Feeling groovy on a retro-inspired trip to Upstate New York

Just over half an hour on the road south-west, my playlist having reeled through the sounds of Neil Diamond, Janis Joplin and Hendrix, I reach the Catskills’ musical epicentre, Woodstock.

Clients can catch live bands most nights at the aforementioned Colony, the place where Bob Dylan and members of The Band would get up unannounced and drunkenly play Americana tunes. Manager Mike wants the club’s latest incarnation to capture the diverse artistry that pervaded Woodstock long before – and after – the three-day festival. “There’s a lot of youth moving to the area. Our programming caters to that audience, as well as those who moved here in the aftermath of the 1969 festival and never left.”

Colony’s location, Rock City Road, is one of this tiny town’s three main veins of clapboard vintage shops, bars and cafes, emanating from one leafy centre. Free thinkers and peace crusaders prevail, with “Immigrants and Refugees Welcome” window flyers tacked among posters for tarot workshops.

At Rock City Vintage, an emporium of cool and colourful garb, I can’t resist making a patchwork woven jacket my own. It’s also worth clients dipping into the free gallery of bold canvas paintings and surreal human sculpture by the Woodstock Artists Association, which celebrates its centenary this year.

Next, I rewind some years at Station Bar & Curio. Shelves are laden with eclectic thrift-shop objects, while bearded locals engaged in lively conversation prop up the bar. A fringed leather jacket-wearing old rocker is happy to pose for selfies with me, peace signs obligatory.

A couple of miles out of town on Maverick Road, Hotel Dylan – slogan “Peace, Love, Stay” – captures the spirit of the 60s without being stuck in the past. With a record player and vinyl in every room, the songs transport me to the scenes in the framed retro photography of bikers and festival goers on the walls. Weekends here bring live music to the lobby, where clients can swig beers on chairs that swing from the ceiling.

After a taste of rock star-style hedonism, it’s time to discover the area’s spiritual side. Overlook mountain, gateway to the Indian Head Wilderness, is a 15-minute drive away. At the trail entrance stands one of the largest Tibetan monasteries in the US. Ringed by brightly coloured cloth prayer flags, it’s open daily to the public for meditation.

I set off into the silent remoteness, following a dusty track five miles there and back. Startlingly, out of the mist appears the shell of a 1920s hotel. A ghost from the Catskills’ golden era of grand mountain resorts, birch trees twist through this relic that burned out long ago.

It’s only from the 914-metre high peak (or the top of a historic fire tower, if you dare), that you get a true sense of height. With a layer of mist shifting rapidly over the forest below, it’s no wonder this spot was once identified by Native Americans as home to great spirits.

In these parts, rural beauty often has a bohemian heart. My last stop of New Paltz, a university town 40 minutes from Woodstock, borders the flower-flecked meadows of the Mohonk Preserve. Students mingle in the galleries and record stores of the high street; a dash of youth the perfect partner to laid-back hippy roots.

Back in the big city before my flight home, in low-lit Mexican restaurant Gordo’s Cantina, I tell a New Yorker on the stool next to me of my adventures. He asks me: “Why would you want to go up there, when you have all this here?”

I reply that a metropolis will always hand you experiences on a plate, but the discoveries you make for yourself upstate – the eccentrics and creatives, the spirit-stirring wildernesses, an inventive cocktail bar beside the woods – that’s real adventure in my book.

Book it: America As You Like It offers a seven-night trip to Upstate New York from £1,435pp including flights, three nights at the Wolcott Hotel New York City, two nights at A Tiny House Resort in South Cairo, two nights at the Hotel Dylan in Woodstock and car hire. Based on two sharing.

For more information visit: americaasyoulikeit.com; sullivancatskills.com; greatnortherncatskills.com; ulstercountyallive.com

Smarter: Most attractions in New York State are open year-round except May, which has two annual holidays: Memorial Day and Labour Day. Recommend visiting attractions mid-week rather than on weekends to avoid crowds.

Better: For families visiting the Catskills seeking fun, suggest a day trip to the Zoom Flume Water Park (zoomflume.com).

Fairer: Chain restaurants are minimal in the area, so encourage clients to eat at local restaurants to give back to small businesses.