Hello travelers! My name is Nikki and I grew up on Long Island, New York in a small beach community. Growing up by the beach helped shape my love for the outdoors and the ocean, which gave me an eye for photography.
I never traveled much outside of the Caribbean and Florida but dreamed of exploring the wider world. It wasn’t until my junior year of college that I was able to fulfill that dream! I studied abroad in Europe during my second semester and throughout that time I was able to visit 13 countries.
Even though the countries I visited were close geographically, I was fascinated by their differences. Whether it was cultures, architecture, vistas or even international trends – I wanted to soak it all in! I took a huge amount of photos while I was abroad and wanted to share those memories with others, which inspired me to start my Instagram: @tripofthemonth_.
On this account I share my travel stories, tips and post a new destination every month. After returning from Europe, I purchased a large world map and began placing colored pins on it – not of destinations I was planning to visit but of places I have been to so far. My end goal is to fill as much of this map as humanly possible. Years later, I still have that world map on my wall.
4 Amazing Nights in Roxbury, New York
Looking at the empty spaces on the map, I realized I have so much to explore in my own country! During the peak of the pandemic there wasn’t much international travel I could do, so I decided this was a great opportunity to explore an area of New York that I haven’t traveled to yet.
After doing some research I found that the Catskills was an easy drivable destination about 2-3 hours from where I live. From there I narrowed down the primary location for the trip to Roxbury. I stayed in Roxbury for four nights and I felt that was the perfect amount of time to spend there.
Over this period I explored adorable towns, stayed in a fabulously cool hotel/lodge and hiked some awesome trails. Roxbury could be best described as a quaint town (with a population of around 2,400 people) that is filled with charm and has an incredibly welcoming feel to it. Driving down the street felt like I was driving through an old small town in a movie!
Between the serene hiking trails, the amazing antique shops and all the activities quickly available nearby – this is definitely a place you are going to want to add to your weekend getaway list. Even though it’s a small town there was enough to keep me entertained for my stay. If you are looking for an excursion in upstate New York, then Roxbury should be on your list!
Staying at The Roxbury – Contemporary Catskill Lodging
If you want to experience the best of Roxbury then I recommend staying at The Roxbury (website here). I have never stayed in a place like this and it amazes me how unconventional and enchanting the entire atmosphere is. It’s not just a place to spend the night – it’s an entire experience in itself!
The Roxbury consists of two hotels down the road from each other: The Roxbury Motel, which is where I stayed, and Stratton Falls Cottages. There are 43 rooms and each room offers its own unique theme, ranging from Austin Powers, to The Wizard of Oz, and everything whimsical in between. It’s great for families with young kids and great for adults as well!
The room I stayed in was called “The Shagadellic” and was the very first room they created. It had a kitchen stocked with everything, a dining area, a living room with a couch and a full bed, and a separate bedroom with a king sized bed. I was in awe of how much detail the owners put into creating these rooms, they all fit their specific themes so perfectly!
Even the bathroom stayed true to the theme. I am already looking forward to checking out one of the larger cottages with a group of friends. Additionally, my favorite memory of this stay was just exploring the surrounding areas encompassing The Roxbury and our room. At nighttime the motel is lit up with various color changing lights – it was extraordinary!
There is also a private hiking path down to a secluded waterfall that only guests of The Roxbury have access to. The hiking trails really make you feel one with nature, especially when walking along the boardwalk path up in the trees. The trails are mild and when you arrive at the base of the falls it’s so peaceful. If you want to stay at The Roxbury I recommend booking early.
TripAdvisor listed this lodge as one of the Top 25 Hotels in the US. HGTV stated that it’s: “One of the most amazing hotels in the country”. So this spot books up quickly. When I visited there was only one room available.
Hiking to the Wonderful Kaaterskill Falls
While there are plenty of amazing hiking areas in the Catskills, a great location I would personally recommend is Kaaterskill Falls, which is about a 40 minute drive from The Roxbury. Kaaterskill Falls is one of the most beautiful waterfalls I have seen. It’s a stunning double waterfall with a height of 260 feet making it even taller than the impressive Niagara Falls!
There are many different starting areas and trails to different vantage points, making it a great location for beginners and experienced hikers. There is a top observation deck where you can see amazing views of the waterfall but there is also a trail that leads to the base of the falls. You are actually able to stand beneath the falls and swim in the water. I suggest arriving early or coming during a weekday as the parking lot fills up fast.
Adding Woodstock, NY to your Travel List
If you are looking for other things to do in the Roxbury area, I would highly recommend visiting the town of Woodstock – known for its shopping and art. Woodstock is a little under an hour away from Roxbury, so I made sure to make a stop on my way home to window shop and explore.
There are so many shops, breweries, restaurants and galleries. I think it’s worth the drive, even just to look around. The people in Woodstock continue the vibe of the 60’s and just like Roxbury it’s also a quirky place.
Best Time of Year to Visit Roxbury
The best time of year to visit Roxbury is in the summer or fall. I visited in the summer and the weather was great to hike and explore the surrounding area. I also suggest visiting Roxbury in the fall, so you can see the leaves change color and the climate might be cooler for doing longer hikes.
Final Thoughts on Visiting Roxbury
With the ongoing pandemic, there are fewer opportunities to travel for many of us. A weekend getaway trip is just what I was looking for to escape the reality of what felt like the never ending work week. For anyone in a similar situation, or if you are just looking for a unique, easygoing and unconventional trip, I hands down recommend checking out Roxbury, New York. You will be presently surprised by this small town in the Catskills!