A Weekend in the Catskills, NY
- Kelly Risk
- Sep 7
- 6 min read
Here is my weekend itinerary in the Catskills, NY! We focused our trip on the Eastern Catskills with our base being Hunter, NY. The Eastern Catskills are closer to both Albany and New York City and are therefore busier with tourists. My husband and I planned our trip very last minute (a week in advance) over Labor Day weekend; while there were definitely tourists, it was never overwhelming. I have heard during the fall it can get quite busy, though. The weather over Labor Day was stunning: high 60s/low 70s during the day and 50s at night. It was refreshing after a hot summer! We only spent 2 nights, but easily could have spent longer.
The Catskill mountain range is known for its hiking in the summer and skiing in the winter. It served as inspiration for a group of landscape painters who made up the 19th century art movement called the Hudson River school, of which you can visit the historic site of the Thomas Cole Art School. It is also where Washington Irving's famous short story Rip Van Winkle took place! And you will see many places named after ole Rip. The region was settled and named by the Dutch; the Dutch suffix -kill means a creak or stream. The original way to spell the Catskills is Kaatskills! My husband and I really enjoyed the outdoors paired with the "bougie-ness" that comes from an area catering to the NYC crowd: all the food, lodgings, and amenities were fantastic. There are a lot of nicer farm-to-table restaurants for a fancier night out, but we sadly did not have the time to try any. Also for any fans of Severance, the Phoenicia diner is nearby and was featured in the show.
My husband and I absolutely loved our time in the Catskills and cannot wait to come back and explore more!
Day 1: Arrive and enjoy hotel
Driving to our Catskills base of Hunter, NY from the DC-area takes around 5-5.5 hours, which was still surprisingly the case on a holiday weekend (Labor Day). We planned this trip only a week in advance but were surprised to find that the beautiful Hunter Lodge, a Bluebird by Lark property, still had decently-priced rooms available. We stayed in one of their last rooms, which actually ended up being a 4-queen bed bunk room called "The Friendzone" (my husband loved this, lol). The room was super comfortable and would honestly be great for families with kids! The property has an attached tavern and the food was quite good the one time we ate there. There is a limited breakfast available that we did not take advantage of in addition a beautiful communal gathering space with books and games, an outdoor bonfire and lawn games, and a little game room with some arcade games.
This area has a lot of great hotels to consider! I also really had my eye on Eastwind Hotel in Windham (13 minutes away) and the hotel across the street from ours (Scribner's Lodge) also looked very nice.
Day 2: Hike and explore
After a leisurely morning, we opted to start our day at Hunter's absolutely adorable Fellow Mountain Café. Everything we had here from baked goods to coffee was delicious, particularly the oatmeal almond cookie. A lot of gluten and dairy free options as well!
We then headed to our hike for the day: Inspiration Point to Kaaterskill Falls Loop. The portion of this trail to the falls is the most popular hike in the area and is quite easily accessible for most ages. Because of this, it was quite crowded and we could not park in the Scutt Road parking area as AllTrails suggests. Instead, we continued down the road to the North South Lake State Park entrance--which cost $10 per vehicle--and parked at the South Lake parking area. This maybe added about .5 miles overall as we hiked the North Lake South Lake Trail to meet up with the Kaaterskill Falls trail to get to the main loop. We took the trail counter-clockwise, against AllTrails' suggestion, because it was recommended by previous hikers for having less uphill time and would highly suggest this. This meant we headed straight towards the falls with all the crowds. This part of the trail is wide and despite the amount of people, it never felt overly crowded. The first side trail to see the falls takes you to a viewing platform at the top that had lovely views. The falls this time of year (late August, early September) did not have a lot of water because of a drier summer and were not as spectacular as they can be. Because of this, we skipped the second side trail to go closer to the falls. Once we continued up the trail (towards Layman's Monument), the crowds totally disappeared. We loved the trail and views! In the last stretch, my husband rolled his ankle jumping down from a rock--it wasn't bad, but we opted to skip more hiking this trip.
After our hike, we grabbed a late lunch in the super cute town of Tannersville at The Pantry on Main (we drove through this town on the way from Hunter to the hike). The food here was delicious! We also strolled through a lot of the shops. Because of my husband's ankle, we opted to take a pretty drive to Saugerties and grabbed some ice cream at Sawyer Ice Cream Company before wandering their cute downtown area a bit. They had dog statues up everywhere that were fun! We spent of a lot of time perusing the Inquiring Minds Bookstore.
After driving back to the Hunter Lodge, it was starting to get dark and our hotel's bonfire had been lit. We had such a fun time sitting around the fire talking and sharing stories with several of the guests! The hotel offers s'more kits for purchase (they're huge!), but after our s'mores ice cream earlier that day we passed. After wrapping up at the bonfire, we enjoyed some late appetizers from the tavern (the charcuterie board was so good) and spent the rest of the night reading our new books.
Day 3: Enjoy more of the scenery before departure
After checking out from our hotel, our morning started much the same as the previous day's with a visit to Fellow Mountain Café. We enjoyed our breakfast and coffee on a blanket in the lawn area in front of the café which was a great spot to dog-watch and read a book in the sunshine. We tried not to fill up too much because we wanted to try more of the local bakeries, for instance Shandaken Bake in Tannersville was highly recommended. But after Fellow's, our stomachs could only handle one more stop and we chose Fred's Coffee and Donuts. Their donuts are made fresh and were very good!
In search of rolled ankle-friendly activities, we went to the Hunter Scenic Skyride. This activity has surprisingly low stars on Google maps, but we loved it! We were able to walk right up and buy tickets ($27/person) and get right on the ski lift without waiting in a single line or having to share our lift with anyone else. The reviews seem to suggest this is not the case in prime leaf peeping season. The ride up the mountain was about 15 minutes and was gorgeous. Once at the top, there is a nice viewing platform for photos and we were able to wander around the top and soak in the views. The restaurant at the top that is open during ski season was not open when we were up there. And of course the ride back down was just as beautiful!
We then begrudgingly had to leave the Catskills. For a return trip, Rail Explorers looked really fun. On the drive back south we did stop in Tarrytown/Sleepy Hollow, NY. This area, right along the Hudson river, is also quite pretty and home to a historic estate once used by the Rockefellers, but this was closed by the time we got to the area. Instead, we just walked around Tarrytown and got some food for fuel the rest of our drive back.
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