Take This Road Trip To The Most Charming Catskill Mountain Towns In New York
By Christy Articola|Published June 23, 2022
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Christy Articola
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Christy Articola has lived in Colorado since 2013 and considers herself a Centennial State enthusiast and expert through and through. She's based in Denver metro, but over the past decade, she has traveled to every corner, river, village, park, town, and city in the state and continues to explore it deeper and further whenever she can. Christy simply can't get enough of Colorado, and loves sharing all her adventures with you through Only In Your State! She graduated with a degree in journalism from Fordham University and is thrilled to be working as a full time travel writer for this and other sites - she finally found her perfect niche - and is so grateful for that.
The Catskill Mountains are beautiful at any time of year, and nestled among these gorgeous peaks are many mountain towns that are small on population, but big on charm. If you’re looking to explore the Catskill Mountain Region, visiting the best of these towns on a weekend road trip is a great way to see some memorable sights and to get a taste of the unique flavor of this area. Read on.
This Catskill Mountain road trip creates almost a complete loop. We have it starting in Windham here, but you can start anywhere and you'll end up pretty close to where you began.
The driving portion of this road trip will take about four hours, but you'll likely want to stop and dilly dally in each town as you pass through. You'll probably want to make this a two or three-day trip so you have time to enjoy each of these small mountain towns.
Some people overlook the Catskill Mountains because they aren't as large as New York's Adirondacks, but they are just as lovely, if not more.
The starting point of this road trip is Windham. Although this small town of about 1,700 residents is best known for winter skiing, you'll love it in the other seasons as well. There are numerous historic homes in Windham, and you and your companions might enjoy a walk or bike ride on the multi-use Windham Path Trail.
Head down Route 296 for about 20 minutes to Tannersville to enjoy a tiny town that many consider to be their favorite of all the Catskill villages. Tannersville has just under 600 residents, but there are a number of pleasant shops and restaurants on Main Street.
Phoenicia is even smaller than Tannersville with a population under 400. In the summer, people come from all over to Phoenicia to go tubing on the Esopus Creek. Don't miss it.
Woodstock may sound familiar to you, but believe it or not, it's not where the famous 1969 music festival took place. Still, this town has an artsy, hippy vibe that most find quite charming. With a population of 5,700, this is the largest small town on our list. It's a great place to spend the night if you're breaking this trip up into two or more days.
Bethel, on the other hand, is actually where the 1969 Woodstock Music and Art Festival took place--and most of the town's 4,200 residents are quite proud of that fact today. You can visit the site of the festival and visit a fantastic museum there about it. You can also visit galleries in town, such as the Stray Cat Gallery shown here.
The next town on your road trip is Roscoe, which has less than 500 residents. It's an angler's paradise - five of the nation's best trout fishing streams are in Roscoe, and it is known to many as Trout Town USA. If you get thirsty, stop by Do Good Spirits, shown above, for some high-end alcoholic refreshments.
Margaretville is a small mountain town with a population of just 700. Main Street is especially charming and you'll love strolling along it, imagining the people and activities of days long ago.
The town of Roxbury is home to about 2,300 people. This hamlet is very serious about preserving its history so you can find many attractive historical buildings around town. The Roxbury Hotel, shown here, offers themed rooms that you have to see to believe, and it's a perfect place to wrap up this road trip.
This road trip is so much fun! On it, you’ll visit seven of the very best and most charming small mountain towns in the Catskills. You’ll see that they all have their own unique character and you’ll love them all. Have a great trip!
