Our trip to Woodstock began with an hour long drive across the Hudson and up I-87, which took us through woods and small towns, and eventually to the base of the Catskills where Woodstock is nestled. Even the drive tells you something about Woodstock: it is rural, small, and surrounded by beautiful forests and mountains. As we passed through West Hurley, a small town right outside Woodstock, I noticed an interesting combination of businesses along the road amidst the woods. There was a simply-built Dollar General, and next to it was a fancy but rustic looking shop called Cheese Louise, which advertised “voted #1 cheese and caviar”. This juxtaposition of upscale and more working class, old and new, nature and human settlement, and outsider vs. locals really represents the atmosphere, history, and economy of Woodstock.

We drove through the town of Woodstock and stopped in small and spread out Bearsville by the Bearsville Theater, which happened to be next to the headquarters for 100.1, Radio Woodstock! A group of musicians, guitars in hand, were just coming out of the studio when we pulled in. Later, we heard their folksy live recording on the radio! We walked down to the Sawkill stream and put our feet in, where Professor Nevarez commented, “there’s probably been thousands of acid trips right here, guys!” The grave of Albert Grossman, famed folk music manager, was nearby. I took a picture and sent it to my mom, who grew up on Bob Dylan, and she couldn’t believe it. The stream and woods around it were very peaceful and pastoral, with the sound of water bubbling and sunlight filtering through leaves.

We met up with Josh Colow, a Woodstock native, who wore a beat-up leather jacket, a warm smile, and who introduced himself as a “hippie for hire.” We drove a little ways up into the Catskills along winding two lane roads to get to his childhood home, an idyllic but rustic white house with an old red barn next door. Josh told us his sister owns the house now and uses it occasionally, but mostly rents it out on Airbnb, where it’s usually booked up solid. Josh, a musician, moved here as a boy with his artist parents in 1969 (the same summer as the Woodstock festival) and has called Woodstock home ever since. As we walked along the road to the sound of crickets, Josh told us about fond memories playing in the woods or stream all day with the neighborhood kids and how music was a big part of his, and everyone’s, lives in Woodstock. We saw a house along the stream that used to be an old mill, and in fact still had the 35 foot tall mill wheel inside. Most of the houses seemed to capture that same vibe–maintaining the simplicity and focus on nature of bygone rural life, and now supporting not farmers or millers, but wealthier, mostly outsider artists and musicians looking for quiet and community.

Josh helped us jump the guardrail to get to some well-loved wooden stairs leading down to the stream. We ignored the “Private, No Trespassing” sign since Josh said that’s just to keep it from getting too crowded, as some of the nearby swimming holes have become. This was probably my favorite part of the trip. We all took our shoes off and spent an hour exploring the stream and getting some quality nature time. The water was super clear and a little chilly, and the stream bed, made of slate and other rocks smoothed by time, had all sorts of interesting pools, waterfalls, and even a natural waterslide! Some people waded up the stream and explored, some climbed rocks and found a nice place to sit for a while, and everyone took lots of pictures since it was so pretty!

After a long while hanging out in the stream, Professor Nevarez decided that it would be good if we got to experience the actual Town of Woodstock itself, and we drove from the hillier part of town (where Josh’s house was) down to a parking lot near the center of town. On the way, we drove through an area that is perhaps best described as a hybrid between a neglected rural area and a tony getaway: some houses appeared run-down (I saw a collapsed bridge in one backyard) while other houses appeared more newly renovated with flourishing gardens and shiny SUVs out front. The only street sign I caught said “South Byrdcliffe Road”, the name a leftover from the Byrdcliffe artist’s resort founded by Ralph Whitehead in Woodstock’s early days. After walking from the parking lot to a spot right in front of the town’s one-room tourism office, we were sent out to explore at our leisure. The town itself is very tourist-friendly and pleasant to visit, which is perhaps to be expected considering it has almost as many TripAdvisor reviews (4,985) as residents (5,884 as of the 2010 census). The first thing Clare and I did was check out the real estate listings. We were impressed by how nice the houses for sale looked for the price (for me especially coming from the crazy real estate market of Greater Boston) and amused by the overall quirkiness of the houses for sale, including a converted doctor’s office and a house that is the “original Brothel of Bearsville” according to local legend.

Across the street was a small shoe store called Pegasus Footwear that reminded me of a similar shoe store in my hometown, with a wood-paneled interior, limited floor space, and shoes for all kinds of activities and uses. Most notable were the pair of Chacos displayed prominently in the window that sported Grateful Dead dancing bears along the straps, designed exclusively by Pegasus Footwear themselves. Even though the music festival itself happened 75 miles away, I thought that the Chacos in some ways represented the present character of the town itself, as a combination of an appeal to the nostalgia of the Grateful Dead days and an appeal to stylish, outdoorsy young people. (Though few people might call sandals “stylish” with a straight face, Chacos in particular are quite popular these days!).

I also got the chance to visit Bread Alone bakery, whose bread was featured in the old Vassar dining hall but has sadly been discarded by the new dining service provider. The bakery also had a wide variety of pastries, baked goods, sandwiches and coffee available; if I couldn’t see outside I might have mistaken it for a coffee shop in Manhattan! The crowd in this bakery tended on the younger side, and I got the sense that Bread Alone was definitely trying to appeal to a young and hip crowd visiting from somewhere else (though liking good food is not of course limited by age or geographical area!). After visiting a few more stores we piled back into the van and got back on the road to Vassar. Overall, our visit to Woodstock couldn’t have been more lovely: we were able to experience the rustic parts of town up and away from the bustle, adventure in a few different streams, and get a sense of the tourist experience as well. Woodstock is at an interesting spot, between a hippie heyday and a potential new boom as more and more city-goers seek an escape, but its beauty and charm will hopefully keep it attractive to visitors of all stripes for many years to come!

John and Clare