which was not in Woodstock but an-hour-and-a-half's drive away near Bethel. They called it Woodstock because the area had a reputation; Dylan lived here. Later, Janis Joplin and Jimi Hendrix followed. Van Morrison wrote Moondance here.

Half-a-million music fans descended on the farm, 350,000 more than expected. It was muddy; food was scarce; sanitation levels were low but the event remained a peaceful celebration. Woodstock became one of the defining events of the era. The Who belted out My Generation, Joe Cocker got by with a little help from his friends and Jimi Hendrix closed out the festival playing at 9am on a Monday morning.

One of the original festival organisers, Michael Lang, has recently announced a three-day festival will be held at Watkins Glen to commemorate the 50th anniversary in August. Concert-goers can expect glamping and portaloos instead of the muddy chaos of the event held half a century ago. And at the original site in Bethel Woods, where there's now a 15,000-seat pavilion, there will be another tribute. The anniversary is one of the reasons why the Catskills was named as one of the top 10 regions of the world in Lonely Planet's Best in Travel 2019.

On the main drag in the town of Woodstock you can still buy tie-dye T-shirts and incense. There are people strumming guitars on the Village Green. Musicians still set up studios up here, among the mountains and fresh air. The area is renowned for its natural beauty. There's a "no glass" rule at the local swimming hole so people drink beer from cans while bald eagles fly overhead. Others take hikes to Kaaterskill Falls to see the waterfalls.

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Back at Big Pink we're setting up the barbecue using the logs neatly piled alongside it. A hire car pulls up with fans from Stockholm wanting to take a photo of the famous house. In Big Pink's thick guestbook there are tributes to the musicians, including sketches of Dylan, and lyrics.

Looking up at the night sky, you can imagine Dylan sitting there doing the same, or maybe The Band's drummer, Levon Helm, playing behind the beat, shoulders shrugged, or guitarist Robbie Robertson pontificating in the kitchen. There's a certain allure to being in the same place in which some of your musical heroes wrote and recorded; to try to glean some kind of essence, and to make guesses about what might have happened in this exact spot.

This is why Graceland is still popular 42 years after the King's death and why Abbey Road studios in London is high on the Beatles pilgrimage trail. Bob Dylan himself is not immune to such adventures. When he visited Sun Records in Memphis, ol' Bob reportedly kissed the floor where Elvis first recorded. And in Hamburg, my Beatles tour guide told me she once saw Bob standing there, checking out the spot where the Star-Club once stood.

Throughout Big Pink there are reminders; a framed photo of The Band, a copy of Dylan's book, Chronicles, the soundtrack to The Last Waltz, Martin Scorsese's swansong paean to The Band. There's no doubt Big Pink was a place they all loved. Levon Helm once said The Band had a pact that should one member die on the road, the others would put the body on ice and haul him back to Woodstock before the police could get involved.

Just two of the five members of The Band are still alive and, on that late summer night, there may or may not have been spirits among us. How did that full bottle of vodka fall off the top of the fridge and smash to the ground when no one was nearby? What about those footsteps my friend heard behind her as she walked through the backyard alone? And most alarmingly, the Charlie Rich song (Life Has Its Little Ups and Downs) that came on the stereo twice in a row at 6am when everyone was asleep. Turns out Rich is one of Dylan's favourites.

The next night, my friends, accomplished musicians all, walked across the scuffed floors to descend the staircase to the Big Pink's basement. Come 2am, after about 20 rehearsals of The Night They Drove Old Dixie Down, we nailed it. Though never matching the subtly spectacular drawl of Levon Helm, nor the vocal harmonies, the half beat of the drums was spot-on, and that piano beautifully echoed beyond the pines across to Overlook Mountain. We then turned off the amps, carefully placed the instruments back exactly where they had been and closed the door to the basement.

WHERE TO GO IN THE CATSKILLS

THE MUSEUM AT BETHEL WOODS

The exhibitions at this museum capture some of the essence of the 1969 Woodstock festival. We Are Golden, one of its most recent exhibitions; it looks into Woodstock and what the youth of 1969 wanted for the world. See bethelwoodscenter.org

PHOENICIA DINER, PHOENICIA

Don't be fooled into thinking this is a run-of-the-mill roadside restaurant. The 1960s diner has been immaculately refurbished and produce is sourced locally – try the smoked trout, and if you're game, the bourbon milkshake. Open for breakfast and lunch. See phoeniciadiner.com.

LEVON'S MIDNIGHT RAMBLE, WOODSTOCK

The Band's Levon Helm may have passed away but the Midnight Rambles at his property live on. His daughter, Amy, also a musician, regularly invites renowned performers to play in The Barn. See levonhelm.com

SUNFROST FARMS, WOODSTOCK

Stop off for delicious fresh produce at Sunfrost Farms. It also does great takeaway vegie burgers, and there's a flower nursery you can browse while you're there. See sunfrostfarms.com

LOVEFIELD VINTAGE, KINGSTON

The town of Kingston In the nearby Hudson Valley is worth a visit. Stop into this vintage boutique for one-offs including affordable Ossie Clark pieces, and a good selection of boots and accessories. See lovefieldvintage.com

TRIP NOTES

MORE

traveller.com.au/north-america

visitthecatskills.com/

VISIT

The 50th anniversary of the Woodstock concert will take place in August 2019. See woodstock.com

STAY

Big Pink is available to rent via HomeAway. The owners are very friendly. Ask for a guided tour of the basement; it's likely to be locked. See homeaway.com

Andrea Black travelled at her own expense.

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