3 Days at Windham Mountain in the Catskills
We spent 3 days in the Catskills
In upstate New York to ski and relax at Windham Mountain. It was beautiful, barely 2.5 hours away and just what we needed for a little winter adventure. I only learned to ski last winter but fell in love with it and everything that comes along for the ride when you’re on a ski vacation. I also know very little about upstate New York and am still learning the ropes on ski trip life so I put together a guide based on our trip for those who are interested to book their own adventure.
Last year when we went to Breckenridge I invested in great ski gear to stay warm and look cute at the same time. I love Half Days because it’s super comfortable and makes me look the part while I am learning. I also invested in a cute belt bag which is probably one of the best things I’ve ever bought to be honest. It carries the essentials, looks great, and keeps me hands free. Aside from my phone and wallet, my #1 essential is this hand/lip balm from Waxlene as it keeps me moisturized and not drying out from the cold air.
The first thing you need to know about booking skiing upstate is to check the availability of ski school, lessons, and lift tickets. Things can get full fast so before you even look at hotels/rentals check the mountain’s availability. We don’t always plan well in advance so we’ve been SOL a few times. Lincoln and just learned to ski last year so I wanted us to both take lessons again this year. Windham Mountain is private so it’s less crowded but also more expensive than other ski options in the area. I will say it was VERY organized and civilized when it came to parking, etc. Everything was smooth and there were all kinds of people around to help if you have questions.
We rented skis from the mountain and as long as you’re there before 9, the lines are short and there’s little crowds. If your kid is doing ski school, the school sets them up with skis so it’s even easier! Ross and I bought helmets and goggles for this year and I invested in ski boots from Sure Foot as my arches are very high so it was super helpful to have perfectly fit boots. They were expensive but worth it!
We went up on a Thursday late afternoon around 3pm. We had to stop a few times on our way out of NYC but once we got going it took us about 2.5 hours to get to Windham. We stayed at the Wylde Hotel which was not even 5 minutes from the base of Windham Mountain. After checking in we ate at the hotel’s restaurant, Babbler’s which was delicious and had something for everyone. We finished our first night there with s’mores at the fire pit.
The Wylde was super cute and very family friendly yet also had a very cool low key vibe. Not to mention had a great nightly rate. They have a main house where reception is, the restaurant/bakery, a cozy lobby with a fireplace and hot toddy station. There are a number of big “houses” on the property which is where all the rooms are. We were across the street which was easy enough.
Friday morning we got up early and had breakfast/coffee at the hotel Bakery. They had lots of pastries plus eggs and gluten free options. I opted for coffee out of a mug because it tastes better and paper cups are lined with BPA/are bad for the environment.
For our first day skiing on Friday we put Lincoln in ski school all day from 9-3. I took a 2 hour lesson and finished the morning off skiing by myself for a bit. While I worked on the green runs, my husband skied solo on more challenging runs. We then met up, checked out the dining options and had lunch.
Because Windham Mountain is partially private, certain restaurants are not available. We ate at Seasons, the Lebanese style restaurant upstairs in the lodge. I had a salad with chicken shawarma and it hit the spot perfectly.
After skiing we stopped by Clutch and Throttle for coffee and a snack for Lincoln. It was so cute and the coffee was so good. They also had markers and coloring books for us to take a break and recharge.
We finished the night off playing games in the hotel’s game room then hit up a local book shop, Briar’s and Brambles. We then met up with friends from Lincoln’s school and ate at Union and Post which was very good and super family friendly as they had a little play area for the kids to burn off some steam during dinner.
Saturday we started the same with breakfast/coffee at Babbler’s at the hotel. We skipped the lessons and skied as a family in the morning, had lunch again at Season’s and finished off the day with a few more green runs. It was getting icy so we decided to call it a day.
We then hit up Clutch and Throttle for another afternoon coffee break.
We headed back to the hotel for a little r&r before dinner. Lincoln and I hit up the game room while my husband rested.
My favorite part about ski vacations is that for now the last two times we have gone our son watched no TV. We don’t do screens like ipads, video games, etc. and because a ski trip is so active there’s little downtime and when you are finished, you’re so tired you go to bed early and start over the next day. The Wylde Hotel did have a downstairs game room with every billiard you could imagine plus Pac-Man which was super fun and gave our son a little fix without sitting down to watch TV.
I then hit up the barrel sauna (you reserve yourself a private spot) to warm up and sweat it all out. We then freshened up and shopped around Windham while we waited for our table at Millrock to be ready. The one thing I WISH we could have done would have been able to see the Magic Show, it was sold out unfortunately but I heard it was very good! If you’re heading up, I recommend you book ticket.
Sunday we had a slow morning but eventually made it for coffee and breakfast at the hotel one more time. We then went for a rather icy walk on the 1.5 mile trail, “Windham Path”. It was fun and a great way to get some fresh air and move the soreness out of our bodies from skiing.
Our last big activity was the Windham Mountain Tubing Park (be sure to book in advance) where there were multiple runs happening at once plus a magic carpet to bring us up to the top of the hill. I think we did at least 15 rides and it was SO fun.
We finished off our trip upstate with lunch at The Chicken Run which was a very low key yet delicious lunch spot. It didn’t take long and was the fuel we needed to get us back home to NYC.
I hope you find this helpful in planning your own trip up to Windham Mountain! I find navigating ski mountains, accomodations, etc to be kind of confusing so I tried to break this down as clearly as I could. Maybe it’s just because I’m still learning the ropes (or slopes lol) of the whole lifestyle but it always seems a little elusive to me. If you try any of my suggestions, be sure to tag me on Instagram @AshleyPattenPilates and/or comment below!
xx, Ashley