Woodstock Music and Art Festival

Leaving West Hartford

I left West Hartford early this morning, opting for the winding beauty of the backroads over the monotony of the interstate. There’s something more authentic, more connective, about watching the landscape shift slowly around me. My route would eventually take me to the site of the Woodstock Music Festival in Bethel, New York, but the journey itself was half the joy.

I pulled into a Stop & Shop in Canaan, Connecticut, to pick up a few essentials for upcoming meals. With my camper van now fully operational, I don’t need to rely on roadside diners or hunt for coffee shops. In less than five minutes, I made myself the perfect shot of Lavazza Italian Roast espresso—hot, bold, and exactly how I like it. It’s moments like this that remind me of the incredible upgrade from the Subaru to the van. Cheaper, faster, and far better than rolling the dice on whatever coffee a small town might offer.

As I made my way westward, several towns caught my attention. Salisbury, Connecticut, stood out with its blend of charm and modern touches. The town center was lined with boutique shops and cafes, framed by rolling hills that hinted at the Berkshires just to the north. A few modernist homes peeked from behind stone walls, a juxtaposition of old New England and contemporary wealth. I didn’t stop, but Salisbury is bookmarked for a return visit.

Crossing into New York, I passed through Stone Ridge—a town that exudes quiet affluence. The streets were dotted with fieldstone homes, well-tended gardens, and cafes that seemed tailored for long, thoughtful breakfasts. The restaurants and brunch spots here were clearly curated, not just serving food but an experience. Stone Ridge felt like a place where people come to live deliberately—and spend generously.

As I neared the Catskills, the scenery shifted. Streams crisscrossed the roads, and rustic shops began to appear, clearly designed for tourists and weekenders. The mountain air sharpened. The trees thickened. And just like that, I arrived in Bethel.

Woodstock Music & Art Fair

The site of the 1969 Woodstock Music & Art Fair, Bethel Woods Center for the Arts now stands as both a concert venue and a living monument to one of the most culturally significant events in American history. The original festival was never actually held in Woodstock—it was relocated last minute to Max Yasgur’s farm in Bethel when permits fell through. Despite the chaotic start, it became a symbol of peace, music, and countercultural revolution.

The Various Planned Location for the Festival

Make it stand out

The museum itself is beautifully curated, with multimedia exhibits that dive deep into the social upheaval of the late 1960s. From the Civil Rights Movement to Vietnam protests, from psychedelic art to the birth of music festivals as we know them, the exhibits paint a vivid picture of the era. I spent hours inside, taking my time to read, watch, and listen.

Outside, I followed the augmented reality tour, walking to different markers that indicated where key moments of the festival occurred.

Looking Down from the Top of the Festival Grounds

One marker in particular drew me in: the site of the original stage. Standing there, with rolling fields in every direction and the ghosts of 400,000 young people in the wind, was surprisingly emotional. Maybe it was the scale, maybe the symbolism, but I stood there longer than expected, trying to imagine the energy of those three chaotic, muddy, musical days.

Back To The Van

After nearly four hours immersed in history, I returned to the van and spent some time on an ongoing project: organizing the space more efficiently. The sun had started to dip below the tree line, and I was waiting to head to my Harvest Hosts stay for the night.

I noticed several other camper vans scattered around the museum parking area—fellow travelers drawn to the site, just like me. It felt like a shared pilgrimage, each of us chasing a bit of that 1969 spirit in our own way.

First Harvest Host Stay

Around 6:30 p.m., I made my way through a maze of backroads and a three-mile stretch of dirt to reach the property. My host, Chris, greeted me with the easygoing energy of someone who’s lived life on the road. He recently sold his property and was now renting an apartment above the garage—a temporary rest stop, it seemed, before hitting the road again.

We talked for over 90 minutes about travel, camping, and the freedom of this lifestyle. I gave him a full tour of the van, and his eyes lit up at every feature. You could tell: he missed it. The road calls in a voice that’s hard to ignore once you’ve answered it before.

I climbed into bed that evening feeling connected—to history, to people, and to the journey itself.

This is what the road offers, and why I continue to follow it.