The Steele Maiden: Travel Guide to Upstate New York

This October, Adam and I finally decided to go find out what New Yorkers rave about every Fall: Upstate. The results? We’re hooked. Just a 2 1/2 hour drive from our city stoop you get a much needed escape into nature (hellooo foliage) and small town charm that’s very reminiscent of New England this time of year. Plus, (thankfully) still delicious food and drink. In short, we’ll definitely be back. Below, my greatest hits from the trip and what I already can’t wait to try on our next trip.


Most places in the Hudson Valley are about a 2-3 hour drive from New York City making it the perfect weekend (or mid-week!) escape. We hopped from town to town (Windham, Woodstock, Phoenicia, Saugerties, Germantown and Hudson) throughout our stay and most of them are about a 30 minute drive apart.

The Steele Maiden: Travel Guide to Upstate New York


We stayed at Eastwind Hotel & Bar and while it was our first trip upstate, I honestly can’t imagine staying anywhere else. I’ve mentioned before that I like to stay places that feel really unique to the area and with it’s rustic, mountain charm meets cool mid-century design the Eastwind embodied how the Catskills felt to me. The common area boasted a wood-burning fireplace, vintage board games and the quaintest little bar, the property had a wooden sauna, badminton on the lawn and shared fire pit for guests at night and the rooms were swoon-worthy in every corner. We stayed in one of the King rooms, but you can also stay in a tiny A-frame cabin that offers the chance to wake up to mountain views. The whole place is honestly just gorgeous and felt really welcoming. I can’t wait to go back up when it’s all blanketed in snow this winter (ps. they’re even putting in a hot tub soon that’s going to set the whole cozy level over the top).

The Steele Maiden: Travel Guide to Upstate New York The Steele Maiden: Travel Guide to Upstate New York The Steele Maiden: Travel Guide to Upstate New York The Steele Maiden: Travel Guide to Upstate New York


The joy of escaping the city and surrounding yourself with nature is that you can really just slow down. So if you want to simply sit and play games in front of a fire at the Eastwind with mountain views out the window, you should do just that. But if you want to do some exploring, there’s plenty to keep you entertained.

Go Leaf Peeping – There’s plenty of paths throughout the Catskills that are going to offer sweeping views and great hikes – but if you want to take a little shortcut, Hudson Mountain uses their ski lifts in the off season to take you on a leaf peeping ride straight to the top (runs weekend’s only through mid-October). Or simply take a scenic drive – we loved the Five State Overlook in East Windham.

The Steele Maiden: Travel Guide to Upstate New York

Shop Small – Hudson, Woodstock and Saugerties all have endlessly cute little main streets (although Woodstock’s comes with a predictable amount of tie-dye t-shirt shops). I loved the selection of mid-century housewares at Vintage Modern on Tinker Street in Woodstock.

Saugerties Lighthouse – A short little hike out to this lighthouse for pretty views on the Hudson. Don’t forget to check the tides though, you won’t want to get stuck out there with rising waters.

The Steele Maiden: Travel Guide to Upstate New York

Buy a Book – You all know I love a good independent book shop and when we travel I almost always seek one out so I can pick up a book as a souvenir. There was not one but two great shops on this trip: Spotty Dog in Hudson which is magically both a bar and a bookstore and truly like the place of my dreams. And Inquiring Minds in Saugerties which also has a cute little cafe in the back, areas for reading and a record section.

Visit a Local Farm – We didn’t have time to make any stops but I’ve heard good things about Fishkill or Greig Farms.

The Steele Maiden: Travel Guide to Upstate New York


The joy of eating and drinking in Hudson is that many places were started by New Yorkers – meaning the food and drink holds up to our impossibly high standards of deliciousness here in the city. So you get to escape into nature.. but still eat like you’re in the city. Win, win.

Cucina Woodstock – Set in a beautiful old manor house with a sweeping wrap around porch, dinner here feels instantly romantic.

Suarez Family Brewery – Between Hudson and Germantown this small craft beer brewery is a great little stop off with a few beers on tap and plenty of tables for hanging out. Give a pat to the cute shop dog for me if you go, we were fast friends.

Phoenicia Diner – Kind of iconic at this point, it’s basically like if the East Village went upstate. A hipster-haven/old school diner that served up solid food (the potatoes and pancakes were our favorite).

The Steele Maiden: Travel Guide to Upstate New York

Shindig – Great little lunch spot in Woodstock on Tinker Street.

Miss Lucy’s Kitchen – Maybe our favorite meal of the trip this tiny little spot in Saugerties feels like home cooking.. but elevated. Make a reservation or come early – on a Friday night we got lucky and squeezed in as the last seats available.

Fish & Game in Hudson and Gaskins in Germantown were both highly recommended to us by friends and Eastwind Hotel as well and on our next trip I hope to try them both!

Don’t forget to pick up an apple cider (or 6) from one of the many farm stands or mom and pop shops for the car ride home! Until next time!

The Steele Maiden: Travel Guide to Upstate New York