As a teenager, I would dream of being able to attend the 1969 Woodstock festival. I watched all of the documentaries and listened to Jimi Hendrix and Janis Joplin. I even wore some very questionable outfits, just trying to get closer to the time of “peace and love”. Visiting Woodstock would have been a dream come true back then.
These old high school fantasies are what inspired me to finally go to the town of Woodstock, which I already know, isn’t where the festival ended up being held. Still, I drove to that little New York town 3 years ago hoping to get a little taste of hippie culture, and it was everything I dreamed it would be.
It’s was so nice, that I drove back again this past summer, right after we spent a wonderful day in New Paltz ,a town about an hour away. Both of my trips to Woodstock lasted just a few days, and were filled with exploring and fun. This guide will help you if you’re thinking of visiting Woodstock!
Where to stay
Both times we’ve been to Woodstock we have been on a super budget. Which means we stayed at a chain motel about 20 minutes away. But if you can swing staying in the actual town, there are some really awesome hotels and inns that we’ve walked by, with dreams of staying there one day. The Woodstock Inn on Millstream would be my first choice for somewhere to stay. It is the definition of cozy. We drove by, and I made my fiancé turn around so we could drive by again. I looked at the pictures and reviews before hand, and just loved the vibe of the place. It’s pretty affordable for most people at under $150, so if you can, I suggest staying there!
Another cool option is the Woodstock Way Hotel. This hotel reminded me of the cool woodsy houses in Oregon. With big open windows and a tall wooden structure, this place feels more like a cool Airbnb than a hotel.
What to Eat
There are a pretty good amount of food options for this being such a small town. A great budget option is Marias Balazaar, which we ate at both times we visited Woodstock. It’s a deli, that serves delicious hot food as well and has really peaceful and quiet outdoor seating. It’s a diamond in the rough before, plus the people are really nice.
Tinker Taco Lab was closed both times we visited, but I drooled over the menu and pictures on Instagram. They’re only open on the weekends, and we always travel during the week, but if you’re there between Friday and Sunday, get there. People absolutely love it and I only wish I could have had 1 or 20 tacos from there.
In the mornings, and early afternoons, everyone and their mom was at Bread Alone. When you walk in, your mouth will water because of how delicious everything looks. They keep all their cookies and muffins on display so beautifully. It’s gorgeous in there and you can tell it’s a local favorite.
The Mud Club is the last notable food place I want to suggest. I’ll be honest and say I was too intimidated to go into here. It looks kind of fancy, but also private, even though it’s on the main strip and next to a popular pizza place. I thought it was too legit to me (a habit I need to get out of) but it turns out that it’s a bagel shop! I was too afraid to go into a bagel shop! The building looks like an old time cabin, but it’s also pretty big. And from the pictures online It looks nice and cozy and freaking delicious. I’m gonna go next time!
Shindig is a cool local eatery in the center of town that does breakfast, lunch, and dinner with locally sourced goods. Its homey and overlooks the town square, kinda like a Luke’s diner (from Gilmore Girls)!
*Farmers Market – If you’re in town on a Wednesday in the summer or early fall months, check out the farmers market! It’s full of fresh local fruits and veggies, as well as local artisans and vendors.
Drink it up
I’m always looking for a juice or smoothie bar, and the one in Woodstock is really nice. It’s called Little Apple, I went both times I visited and loved it. They’ve got delicious fresh vegetable juice, açaí bowls, organic frozen yogurt and it’s all really affordable!
Station Bar & Curio is the spot to go in Woodstock for drinks and live music. It’s at the very end of their main street (Tinker Street) and has a homey vibe, like you’re drinking in a really nice person’s living room. It’s also right next to an ice cream shop, which is unrelated but still very exciting!
Where to Shop
There were so many awesome, tiny, local business in this small town. I’ll start with my favorite which was a place called Woodstock Bring Your Own. This spot has all of your sustainable needs, like metal straws, local soaps and lotions, kids books about helping the planet, bulk items, the list really goes on. I wanted to buy everything.
Down the street from that shop the wonderful indie bookstore in Woodstock, Golden Notebook. Since I write for IndependentBookReview.com, I’m always searching for a great bookstore and Golden Notebook did not disappoint. They had a good variety, a homey feel, and a nice selection of indie books.
There were a few stores that sold really great clothes and gemstones, like Tibetan Arts and Crafts and a store that’s attached to the Village Green Bed and Breakfast, whose name i can’t remember. I love finding cool new stones and blankets from stores like these, and they both had a really large variety and knowledgable staff.
Little House acts as the cool hipster general store on the town. They have the things you’d want to buy for your dream house like awesome mugs, rugs, and wall decor. They have lots of local crafts and the gifty items you’ll buy for someone else, but secretly want for yourself.
There are, of course, very many hippie shops with drug rug sweatshirts and Woodstock t-shirts. They were all really nice, and had a lot of the same or similar stuff so any of them that you visit will give you the “I’m in Woodstock!” feeling. They’re good places to buy souvenirs from.
Things to Do
Woodstock is also home to a Tibetan Buddhist Monastery. Founded in 1976, the Karma Triyana Dharmachakra Tibetan Buddhist Monastery opens it’s doors to the public for a peaceful and interesting visiting experience. Not many places have Tibetan Buddhist Monasteries, so it’s definitely something to see if you’re in Woodstock.
If you want to get out into nature, you can take some awesome hikes while visiting Woodstock. Woodstock is conveniently located right in the Catskill Mountains, which has some of the most beautiful scenery in the state of New York. Overlook Mountain sits kind of on the edge of town, but has some amazing views and is worth the trip. It’s 4.6 miles out and back, so it’s a nice little workout if you’re up for it.
Visiting Woodstock was so fun for me both times. You can tell they have a strong community, from how kind and helpful the locals are, and that they pride themselves on being known for the festival. Take a trip up there to get a taste of the “peace and love” the town has to offer. And while you’re in the area, check out some of the other cool towns in upstate New York!