One of the great things about living in NYC is that there are so many interesting places you can escape to for the weekend. Recently, my husband and I took a weekend road trip to the Catskill Mountains, an area in upstate New York that is now booming with chic, boutique hotels, hipster shops, and farm to table restaurants.

what I love about the Catskills is that it’s an ideal destination to visit year-round. No matter which season you go, there are plenty of things to see and do, from skiing and snowshoeing in the wintertime to hiking and swimming during the summer.

There are so many towns to visit that it’s impossible to fit them all in one weekend. For this overnight getaway, we chose to explore Woodstock, Phoenicia, Roxbury, and Saugerties. Below is our exact itinerary of what we did, where we ate, and how we fit in plenty of exploring, in the Catskill Mountains.

Related: Safe Places to Stay in The Catskills During COVID-19

Related: Weekend Itinerary for Livingston Manor, in the Catskills

Road trip to the Catskills: Saturday

Our First Stop: A Hike in the Catskill Mountains

 A friend of ours who has a place in Woodstock, recommended we try the trail at Overlook Mountain, just outside of the town of Woodstock. (Don’t you find the best travel tips always come from locals?!) Since the majority of the hike actually entails walking up an old fire road, the trail is not particularly scenic, but it’s what awaits at the top that is worth the climb.

As you get close to the top of the 1.6-mile trail, you come upon massive and eerie, castle-like ruins. It is the remains of the Overlook Mountain House, a hotel that was under construction in the 1920s but never finished.

Since my husband and I hiked on a misty and rainy day, the ruins were an incredible place to explore and take some really cool photos. Although I do admit, it all felt a bit spooky!

A few hundred feet past the castle and up an incline, you arrive at the lookout point that makes the entire hike worth it. Spread out below is a breathtaking view of the Hudson Valley and the Catskill Mountains. On a clear day, there is visibility for miles. Unfortunately for us, all we saw was a white wall of mist!

There is also a fire tower on the property that you can access and climb up a few stories for an even better vantage point. Because of the inclement weather, we opted out of that, but you should check it out if you’re there on a clear day.

Stop #2: A Kitschy Hotel in the Catskills Mountains

 After spending a couple of hours in the wind and rain, we were ready for some R&R. We headed to our home for the night, the Roxbury Motel. Located in historic Roxbury, about 40 minutes from Woodstock, the Roxbury Motel & Spa is a kitschy and fun alternative to a lot of the hipster boutique hotels that have popped up all over the region. While we love places like that as well, we wanted to try something new this time. Also, the Roxbury is one of the only hotels in the area that lets you reserve a room for a single night on weekends.

After getting settled into our Farah Fawcett themed room, we donned our bathrobes and spent some time warming up in the sauna and hot tub at the spa. It was the perfect antidote to our cold and wet morning.

We also spent some time exploring the hotel property, which is full of interesting art sculptures.

Stop #3: A Cozy Dinner Spot in the Catskills 

 The dining scene is very limited in Roxbury. Chappies, a quick stroll from the hotel, has good, all-day fare, but we had been tipped off by a local about a place in Phoenicia that we wanted to check out. We jumped back in the car for the 20-minute drive and had dinner at Peekamoose Restaurant and Tavern. It was the perfect spot for a chilly evening. The atmosphere was rustic and cozy, and the comfort food was outstanding. We will definitely come back to this restaurant!

Road Trip to the Catskills: Sunday

Stop #4: Breakfast and Antiquing in the Catskills

We used to love visiting Sweet Sues in Phonecia for breakfast. (Their pancakes are to die for.) Unfortunately, they are closed now due to COVID-19.

If you’re up for a bit of a drive to the western Catskills, I highly recommend hitting up the adorable town of Livingston Manor. There are a couple of great breakfast/lunch spots here. First is Main Street Farm which is great for breakfast and lunch sandwiches, plus the shop is stocked with basic groceries and local goods from the region. For lunch (or dinner), I highly recommend The Kaatskeller for amazing pizza and salads. Both places are open now, even with COVID-19, but masks are required. Kaatskeller has a large outdoor garden where you can eat your food, and Main Street Farm is take-out only, with limited seating outside.

You can’t drive far in upstate New York without bumping into one antique shop or another. We came across Rick’s Antique Barn, about 15 minutes outside of Roxbury. The 3-level shop was packed with old furniture, knick-knacks, and oddities. Of course, we didn’t leave empty-handed! We purchased an old silver bucket we plan on filling with ice and cold bottles of beer for our next BBQ.

Stop #5: Ramen and Window Shopping in Woodstock, a Quaint Town in the Catskills Mountains

After a bit of shopping, we headed back to the town of Woodstock for lunch. We had read positive reviews about Yum Yum Noodle Bar, so we wanted to give it a try. It was another cold and rainy day, and the hot ramen hit the spot. Even better, I was thrilled to see another restaurant in the area offering gluten-free dishes on the menu as well.

After lunch, we walked around the town for a bit, doing some window shopping. We would have spent more time there, but the skies opened up and it started pouring again, so we jumped back in the car to slowly make our way back to the city.

Stop #6: An Animal Sanctuary in the Catskills Mountains

On our way home, we stopped in Saugerties at the Catskill Animal Sanctuary. Since my husband and I are both animal lovers (Did I mention we have a dog and 3 cats?!), this place was one of our trip’s highlights. It’s a 148-acre, idyllic refuge for farmed animals rescued from cruelty, abuse, and abandonment. Between April and October, they give daily tours, and it’s a very kid-friendly place. While there, we spent time with cows, pigs, hens, roosters, llamas, horses, goats, sheep, and bunnies. It was the perfect way to end our weekend!

Now I’d love to hear from you. Have you been to the Catskills or the Hudson Valley? If so, what are your favorite spots? Where do you stay, and what do you love to do? Please share your recommendations in the comments below!

Happy Travels!

Related: Live in the NYC area? Check out my North Fork Travel Guide and my Saint Michaels, Maryland Travel guide for other great weekend getaways.

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