36 Hours in The Catskills: A Quick Fall Getaway

Must-read tips for planning a quick fall getaway in Upstate New York’s Catskills Mountains.  

I remember my first time.

The time I said, screw it, big city – I’m taking a nature break.

I didn’t really know where I was going or what I was getting myself into. I had a bag of snacks, a bottle of water and a semi-functional car GPS leading me to one dot on the map:

The Catskills Mountains.

While I may be biased given my absolute adoration for all things Catskills (I visit at least once per month), this region is great for any New Yorkers or East Coasters seeking a quick weekend getaway. Most mountain hikes take no more than half a day, and it’s filled with wineries, breweries and quaint cultural highlights for those post-hike celebrations.

Oh, and did I mention fall foliage? Because it’s pretty epic up in these parts.

Accommodations

The Catskills have plenty of accommodation options. You can book cabins through VRBO and Airbnb, stay at hotels like the Hudson House River Inn, or even rent tents through the new rent-a-tent service Tentrr. And of course, there are plenty of campgrounds for those who’d prefer to pitch their own tent.

In terms of places to stay, I’d recommend the area around Hunter, Windham or Woodstock, but of course – anywhere in the Catskills will do!

Getting there

If you don’t have a car, rent one or get a Zipcar. While there may be ways around this, trying to get to everywhere without a car is a hassle, so trust me when I say it’s worth every penny.

Duration

While you can go for the full weekend or longer, I’d recommend not leaving on Friday night after work. Getting out of the city Friday evening is straight miz, and you’ll wind up driving through pitch black forests trying to find an unmarked cabin or – even tougher – tent.

Instead, if you’re planning a quick weekend getaway, I’d suggest beating the traffic and hitting the road early Saturday. It’s only about two or so hours, so if you get out by sunrise, you’ll have a full Catskills day ahead.

Here’s a brief itinerary of my favorite spots to help you plan out your fall Catskills getaway.

36 Hours in the Catskills – A Sample Itinerary

Friday night

While you may not be leaving until tomorrow, you should pack up ahead of time so you can roll out of bed and go. Bring lunches for a post-hike picnic, waters for your hike and snacks for your time on the road, because no road trip is complete without some unnecessary but delicious junk food. (Go for the Goldfish!!)

Saturday morning

I wasn’t lying when I said it’d be an early morning, so get that butt out of bed – it’s time for adventure! For the sake of your fellow passengers, please grab coffee on your way out the door, because nothing’s worth than starting a road trip on the wrong side of the bed.

Aim to leave by 8 a.m., that way you can fit in a hike before check-in. Given time limitations, it’s probably best to stick to a shorter hike so you can embrace nature while still allowing time for other Catskills activities.

For new hikers, I’d recommend Kaaterskill Falls, a quick, one-hour hike that looks like a painting during peak fall foliage weeks. For more seasoned hikers, I’d definitely hit up Slide Mountain. It’s about four hours roundtrip and offers sweeping views across the region.

 

Saturday afternoon

Finished your hike? Now it’s time to feast! Stop at a campground or really any pretty spot along the road and dig in. Enjoy the peace, and listen to the absolute silence – it’s one of my favorite things about the Catskills.

Once you’ve refueled, plug “Bethel, NY” into your GPS – you’re heading to the real site of Woodstock! While there’s a town in the Catskills called Woodstock (which I’ll get to later), the iconic music festival actually took place on a farm out in Bethel. There’s a full museum or you can walk the grounds, but if you’re short on time, the Woodstock monument with views of the stage and fields will do.

Cap off a good day with a stop at the Catskills Brewery, an unassuming taproom in Livingston Manor. If you’ve decided to bring your pup (as I typically do), you’re in luck – the Catskills Brewery is dog friendly!

Note: At some point you’ll have to check into your accommodations – build this in somewhere above…

Saturday evening

If you’re up to it, you can grab dinner at a Catskills restaurant like Hammos Brewpub and Lodge, or you can take my preferred route and get groceries (don’t forget the booze!) and grill out at home. This lets you eat outside while watching the sun go down and drinking your own good beer.

Oh, and in case you forgot – look up! Once dusk hits, the stars put on an incredible constellation show. Throw on a sweatshirt, brave the chilly air and cherish these twinkling stars as long as you can stay awake.

Sunday morning

Hope you weren’t planning on catching much shut eye this weekend, because you absolutely need to wake up before sunrise. Say wha?!

No, seriously. There’s nothing better than waking up to coffee and a sunrise in a sleepy little mountain setting. Once the sun is up and you’ve taken it all in, cook up a quick breakfast, grab another cup of coffee (assuming, that is, you need two cups of coffee by 9 a.m. like yours truly) and enjoy that mountain view once more.

After that, it’s time to (sadly) pack up and head out, but don’t worry – there’s still adventure to be had on your way back home!

Sunday afternoon

Drive back to NYC by way of Woodstock, New York, to visit Sunfrost Farms for some no-frills pumpkin picking (no patch, all pre-picked) and fresh, homemade food. Take a quick stroll around Woodstock and check out the cute little shops and town square before heading onto stop number two: Benmarl Winery!

The Hudson Valley region has some impeccable vineyards, and Benmarl is by far one of my favorite – especially during fall. It’s set on a hilltop with views out over the Hudson River, and they have tastings and seating inside and outside so you can enjoy the epic scenery.

Last stop on your journey home will give you all the fall feels – Sleepy Hollow, New York. Yes, the Sleepy Hollow, AKA Ichibod Crane and the Headless Horseman!

Stop by the Sleepy Hollow Cemetery to view the grave sites of Washington Irving, Andrew Carnegie, Walter Chrysler and Samuel Gompers. Take a stroll around the beautiful Phillipsburg Manor (we didn’t actually go inside due to limited time), and of course, check out the Headless Horseman Bridge. (Clip clop, clip clop, clip – you get the picture.)

Sunday evening

I hate to break it to you: It’s time to head home. Crank up that playlist, enjoy your last few minutes of serenity and get started on planning your next epic weekend getaway, because as John Muir (never) said:

The Catskills are calling, and I must go.

Side note: Even if you’re not from the New York area, you should definitely check out the Catskills once in your life! They’re beautiful (as you can tell), and easy to tack on to an East Coast trip.

Have specific Catskills questions for me? Ask away & I’ll do my best to answer!