An Upstate Journey to Woodstock, New York

Patchworks of nature fill our windshield as we blaze a trail northwards along Highway 87. All around us, swirls of deciduous and conifer trees contrast against harsh limestone faces, reminding us that we are only guests in this place of forest dwellers and craggy giants.

At first glance, the rising Catskill Mountains seem at odds with the rolling farmlands and churning river swells of the Hudson River Valley. Yet it is soon revealed to passersby that these distinctive terrains blend well to create a diverse landscape and lifestyle for those who crave it. Here is a place where new growth and old worlds collide — generations of mountain folk, farm folk, river folk, and city folk  — all seeking their own refuge.

When deciding on the next destination to add to your own travel atlas, the prospect of “having it all” is quite alluring. In Upstate New York, you can bask in the tranquility of a cabin in the forest and then be strolling along a picturesque main street of a river town by lunchtime. No wonder the Hudson River Valley and the Catskills have long been havens for people from the Big Apple. Weekend jaunts transform into “part-time” living and eventually [for some] the big relocation to the country. Upstate NY brings you everything you love about the city — rich in its offerings of eateries, culture, music, history, art and creativity 
— with the added perks of nature and space.

So forget the suburbs and into the woods we go.


The Artist’s Hamlet : Woodstock, NY

The headstone could read:

Here lies a town made famous by an epic music festival that never in fact took place here.

But of course there’s more to the story…

So perhaps this instead:

Here lies a colony for the utopian of heart, all progressive minds are welcome.

Yes, that is more like it…

Indeed, that famous concert gave Woodstock its legacy as one of the world’s most famous small towns and its place on the hippie circuit circa 1969. However, if we reach even further back in recent history, many old time residents were drawn here in search of a mindful respite from the noise and congestion of the urban jungle. What they built was a vibrant, intellectual, and creative community that was the ultimate inspiration for the founders of the Woodstock Music Festival. 

Today, you can find numerous hideaways of novelists, artists, poets, musicians, ceramists, sculptors, journalists, chefs, entrepreneurs, storytellers, professionals, activists, etc. tucked away in the eclectic houses of this mountain settlement. A confluence of gifted individuals gives the Woodstock tribe its unique edge, so whether it be a visit, many visits, or a move, Woodstock has a lot to offer the curious and free spirited.

Starting Point

Puttering down Mill Hill Road in the direction of Tinker Street, you can feel the buzz of the town moving centrally towards the Village Green. An energetic meeting place, the Green will be your first peek into the character – and characters – of Woodstock. From the “Women in Black” standing vigil for peace and justice in the world to “Father Woodstock” a poster child for the flower power movement. As you take a rest on its stone walls, you watch visitors pour out of the confines of Trailways buses from the City. Notice the familiarity of locals and how they greet each other. Hug the Peace Pole. The Green is both a congregation and observation point to soak up some of Woodstock’s energy before embarking on a journey around town.

A good starting point to planning your day(s) is to grab a Woodstock Times from one of the shops. This small town’s “crier,” will get you up to speed on local news and outlines local happenings in its Weekly Almanac. If you still listen to the radio [well at least I do], make sure to tune your AM/FM dial to 100.1 Radio Woodstock for the latest on upcoming events and chatter from in-the-know personalities.

Each of Woodstock’s four seasons bring endless new gatherings, but the true constant to capturing its soul of place is by way of its daily rituals and established traders.

Breakfast Stop

Kickoff your day with a generous breakfast at Oriole 9 on Tinker Street. A local landmark, the restaurant is cleverly named after the historical telephone exchange for Woodstock. While you wait for a table, scrawl a bit of inspiration and reflection on the “Dream” and “Grateful” wall in the entryway. Once inside, first check the colorful daily specials on the chalkboard, as there are bound to be several gems (if you’re lucky you may even score their yummy savory bread pudding). A top pick for coffee in town, also consider stopping by mid-day for a rejuvenating cup at the communal table, who knows who you might meet.
Find it:          17 Tinker Street
Instagram: @oriole9ny

What to Do


If you are an art enthusiast…
stroll around the village and sample the local art scene. From a center for photography to a collective art museum, interspersed with individual studios, a variety of fine art galleries are on display throughout Woodstock. If you have a car, you can find additional artist galleries nestled throughout the surrounding windy mountain roads. However, for a special glimpse into the artistic process and life, visit Byrdcliffe Art Colony on the outskirts of town. A woodland haven for artists of all mediums, this guild hosts exhibitions, classes, workshops, performances, and artists-in-residence.
Find it:         144 Upper Byrdcliffe Road

Nourish your bibliophile side…and find your way into the independent book dealer, the Golden Notebook. A treasure trove of intriguing literary works, pay special attention to the first section of books devoted to local writers and New York escapades. If you are lucky, a visit may coincide with an intimate reading by a famous author.
Find it:         29 Tinker Street

Eat your weight in local food…”If it’s Wednesday it’s Woodstock Farm Festival.” A market devoted to bringing you the freshest bounty from the Catskill/Hudson Valley foodshed, it’s also a great spot to mingle with native Woodstockers and [over] hear about what’s what that week. Open from June – October, rain or shine.
Find it:        6 Maple Lane (in the meadow behind Bread Alone)

For the inner (or outer) hippie…participate in the weekly drum circle on weekends. Bring your own drum or borrow an instrument from the communal box. Release your wild child (and any worries) by dancing to the beats with locals and visitors alike.
Find it:       Village Green

For culture seekers…catch a matinee showing at Upstate Films, a non-profit organization supporting independent filmmakers, education, and public forums.
Find it:        132 Tinker Street

Need to find a minute to zen out
…take a class at Euphoria Yoga, adding the renowned Jivamukti to your yoga 
repertoire. I practiced in this studio for many months and can attest to the intimate and sacred space you find within their community.
Find it:         99 Tinker Street

If you worship Mother Nature…take a day hike up to Overlook Mountain. As you explore the peaceful woodlands, sweep your eyes along the storied forest – floors of fern and moss colonies, dense under stories and canopies of birch, ash, spruce, maple, and beech trees and canopies. Climb the trail to emerge at breathtaking views and the ruins of an old hotel. 

Where to Dine

  • Take a pause in your day and have quick lunch at Bread Alone. From the Catskills through the Hudson Valley down to NYC, this little bakery supplies restaurants and locals alike. Known for churning out delicious breads and baked goods, there is also an assortment of creative sandwiches on the menu.
    Find it:     22 Mill Hill Road
    Instagram: @breadalonebakery
  • Swing by the counter at Sunfrost Farms for a wide variety of freshly squeezed juice concoctions that will refuel your day.
    Find it:    217 Tinker Street
  • Indulge a little with some upscale comfort Italian at Cucina. Perfect for an intimate dinner, grab a glass of vino and sit al fresco on the big wrap around porch.
    Find it:     109 Mill Hill Road
    Instagram:   @cucinawoodstock

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