I know every New Yorker has already hiked the Catskills or planned a cute little daytrip in the Hudson Valley at some point in their lives, but I’m bored and have now been to this region ten times (including four overnight trips), so I have a few tips for anyone who might want some recommendations. I love the Catskills and the Hudson Valley. As someone who loves hiking and eating, I’ll take this region over the Hamptons any day. The Catskills refers to the mountain range on the west side of the Hudson River and is a haven for artists, musicians, and writers. There’s some good hiking here and the Catskills is probably one of the best places to visit in the fall. The Hudson Valley refers to the region right along the Hudson River and has a long agricultural history, which is why every single meal I’ve had in this region has been incredible. A car is pretty necessary because there are so many towns you’ll want to explore, so many hikes to start in the morning, and so many farm stands on the side of the road to pick up apple cider donuts. It’s a quick drive from NYC, just about three hours, so you can squeeze this into any weekend.

Stay

The most ideal place to stay is my friend’s cozy 2-bedroom cabin with a fireplace, wraparound deck, and second-floor loft. Anthony and I were guests last fall and I couldn’t stop taking photos. She and her husband bought this cabin in the middle of the woods and restored it beautifully. It’s surprisingly affordable to rent on Airbnb, but due to COVID-19, it’s not available until next spring — but bookmark it for later! You’ll thank me.

Since that cabin’s not available right now, the next best place to stay is a B&B in one of the towns like Woodstock, Hudson, Kingston, or Saugerties. My friends and I stayed in a fun B&B in Woodstock called Twin Gables of Woodstock. This three-story home, owned by a couple of artists originally from Brooklyn, was exactly what we wanted from Woodstock: tasteful but quirky décor, a meditation room in the attic, a fire pit to roast marshmallows in the backyard, and the ideal location right on the main strip.

Eat

You’ll eat well in the Catskills and the Hudson Valley. It’s almost impossible not to. Perhaps my favorite restaurant in this region is Miss Lucy’s Kitchen in the quaint town of Saugerties. I ate at this farm-to-table restaurant twice in one week just because everything is so well done, from the grilled hangar steak with carrot risotto cake, to the roasted duck breast. Call for reservations.

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Other restaurants to try:

• Silvia in Woodstock for innovative Korean-inspired farm-to-table food (thanks to a Korean chef!). I loved my grilled octopus with charred sweet peppers and mushroom lentil pâté with pickled vegetables. Definitely make reservations because this is one of the hottest restaurants in town. We made reservations but still had to wait about 15 minutes to be seated because it is that popular.
• Backbar in Hudson for Malaysian-inspired small dishes. I loved the cumin spice tots and black pepper wings with fish sauce glaze.
• Lunch Nightly in Kingston for sandwiches. I’m not even a sandwich person, but the turkey sandwich with cheddar, balsamic lettuce and pickled red onions on a kaiser roll changed my life.
• Alleyway Ice Cream in Saugerties for really interesting ice cream flavors. Alleyway may honestly be the best ice cream I’ve ever had. They have flavors like ube Heath bar crunch, Thai tea cookies ‘n’ cream, and sweet corn. You can tell each ingredient is homemade with love.
• Grazin’ Diner in Hudson for farm-to-table burgers. You know it’s gonna be a good burger when every single ingredient’s origin is thoughtfully described on the menu.
• Wayside Cider in Andes and Brunette Wine Bar in Kingston are super cute spots to drink, depending on if you want cider or wine, respectively.
• Kingston Bread + Bar in Kingston for your carb fix. If I were a local, I’d be picking up my pastries from here every week. They have a lot of typical Jewish pastries, as well as things like cardamom buns and baklava rolls.
• Lis Bar in Kingston for wood-fire grilled meats in a cozy atmosphere and movie nights on Fridays.
• Supernatural Coffee in Hudson for coffee and pastries. Perfect for a quick early morning breakfast if you need to rush off to a hike.

Hikes

Kaaterskill Falls might be my favorite hike in this region. There are two trails: an upper trail leading to gorgeous valley views, and a lower trail going down to a double-drop waterfall. It’s an easy hike and gets crowded early, so go before 10am to find parking. The lower trail has a staircase that gets slippery from the waterfalls, so just be careful.

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Anthony and I tried to hike Gertrude’s Nose at Minnewaska State Park Preserve, but it happened to be closed that weekend, so we ended up on another trail called Millbrook Mountain. While it wasn’t the challenging, epic hike I was hoping for, the views across Lake Minnewaska are absolutely stunning, especially in the fall. Once again, get there early for parking.

While Breakneck Ridge isn’t technically in this region, it’s on your way back to the city and is still my favorite in the entire state. Quick, challenging, and rewarding, Breakneck Ridge will always hold a special place in my heart because it was the first hike I did in New York. There’s a vertical scramble that may seem intimidating but is actually quite doable if you’re moderately fit and flexible. Stop by the charming village of Cold Spring after. (While you’re here, of course check out Dia:Beacon and Storm King Art Center. I’m not gonna even bother writing about those — if you haven’t visited these obligatory art institutions yet, you’re doing New York wrong.)

Random Things to Do in Kingston (where I spent the most time)

If you’re into American history, Kingston is a fascinating place to visit. It’s pretty large compared to the other towns in this region. Kingston was New York’s first capital and was burned by the British during the Revolutionary War. You can see some of the original pre-Revolutionary buildings, as well as beautiful Victorian homes in the Stockade District.

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Also in Kingston is a 2.3-mile railroad trail that follows a creek. It’s a nice way to walk through town, as it connects the waterfront to midtown.

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Anthony’s former coworker opened up a bookstore bar called Rough Draft that has become the hottest place to hang out in Kingston. When you visit, you’ll see why. Housed in one of the historic buildings in the Stockade District, this cozy bookstore has lots of space for reading, grabbing a coffee or cider, and attending one of the many events they host.

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