Where?

Woodstock, New York, US

Why now?

Utter the name of this Ulster County town and it conjures images
of hippy types dancing and singing to the likes of Jimi Hendrix and
Janis Joplin. Held in 1969, when the US was preoccupied with the
Vietnam War and civil-rights protests, Woodstock festival had a
huge impact not only on the music industry but ideas around the
freedom of expression too.

The “three days of peace and music” actually took place about an
hour and a half’s drive away in Bethel, but that hasn’t stopped
Woodstock town from becoming the beacon of eclecticism and free
spirits it is today. Just two hours’ north of New York City, its
streets are lined with local-owned restaurants and cafés, boutiques
and small galleries. It’s also the starting point for one of the
best hiking routes in the Catskills.

Don’t miss

A perfect day in Woodstock looks something like this: wake
early, throw on your hiking boots and trek across Overlook Mountain – at the summit, you’ll gawp
at breathtaking views and happen upon an eerie, abandoned hotel.
Grab lunch at Garden Café and walk the town’s streets –
specifically, Tinker Street – to browse the shops. Come evening,
check out one of the many live music events. We suggest checking
the calendar at Levon Helm Studios.

Where to stay

The Woodstock Way Hotel is perfect for those who
want to tap into the town’s counter-culture energy without forgoing
modern amenities. Choose a room, suite or cabin, all of which are
within earshot of the nearby waterfall.

Where to go for dinner

SILVIA. A recent opening, this restaurant centres its
cooking around a wood-fired grill and locally sourced ingredients.
Couple this with its cosy al fresco set-up, and you’ve got the
perfect upstate dinner experience. Book ahead.

And for a drink…

Set in a restored barn, Early Terrible Wine Bar captures the essence of
Woodstock. It also serves tapas, so if you’ve bagged a cool spot
here and don’t want to lose your spot to get dinner, you’re set for
the night.

Most likely to bump into…

It has been remarked that most of the people you run into here
don’t realise that the 1969 concert happened more than 50 years
ago. Expect to bump into friendly hippies eager to reminisce about
their youth.

When to go

It’s best to travel here during the summer months. In the warmer
temperatures, you can take advantage of the hiking, swimming in
nearby watering holes such as Fawn’s Leap, along with live outdoor
music.

Essentials to pack

As you’ll spend most of your time outdoors, bring along your
favourite sunnies – we like this retro pair by FreshForPandas.

How to get there

We recommend renting a car to make the most of Woodstock’s
surrounding nature. If this isn’t an option, take an Amtrak train
from Penn Station, NYC to Rhinecliff – from there it’s a 25-minute
taxi ride.