Deep Newburgh—by deep Newburgh, I mean places like Liberty Street in the heart of the ghetto and by putting it on this list, I’m partially kidding. I mean, if you’re looking for an education into the other side of the Hudson Valley before you go back to your quaint AirBnB, then this is the place to see the heart and soul of a place that has scared the shit out of many an unsuspecting (and even a suspecting) dude. Newburgh has the potential to be truly amazing but deep Newburgh shows just how unamazing, in actuality, it can be.
Gomen Kudasai, New Paltz—the Hudson Valley isn’t exactly flush with great Asian food. Most of the Japanese restaurants are run by non-Japanese and are called things like “Chopsticks” or “Origami.” Gomen Kudasai, though, up in a strip mall in New Paltz, actually has legit good Japanese food. The restaurant’s okaasan has an aura about her that is warm and welcoming in an I’m-gonna-take-care-of-you-and-cook-for-you sort of way. They also have local live music on some nights. Nothing crazy; nothing over the top. Just right.
The Downing, Newburgh—want to see classy movies with the old folk crowd. This is where to go to do it. They have the best movies in the area and you’re in a somewhat comfortable basement by the river with a screen a tad too small. Yet somehow this is the best (and perhaps only) reason to go to the Newburgh waterfront.
Tivoli—this town is straight-up weird. The main street is just a row of Victorian houses with bars and shops in the would-be living rooms. There’s about a thousand people who live in this town and I’m pretty sure none of them wear shoes. I love it.
The Pantry, Cold Spring—I’ve found it much harder than it should be to get a decent cup of coffee in the Hudson Valley. This small beer/coffee/meat shop is just the type of cute, quality place that you’d expect to be all over the place up here. But for some reason, this type of place is rare up here and exactly what the Hudson Valley needs more of.
Oriole 9/Bread Alone, Woodstock—Woodstock can be alternately cool and annoying but these two establishments right next to each other are simply solid places with good food that just so happen to be located in Woodstock. Oriole 9 is great for brunch. Bread Alone is great for, well, bread.
Trevor Zoo, Milbrook—this is a zoo run by high school kids. Seriously, this is a zoo run by high school kids. Even if it was a shitty zoo with a few praying mantises and a rat, I still would’ve included it just because it’s a zoo run by high school kids. But that fact that this place is actually cool with legit wild animals kind of blows my mind. It’s pretty far out in the middle of nowhere so not many people make it out here, but I found it worth the trip.
Antique shopping in Millerton—Hudson gets all the hype, but Millerton is where it’s at for antique shopping. There are just a few places but they’re big and much cheaper than Hudson. It’s a cool town besides the antiques and even has a better than decent coffeeshop in town which is rare in these parts. A pain in the butt to get there, but a surprise treat once you’re there.
Lippman Park, Ellenville—another mountain biking entry here. Overall, this place is really good but what really sets in apart is the serpentine windy beginner trails at the bottom replete with small obstacles and easy bridges. Tons of fun for all abilities.
Basillica Hudson, Hudson—incredible beaten up, somewhat converted barn on the outskirts of Hudson that hosts music venues. It feels like your wandering into some crazy, cultish place that a group of high schoolers discovered and turned into their partying grounds. This place is super weird and super creepy and a great place to freak out if you’re seeing something like Godspeed You Black Emperor which is precisely the weird sort of shit you want to see here.
Ninham Mountain, Carmel—I can’t believe how awesome this place is for mountain biking given how little you hear about it. Both sides of the road are great. I usually stuck to the east side where it feels like just about no one in the world knows about. It feels like you stumbled upon this incredible unknown network of trails somewhere near the ends of the earth.
The Bearsville Theatre, Woodstock—a small, intimate venue in a quaint setting with a brook skirting along the back. There’s a cool little bar inside and a weird little Chinese restaurant next door. Surprisingly good acts come through but it still feels like you’re watching music in a neighborhood barn. In a good way.
Coquito, Warwick—some fancy Puerto Rican food in the least Puerto Rican place on Earth? Yes please!
The Hop, Beacon—this place used to be this little beer/meat shop with employees straight outta Brooklyn. It was the coolest place in all of the Hudson Valley and the best place to buy beer. Then they went and turned themselves into a full-blown bar and restaurant which is still one of the coolest places in the Hudson Valley but they lost something in the way your favorite band loses something when you hear them all over the radio. (I’m looking at you Modest Mouse circa 2004.)
The Farmers Market in Rhinebeck—you’d think farmer’s markets out here would be amazing but somehow they’re not. The Rhinebeck farmer’s market is the exception. A little classier than I like my markets but Rhinebeck is a classy place so it comes with the territory.
The Roundhouse, Beacon—I’ve only ever been here for drinks and snacks but I bet the food is amazing too. And even if it’s not, this place is just so darn cool. It’s this old brick building that seems somewhat precariously perched over a creek at the end of the main street running through Beacon. And sitting outside in the summer with a quaint view of the man-made waterfall with old brick warehouses in the background is a unique experience that can only be found here.
Breakneck Mountain, Cold Spring—want to feel like you never left the city? Come to Breakneck. It’s insane how crowded this hike has gotten in the past ten years or so. But there’s also a reason for it—there’s just something about scrambling up a rock face that reminds you of being a kid. And then standing up top and overlooking the mighty Hudson and West Point across the way. Then just keep on going once you’ve reached the top for a little respite from the masses.
The Peekskill Brewery, Peekskill
Beacon—while everyone blahblahblahs about Hudson, Beacon is actually the coolest town in the Hudson Valley.
Bannaman’s Island, middle of the Hudson—I’m sure a quick Google search of this dilapidated castle on an island in the middle of the Hudson would unlock all the keys to this treasure. But to be honest, I don’t want know. This mysterious structure is the stuff of lore and Hudson Valley legend. I’ve never been on a tour so I can’t speak to that but a kayak ride up close would do the trick.
Blue Mountain, Peekskill—a mountain biking gem. This place is large and technical, alternately flowy and frustrating. It’s general not crowded especially considering is basically the best trails you’re going to find around.
West Point—a fortress on the banks of the Hudson. This is one of those places that people don’t seem to give enough mental energy too. I can’t believe this place still exists and is still so perfect given how the ripples that emerge from this place cause and have caused seismic rifts in distant lands.
Blooming Hill Farm, Blooming Grove—this is what you expect when you come to the Hudson Valley—a farm that sells their stuff out of a big makeshift shack run by a big friendly dude that looks like Santa Claus. You can sit here in the farm behind the shack next to the bubbling brook and drink your damn good coffee and damn good scone or breakfast and think about how lovely it is up here in the Hudson Valley.
Opus 40, Saugerties—Nothing impresses me more than a life dedicated to a piece of art that borders on lunacy. Usually these are out in West. (Arcosanti and Gallery of the Sun are a couple of my favorites.) Opus 40 is this somewhat forgotten about masterpiece of a somewhat insanely obsessive guy who bought a quarry and spent the rest of his life building this gigantic structure out of the stone. It’s humbling and inspiring all at once.
The train trestle, Cornwall—the intersection of Otterkill and Orrs Mills in Cornwall on a hill that overlooks a huge meadow with the Moodna Creek cutting through it and the majestic train trestle in the background makes for the best view in the Hudson Valley. If you’re feeling adventurous, you can cross it, ride your bike across it, or try to climb it none of which are legal and rightly so. When a train comes and you’re on it, it’s terrifying. (Not that I would know.)
Storm King Art Museum, Cornwall—a huge outdoor sculpture garden. Since experiencing the Storm King Art Museum (countless times,) I’m intrigued by every sculpture garden I come across but nothing can come close to the size, creativity, and straight-up grandiosity of this place. You can spend hours here walking the grounds and not see the whole place. Everything here is unlike anything you’ve ever seen, incongruous and harmonious at the same time.
