My First Love in Ulster County, NY
If you’ve ever driven north just to clear your head…
If you’ve ever stood still in the woods and felt like something shifted…
If you crave places that let you slow down and just be, then we might already be on the same wavelength.
I’m someone who feels most at home in nature, who looks for charm in the little things, and who believes that some places carry a kind of magic. Woodstock, NY is one of those places for me. Actually, it was my first real love upstate - the first town I visited that made me think, "Wait, why don’t I just stay?"
Whether you’re a longtime mountain wanderer or just passing through for a day, I put this little guide together to help you experience Woodstock the way I do: fully, slowly, and with an open heart (and maybe a taco in one hand and a cocktail in the other).
A Perfect Day Trip to Woodstock, NY: Peace, Tacos & Firelight
Ah, Woodstock.
The kind of town that gently pulls you in and makes you want to stay forever. Where drum circles break out on Sundays like clockwork, and everyone from barefoot wanderers to cocktail-sipping creatives seems to be humming the same tune of peace, love, and lingering a little longer.
First, Park the Car and Let Go
There’s a great $10 lot right in the middle of town with bathrooms and all-day parking. Plus a bonus of street vendors selling clothes, jewelry & other fun items. Once you’re there, you really don’t need the car again. Woodstock is completely walkable, and that’s honestly part of the charm.
Ashokan Rail Trail- a must do
An 11.5 mile peaceful and easy walking and biking trail that follows an old railroad line along the Ashokan Reservoir. (perfect for walking off breakfast or any meal) Gorgeous mountain and water views the whole way and its dog friendly too.
Optional: Stay at The Woodstock Way Hotel
If you’re turning your day trip into an overnight (and honestly, you should consider it), The Woodstock Way Hotel is my favorite place to stay. It’s tucked into a little nook of the town, steps from the main street but surrounded by trees, with a modern rustic vibe that still feels deeply rooted in Woodstock’s history. Think polished concrete, reclaimed wood, and views of the waterfall that runs right through the property.
Don’t Miss: The Waterfall
Even if you’re not staying at the hotel, make a point to walk down to the waterfall behind Tinker Street. It’s small but stunning, hidden in plain sight. Bring a coffee (or a joint), sit for a while, and just listen. It’s one of those little spots that feels like your own private escape.
Wander the Shops Around the Hotel
Right around The Woodstock Way Hotel, you'll find some of my favorite little shops in town. A few steps up the road you’ll hit:
Treasure Chest Antiques
Vintage Modern
Mirabai Books
Lily’s Boutique
Woodstock Emporium
Candlestock
These shops are small but mighty. You can easily lose yourself for an hour just poking around and soaking it all in.
Taco Lovers
Tucked into Woodstock like a little secret you almost want to keep to yourself, Tinker Tacos feels less like a restaurant and more like a small, joyful discovery. It’s the kind of spot you’d gladly travel miles just to taste again. The lengua and pork tacos are unforgettable and sitting outside at a picnic table, soaking in the easygoing energy, everything just feels right. It’s a true little gem, and every visit feels like coming back to something you love.
Early Terrible
By afternoon, make your way to Early Terrible and settle in for some serious fireside lounging. This cocktail bar is a hidden gem where time slows down. Sip something strong, sink into a chair by the firepit, and take in the moment. Stay as long as you like. No one’s rushing you. It’s a magical spot with small bites and firepits everywhere, perfect even during the Winter and zero pressure to do anything except chill. There is always a great playlist going and I usually give myself at least a couple hours here. It’s the kind of place that feels like it’s always been waiting for you, wood carvings, disco ball and all.
