A visit to Woodstock, New York, is like going back to a different time. It’s not just the fact that the town is (understandably) stuck in the classic rock era. It’s listening to Radio Woodstock while you’re driving Levon Helm Memorial Highway. Each souvenir shop has memorabilia galore, from clothes to posters of all your favorite 60s and 70s era bands, but that doesn’t fully describe the vibe. It is like streaming music doesn’t exist. It’s the pro-Israel and pro-Palestine demonstrators next to each other, without any problems. It’s the real hippies that still call the town home. An afternoon in Woodstock will be a bit slower-paced than everywhere else. Let’s take the trip, man.
An Afternoon in Woodstock
I met up with an old friend and my afternoon in Woodstock began at Oriole 9 for a brunch of avocado toast. With a poached egg and plenty of arugula, it was a great way to start the day. Other than walking and exploring the town I did something that I haven’t done in about ten years: shopping. I’m not talking about going out and buying something I need and quickly leaving, but instead going into store after store and browsing. (Can’t you tell the kids weren’t in tow?)
Like any touristy town, many of the stores sell the town itself. Woodstock does this four-fold, both with merchandise of the town itself and that of the famous festival, but also of the bands and artists related to Woodstock such as Jimi Hendrix, Bob Dylan, and Led Zeppelin (whether they played Woodstock or not). Finally, it also sells hippy culture; think of incense wafting from inside a store or love beads for sale.
Rock ‘n Roll is Here to Stay
During the afternoon of my visit, there was a flea market. The flea market sold many handmade crafts, vinyl records, and movie and music memorabilia. Perusing the vendors, a few of the salespeople completely fit the stereotype, actually using words like “groovy” and giving a vibe that the summer of 2024 was the Summer of Love.
Shops with names including Strawberry Fields and Not Fade Away paid homage to rock and roll associations. Others such as the Woodstock High Novelties, focused on a subculture often concurrent with the hippy scene. Also close to town is the Woodstock Cemetery where two of The Band members are buried: Levon Helm and Rick Danko. Newly deceased, Garth Hudson, is buried across the street at the Woodstock Artists Cemetery.
If you’re staying the night, Woodstock Way Hotel is my recommendation. It’s a mix of treehouse meets condominium. The rooms are tastefully decorated and the facade is attractive but at the same time blends into the woods, making the nature outside the focal point of the room as the hotel camouflages itself into its natural surroundings. It also overlooks Woodstock Waterfall Park, a serene cascade just off the main drag.
Leaving Woodstock
Before leaving town I had to try the award-winning Peace, Love, and Cupcakes where a carrot cake cupcake was on the menu and quite delicious. I picked up Woodstock festival t-shirts for myself, my wife, and my youngest son.
I hadn’t been to Woodstock in over 20 years and thoroughly enjoyed my visit. Expanding not far over the New England border into New York made for an excellent Backyard Road Trip. For my route, I decided to forgo highways (mostly) and once west of Hartford, it was all back roads for me. Northwestern Connecticut and over the border into New York proved to be ripe for excellent exploration, a region I’d like to come back to as the towns of Kingston and Rhinebeck struck me as places I should return.
It must be a Woodstock thing because no matter if you’re in New York, Vermont, Connecticut, or New Hampshire, check out Woodstock. It’s worth at least an afternoon visit.
