A Weekend in the Catskill Mountains of New York

Over New Year from 2021 to 2022, Teddy and I decided to take a weekend road trip to New York. Both he and I had never visited the Catskills before more then driving through them and wanted to do some exploring. We didn’t really make a plan for this trip other than to book an Airbnb for two nights. We wrote down some ideas of towns we could visit, parks to go hiking, and places to eat but didn’t have a plan of what we would do each day while there. This was more of a “let’s just make plans as we go type of trip”.

We started our 4 hour trip north by stopping in Clinton, NJ. This was an unplanned detour. We saw a sign for the historic down and I looked it up and realized I’d been here quite a few times as a kid with my uncle around Christmas. Teddy and I got off at the exit and explored the downtown for just under an hour. We got coffee at The Stone Bean, walked across the bridge to see the mill up close, and walked into a few other shops downtown. The town itself was adorable, and decorated beautifully for the Christmas holiday. This would be a great down to visit again.

After leaving Clinton, we continued our drive north toward Woodstock. Yes, that Woodstock. the one often associated with the Woodstock Festival. Interestingly enough, the Woodstock Festival was actually held about 60 miles away in Bethel at a dairy farm.

We got into town and it was packed. It was a holiday weekend and we were there around late lunch. We had planned to grab lunch in town but many of the sit down restaurants had lines outside just to eat. We walked around trying to find something quick and easy and came upon a pizza shop. The sign outside looked appealing, so we went in. This is when it got weird.

We entered and saw the pizza oven and the other normal items you’d see behind a counter for a pizza shop straight ahead. To the left was a variety of items you’d find in a convenience store. From various medications to baby diapers to laundry supplies and a panini press, they had it on shelving on the left in the middle of the seating area. For tables, they had 5 or so tables with chairs or booths and then a sofa sitting in the middle of the shop. A sofa could work inside a pizza shop if done well, but this looked like it came from a local living room from the 1980s. We had already begun to walk up to the counter to order as we were taking this all in and were very hungry at this point. We considered leaving but the man behind the counter already started loudly pressuring us – “What do you want?” before we even got to look at a menu. We ordered the simplest thing we could, a pizza, and found one of the few seats inside to sit. While we were making our way to our seats, a group behind us also ordered a pizza, and the man taking the order started to look visibly stressed and annoyed and told them that the pizza would be a long time to wait. They said that was fine and they’d wait. The other individual working told the one taking orders that he’s overwhelmed and can’t take any more pizza orders. There were a total of about 8 customers in the store at that point including us, one group who was already eating their food. As we sat, we ended up beside a man on the couch behind us. Had had no food or drinks but was sitting taking some type of Rosetta Stone language course on his phone with the volume the entire way up. Teddy and I each sat silently looking at each other trying to process what was happening. During the 20 minutes or so until our pizza came in, additional people tried to order pizzas and were told they weren’t taking pizza orders. There was also an instance of someone coming through the back door to deliver food to the two employees where they began to discuss a party that evening and who was bringing what alcohol and food to it.

All in all, it was one of the weirdest experiences I’ve had in a food establishment to date. What made it even more odd was that the pizza was actually delicious. We truly had incredibly low expectations after all that was going on inside, and were so surprised that the pizza was so good. When we finished up and left, we saw a sign on the front door that said “Business Partner Wanted” and mentioned something about must have experience in business and sales. That probably should have been a red flag before we even walked in. We were curious if this was just a bad day for the employees or just the vibe of the place, but we read some reviews online after and saw that our experience was unfortunately not unique. We ultimately hope that they found the business partner they were looking for and were able to turn the shop around. But for us, this was a great reminder of why we usually check Yelp reviews before we go anywhere. While we’re interested in hole in the wall places, when there’s poor service, it really sets the tone for a negative experience.

Woodstock as a whole was a unique experience. It is not for everyone. We decided that that town was a once and done for us after checking out a few other cafes, shops, and walking around downtown. After having some conversations with locals in other Catskill towns over the next two days, we realized just how different some of these mountain towns are and that each one attracts people with very different interests. To summarize our experience in Woodstock in one word, we’d describe it as eclectic. We were ready to but also a little nervous to head to the next town where we’d be staying as we were really unsure what to expect next.

Roscoe was our next destination. It is about 90 minutes west of Woodstock. To get there, you drive through beautiful mountains and wilderness. Like I said, we were a little nervous and unsure what to expect in this town and our accommodations. Wow, were we pleasantly surprised. We truly couldn’t have asked for a better place to stay during our visit.

We stayed at the Red Rose Hotel & Tavern right outside of Roscoe. I initially found it on Airbnb while checking out places to stay in the area, and loved the decor of this place. If I had a little mountain cabin to decorate, this is exactly what it would be. It was cozy and comfortable with its mix of various antiques and nods to the area.

The Red Rose Motel & Tavern is a historic motel built that was built in 1938. The decor has pieces of taxidermy, traveling pennants, outdoor adventures, and other cozy antiques. I had a hard time choosing which room we wanted online, but we picked the one with the desk and sitting area. We were tired from the driving during the day, so went over to the lounge and eating area inside the inn for dinner. While they have a simple menu, there were great options and we picked burgers and bottled sodas for dinner. There were various guests coming in and out that evening since it was New Years Eve and since the dining area is also the common area, we got to talk to a few people who have been coming to the area for years. We learned about hunting in the area, got tips for local restaurants to try, and what towns we may like to visit during our trip. It was such a unique opportunity to talk to so many varying people by the fireplace of the inn.

We somehow managed to stay up until midnight to ring in the new year. There were various local beers as well as champagne and wine set out for guests in the main area where you jotted your name down so they could charge you later. We each tried a local beer before deciding to call it a night and get ready for our adventures the next day.

The next morning we got up and grabbed some coffee in the dining area before driving into Livingtson Manor for breakfast. We stopped at The Walk In for biscuit breakfast sandwiches and then continued our drive east. We drove about an hour until we got to Minnewaska State Park Preserve. We did the shorter hike down to the Awosting Falls in the fog and then hiked part of the path around Lake Minnewaska. There are a few other waterfalls in the park as well as a ton more hiking trails.

After our hike we drove into New Paltz for lunch. The town reminded me a bit of New Hope in eastern PA if you’ve ever visited. It was artsy with some interesting shops but still approachable. Not as eclectic as Woodstock in our opinion. Some places in town either weren’t open yet or had a wait, so we ended walked around town and found McGillicuddy’s. There wasn’t a wait and we really enjoyed the food. It’s traditional American bar food but it hit the spot. We then headed back toward our Airbnb and relaxed before dinner. We decided to go to one of the spots recommended by someone who visits town frequently called the Riverside Cafe. The entrance isn’t as inviting as you’d hope but it’s got a great view by the river and the food was good. I especially liked the fig and prosciutto pizza with arugula that I ordered. We were exhausted from a day of driving and exploring so we headed back to the Airbnb to get some sleep.

The next morning we grabbed breakfast and I worked on some blogs in the dining area before hitting the road. We both said we could have stayed at the Red Rose Motel & Tavern a few more days and definitely plan to come back. The owners and employees were so welcoming and so were the guests. It was such a unique experience and we loved it.

While we had some unique experience on this trip, Teddy and I both loved this trip together. We laughed so much, got to explore new areas, and overall just had a great time even though we went into it with no real plans. I’d definitely recommend a weekend trip here if you’re looking to explore some small towns and want to spend time outdoors and would highly encourage you to check out the Red Rose Hotel & Tavern as your homebase for the trip.

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