Catskills

Travel

A week in the mountains of Upstate New York

I needed a vacation in January 2020, even more in March, and by the time September came around I was going full stir crazy in my house. With quarantine, lockdowns, and travel restrictions in place, we had to get creative on where we could go for a much needed escape from the city (Chicago). Looking for something drivable, scenic, and remote, we settled on the Catskills for a fall getaway.

This by no means covers all of the amazing places to stay and visit, but here’s a guide to our week in the Catskill Mountains Fall 2020.

Where to Stay:

Bank House Airbnb

Our first stay was the old Bank House located in Stoneridge. I can’t say enough great things about this house, and pictures just don’t do it justice. From vintage wide planked floors, to stone facades, to copper plumbing, this architectural gem is an Upstate NY dream. Perfect for a group or a couple, the house is equipped with 3 bedrooms, 3 baths, a full kitchen, fireplace, screened-in porch, large back yard and more.

Images from Airbnb listing

Airy Catskills Barn

Next up, the Airy Catskills House located in Hortonville. This quaint river house had everything we needed for a cozy and more budget friendly getaway. The best feature of this property was the pond located right off the back deck. You could find us here having a morning coffee, afternoon hammock nap, or a night cap after dinner. This airbnb was super close to Livingston Manor, Roscoe NY, and Bethel NY.

Images from Airbnb listing

The Arnold House

Last up, the Arnold house. On our last night at the Airy Catskills we decided we needed one more night in New York, so we booked a room at the Arnold House. Owned by Foster Supply Hospitality, The Arnold House is a perfect retreat built on 80 acres of land and man-made trails in Livingston Manor. Because of Covid, we couldn’t enjoy the indoor living room, but on a “normal” day this would be a great place for a game of chess and a cup of coffee in front of the midcentury fireplace. Behind the Main Building is the Garden House, open to fresh air, this space is ideal for picnics and plant lovers. For dinner, we grabbed food and whiskey sours from their tavern and dined in front of the huge firepit just outside the Garden House. Because it was a special weekend, we opted for a giftbasket which included champagne and apothecary goodies from their spa. Finally, before our drive home, we ventured out into a few of the property’s trails.

Where to Eat/Drink:

1. Garden Cafe- Woodstock

The Garden Cafe is an herbivore haven, serving up healthy     vegan comfort food, specialty juices and more. You’ll likely over order here because there are way too many options to choose from… in the best way.

2. Kaatskellar- Livingston Manor

The Kaatskellar is a must visit if you’re in Livingston Manor. This woodfire pizza restaurant is decked out with string lights, craft cocktails, and cozy firepit vibes. To top it off, there’s a vintage camper parked out front that sells the most amazing oatmilk gelato.

3. Main Street Farm- Livingston Manor

When I say I’m still daydreaming about this place, I’m not lying. I think about my lunch from here at least once a week. Main Street Farm is half restaurant half marketplace, selling organic/artisanal/local products. On our visit, I swiped a candle from the shop and the Willowemoc sandwich w/ a matcha latte from the cafe.

4. Prohibition Distillery- Roscoe, NY

We did our fair share of drinking on the trip too. A favorite spot was Prohibition Distillery, known for their gin, whiskey, and vodka. You can check out the tasting room, makeshift patio, or take a bottle to go. If you buy the gin, I recommend getting the Morris Kitchen cocktail mixer for a refreshing pairing.

5. Phoenicia Diner- Phoenicia

This diner is straight out of a scene from Twin Peaks, surrounded by mountains on all sides. We grabbed a quick lunch here and enjoyed the mountainous view from our car before our railcar adventure (just down the street from here). Put on some plaid and Eastland boots and check out this diner for the ultimate Catskills lumberjack aesthetic!

What to Do:

1. Upward Brewing Company- Livingston Manor

Take a hike up beer mountain or a yoga class in the grass… after reward yourself with some beer from Upward Brewing. Non-covid, the inside of Upward would be the ultimate Catskill lodge to settle in by the fire post-ski and drink a brewski. For now, guests can pull up a chair to the firepit, pitch a blanket, or set up camp around the pond for drinks and a view.  

2. Thrift!

You didn’t think an interior designer could go to Upstate New York and not thrift did you?! For cute vintage stores head to the main strip of Woodstock or Front St. in Kingston. The best way to find hidden gems is to ask the locals where their favorite places are. Most likely they’ll tell you to check out random old barns and parking lot sales on the weekends. Check local listings for estate sales and yard sales going on in the area too.

3. Rail Explorers- Phoenicia

Admittedly, I found this adventure on TikTok and decided we HAD to do it. I’ll tell you we weren’t disappointed. Located in Phoenicia, rail explorers is a pedal-powered vehicle that runs on an old railroad track. This specific path runs along the Esopus Creek into the woods of the Catskills. There’s a small break halfway, where you’re encouraged to picnic and bring beer/wine. Even dogs are welcome!

Well, that was a paired down version of our week in the Catskills, but I covered almost all of our favorite spots. The Catskills are truly the perfect city getaway, whether in the fall when the leaves are changing, the winter months to cozy up by fireplaces, or the summer to enjoy hiking and flea markets. Thanks for following along!