By Cleo Vivas-Rojas
There are places that call you back again and again. For me, Woodstock, New An Escape to Woodstock: Rediscovering an Artistic Town in the Catskills
There Is Something About Woodstock
There are places that call you back again and again. For me, Woodstock, New York, is one of those places.
During the Fourth of July weekend, some friends came to visit, and we decided to spend the day exploring this iconic Catskills town. It wasn’t my first visit—in fact, I’ve been there several times over the years, and there was even a time when I seriously considered moving there.
Woodstock has always had a special place in my heart. I fell in love with its hippie shops, laid-back atmosphere, street musicians, small art galleries, and unmistakable free spirit. To me, it has always embodied freedom, peace, love, creativity, and a touch of the beautiful madness that made the 1960s unforgettable.
A Town Built by Artists
Most people associate Woodstock with the legendary 1969 Woodstock Music & Art Fair, although the festival itself took place about 60 miles away in Bethel, New York. Long before that historic event, however, Woodstock had already established itself as an artists’ colony. Since the early 1900s, painters, sculptors, writers, musicians, and photographers have been drawn to the town, creating the creative spirit that still defines it today.
Something Felt Different
When we arrived, I almost immediately had the feeling that something was different. At first, I couldn’t quite put my finger on it, but I knew Woodstock felt different from the town I remembered.
The first thing I noticed was that the little taco and ice cream shop was gone. I remembered Woodstock having just a taco place, a corner burger restaurant, a small bakery, and maybe one nicer grill. Now, several sophisticated restaurants and stylish cafés give the town a much more upscale feel. I also missed the psychedelic storefronts overflowing with tie-dye clothing, artwork, posters, and quirky souvenirs. There seem to be fewer of them today, or at least they are not as exuberant as they once were. I also missed the life-sized Blues Brothers statues sitting outside of one shop, surrounded by colorful artwork and sculptures.
Wandering Along Tinker Street
Walking along Tinker Street, is still a pleasure. Independent cafés, boutiques, souvenir stores and colorful storefronts invite visitors to slow down and simply wander. Of course, every store became another opportunity for our little tradition: searching for magnets and stickers to add to our travel collections. I couldn’t leave without buying at least one of each.
The Town Keeps Changing
Eventually we wandered into one of the stores packed with artwork, photos, gifts, and handcrafted pieces. Knowing how easily I can be tempted to buy something, I let my friends continue browsing while I stayed outside admiring the building.
As I stood there, I recognized the building from previous visits. It had once been home to the Center for Photography at Woodstock, one of my favorite stops in town. Later, while researching this blog, I learned the organization had relocated to nearby Kingston, reopening in 2025 as CPW (Center for Photography at Woodstock).
From a distance, I also spotted the Woodstock Artists Association & Museum. Since my friends aren’t big museum enthusiasts, I decided to save that visit for next time.
Music, Coffee, and a Break from the Heat
It was a very hot summer day, which made strolling through town a little more challenging. In the town square there were two young troubadours performing songs from the 1960s. Somehow, listening to music from that era in Woodstock felt perfectly appropriate. Even today, music remains part of the town’s identity, with live performances filling cafés, parks, and festivals throughout the year.
Needing a break from the heat, we stopped at a cozy café for pastries and cold drinks. My friends ordered smoothies while I enjoyed an iced coffee and plenty of water. We shared a brownie and a delicious apple crumb pie à la mode before continuing our exploration.
As we continued exploring, I noticed the Woodstock Film Festival building for the first time. A reminder that Woodstock’s artistic spirit is still very much alive.
The Souvenirs We Remember
The entrance to the parking area also felt quieter than I remembered. In the past, several local artisans sold handmade crafts there. This time, only one vendor was selling tie-dye T-shirts, sweaters, and handkerchiefs. And yes, I bought one bandana to keep my hippie soul alive 😊
Unfortunately, we didn’t make it to the small flea market, one of my favorite stops in Woodstock. Years ago, I bought two beautiful handmade greeting cards there from an artist with cerebral palsy. Sadly, they were ruined by a leak in my apartment, but they remain some of my most treasured souvenirs.
Although it was one of the hottest days of the summer, it turned into exactly the kind of escape we needed. Even on a busy holiday weekend, Woodstock’s relaxed pace invites you to slow down and enjoy the moment. Sometimes, a day surrounded by mountains, art, and nature is all it takes to recharge before returning to the fast pace of New York City.
Maybe Woodstock Changed…Or Maybe I Did
The town feels a little more polished and sophisticated than I remember, as if the hippie generation grew up while still holding onto its creative spirit. Yet its artistic soul, welcoming atmosphere, and appreciation for music, culture, and self-expression are still very much alive.
Sometimes we all need to step away from the noise, deadlines, and fast pace of city life. Even if only for a day, Woodstock offers that opportunity to slow down, breathe deeply, and reconnect with ourselves. I left feeling relaxed, refreshed, and already looking forward to my next visit.
Plan your Visit
- From NYC to Woodstock:
- Drive via the NYS Thruway (I-87 N) to Exit 19 (Kingston), taking about 2.0 to 2.5 hours.
- Bus: Direct bus service is available on Trailways, dropping you right off in the heart of town at 4 Mill Hill Road.
- Train & Taxi: Take the Amtrak or Metro-North from NY Moynihan Train Hall at Penn Station up to Poughkeepsie. From there, you’ll need to arrange a taxi or rideshare for the 45-minute trip to Woodstock.
Have you ever visited Woodstock? If so, what made the biggest impression on you? Tell me in the comments below. Follow my adventures on Instagram and Facebook for more NYC discoveries!
Visit • Travel • Explore — Everyday magic is just around the corner — let’s go find it.
Photographs by Cleo Vivas-Rojas