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Solo Trip to the Catskills – A weekend escape to the mountains for a bit of R&R

SPONSORED — My solo trip to the Catskills was sponsored by Expedia. Visit or download the app to book your own solo trip today!

Solo travel hiking in the catskills

Ever since my first solo trip around the world, I’ve been hooked. There’s something special about visiting a new place for the first time—alone and unencumbered with travel companions or preconceived ideas.

I’ve lived in New York City for just over a year now, and like any of my other homes, I’ve made a point to discover what I can, when I can. As a recently legal resident, with a New York driver’s license even, I figured it was about time I took some time to explore New York state outside of the bubble that is “the city.”


Choosing where to go for a digital detox

After a busy month of NYC pride events, I knew I needed a weekend in July to unwind. Just a few days to myself to catch up on some journal-writing, and to clear my head. My first instinct was to book a weekend to a nearby beach, but after some thought, I figured it was time I went a little bit north and up into the mountains.

I’ve known of the Catskills for years, but in all my visits to New York City, I never ventured further than Brooklyn.

My connection to the Catskills requires a little bit of history. For a time in college, I studied art history, specifically Romanticism. (For anyone that’s been following me for years, that’s part of my connection to Germany and why I probably fell so hard for German culture—but that’s another story.)

Here’s the thing: Romanticism has a lot of close ties to Transcendentalism and the Hudson River School—New England philosophies and movements which were the foundation for a lot of my favorite writers’ and artists’ works. And a lot of their inspiration came directly from the landscapes of the Catskill mountains and the Hudson valley.

Having never been to the Catskills, from years of studying art history, I thought I had a pretty clear guess of what it would be like. Sweeping green valleys, swerving rivers, and little hillside cottages along farms. Maybe some sweet ice cream shacks and roadside vegetables for sale. It sounded like just what I needed for a quiet weekend away from NYC nightlife.

Booking a trip to the Catskills using the Expedia app

So, naturally: I was curious what this part of New York was like. Using the Expedia app, I searched for hotels and packages that would help get me to the Catskill region. It’s only a few hours drive north of NYC, but without a car, it’s a challenge to reach.

The Expedia app can automatically recommend itinerary options to save you money!

Thankfully, in the Expedia app, you can book parts of your trip separately, and any applicable discounts will come through as you book. I knew I needed a rental car but wasn’t yet sure which town in the Catskills I was going to stay in, so I booked that first.

A few days later, when it was finally time to book my hotel (a motel, truthfully), a “package deal” discount was automatically applied in the app. With a motel booking and a rental car to pick up near my apartment in Brooklyn, I was ready to go!

Solo Travel in the Catskill Mountains

Probably my biggest challenge of the weekend was, predictably, getting out of NYC traffic on a Friday afternoon. Thankfully the traffic really only added an hour onto my journey, and I was up in the region by nightfall and checked into my motel relatively easily.

The crickets were chirping when I arrived. Dark roads, a warm summer breeze, and a flickering neon sign welcomed to my accommodation. As soon as I pulled up, I was immediately reminded of my childhood trips with my family when we’d stay in motels or KOA campgrounds.

My room was modest—and nothing special. Wood-paneled walls and a porch out front with two lawn chairs. Yep, this will do, I thought. The perfect weekend escape.

It was too dark to see much of anything, just some stars in the sky above, but next door to my motel, the only other building I’d seen for a mile was—you guessed it: a craft brewery.

Perfect!, I thought. In my flip-flops and a hoodie, I walked over and sat at a table, ordered a burger and a beer, and watched the people around me. The bar was crowded with a group of guys, the type that work with their hands. Fox News was playing on the TV overhead, but I quickly tuned out the world.

This weekend was going to be a chance to tune out the world, to go back to nature, to simply rest.

The next morning, I took my books and a reusable water bottle and headed to the woods. A stop, first, in a local deli & grocer for a breakfast quiche, and then I was on my way to the famous Kaaterskill waterfall.

Sometimes you just need a walk in the woods

My solo weekend in the Catskills was just the kind of weekend I needed to inspire and motivate me. I managed to spend a lot of my time alone in my head, reflecting on my relatively crazy summer and brainstorming bigger ideas and projects I still want to do this year.

I spent a few hours in and around the Kaaterskill waterfall with my books (I packed three). But when a brief rain shower came in, I made me way to the nearest town. I found a cute restaurant with outdoor picnic tables and opted for a brownie ice cream sundae for lunch, because that’s the proper way to #solotravel!

ice cream sundae

By the late afternoon, I was back at my motel to enjoy the pool in the sun, and more time with my book. Some other guests were there, drinking beers and getting some sun while blasting Queen on a stereo.

swimming pool legs

It was all really pleasant and simple. The opposite of my weekends in NYC where I’m running between activities and friend groups. For my big Saturday night out in the Catskills, I actually drove 20 minutes to the town of Hudson.

Along the Hudson River, the town is famously gay-friendly, so I met up with some friends there for dinner and drinks. A leisurely night out in another quiet town.

Waking up Sunday for my drive back to NYC, I felt rejuvenated. Refreshed from a few days of that fresh mountain air, the lush greenery, the open skies. Sometimes you just need a walk in the woods to set you back on the right path.

Solo Travel in the Catskills with Expedia
expedia logo

My solo trip to the Catskills was sponsored and supported by Expedia. Expedia has a pretty good grasp on how and why we like to travel, and knows that modern millennial travelers like myself enjoy these kinds of occasional digital detoxes. Solo travel gives you the chance to get out and explore on your own, to learn and to think, and to experience new things.

This summer, Expedia released their first Solo Travel Report which includes destination recommendations, helpful planning tips, and cool new insights on how we can navigate solo trips.