New York's 5 Most Charming Towns With Cozy Vibes In The Catskill Mountains

The Catskill Mountains in upstate New York are neither overhyped nor too remote, making them perfect for a cozy getaway in a mountain lodge or a historic chalet. Astride the mountains are lots of small towns flush with a history going back to 17th century Dutch settlers, turreted Victorian homes, and nostalgic general stores. The Catskills region has been nicknamed "America's first vacationland" for its association with early incarnations of mountain resorts — the first grand resort hotel in the country was the Catskill Mountain Resort, opened in 1824. Ever since, towns in the Catskills have attracted visitors for their historic charm and access to natural beauty, with waterfalls and winding mountain roads among their roster.

What makes for an ideal Catskills town? On the surface, access to natural beauty and a storybook look are an initial litmus test, although, to be fair, there's an abundance of Catskills towns that meet such criteria. Beyond those baseline qualities, some other factors that cut a little deeper into what visitors connect with are the towns' distinct local cultures, ease of getting around, and stores or local fixtures that keep the town cozy and communal year-round. After all, while a trip to the Catskills might be paired with a mountain excursion or watersports, it's what's offered within the towns themselves that make them stand apart from other mountain regions in the Northeast. Sourcing from past visitor experiences and reviews online, we selected five towns that have a unique appeal and will make you want to come back to see them in every season.

Many people might associate the Catskills with a kind of Bohemian spirit and artistic bent, and that impression is owed largely to Woodstock. As a quirky, artsy town full of farm-fresh food, Woodstock has been a cornerstone of the area's creative reputation and sits in the Southern Catskills, a straightforward two-hour drive from Manhattan. The famed Woodstock music festival of 1969 didn't actually occur in Woodstock, but it kept the town in its name for a reason: Woodstock had become, by that time, known for its creative scene, as reported by Time. You can still see this legacy in downtown Woodstock today. One must-visit stop is the Woodstock Artists Association & Museum (WAAM), dubbed the "local Louvre" of Woodstock and active since 1920 as a showcase of local artists. It holds 4.6 stars from Google reviews and is open Thursday through Sunday, with rotating exhibitions that span photography, sculpture, and painting.

Woodstock's pedestrian thoroughfare is Tinker Street, running straight across the town with most of its quaint shops and pubs. The whole street is just under 2 miles and is an enjoyable walk. "You'll find tons of eccentric shops and dining options," blogger Jen on a Jet Plane said of the street. "I recommend strolling around at your leisure." A few craft stores and galleries pepper the street's east end by WAAM — the Woodstock Emporium & Holiday Haus has a 4.6-star Google rating and is a good option for finding a local craft or souvenir. On the other end of the street, the Tinker Street Tavern is a notable spot that opened just in 2021 and already has around a 6,000-strong Instagram following. The venue hosts live music in a house built in 1897.

Windham in the Northern Catskills is largely known as a resort town, revolving around the year-round Windham Mountain Club, though it also has an adorable downtown strip punctuated by unique local fixtures including a country store, beer hall, and art galleries. Inside Hook called the town "the coolest little mountain town in the Northeast." A bit further up than Woodstock, you can get to Windham in a two-and-a-half-hour drive from Manhattan.

The key to Windham's dreamy mix of main street and mountain charm is its picturesque, 19th-century village feel. The town rose to eminence in the mid-1800s, according to the Windham Chamber of Commerce, and there are still traces of that bygone era in the town's buildings and atmosphere. Its Centre Presbyterian Church, dating to the early 1800s, is listed on the National Register of Historic Places. Today, it's a community center and concert hall that hosts the Windham Chamber Music Festival. From the former church, you could walk to the Catskill Mountain Country Store in about 10 minutes. Listed among the most nostalgic upstate New York general stores by CNY News, the country store sells everything from locally made jams to apparel. It also has a farm animal rescue zoo.

For visitors who want to spend time outdoors, the Windham Mountain Club is no doubt a major draw of the town, offering skiing, snow tubing, and golf. However, you don't need to spend on a lift ticket or resort pass to cash in on Windham's nature. The 1.5-mile Windham Path is a lovely public walking and biking path along the Batavia Kill stream that winds through town, passing through woods, covered bridges, and wildflower-filled meadows — the Windham Area Recreation Foundation offers a checklist of all the wildflowers you could spot on the path.

Saugerties sits between the Catskill peaks and the waterfront of the Hudson River, complete with a lighthouse and creek-side beach. USA Today named Saugerties the second-best small town in the Northeast for 2025, citing its creative energy, eclectic shopping, and scenery. You truly get the best of everything in Saugerties, whether you're looking for a small-town bar to settle into with spirited locals or a solitary escape into nature, all within a two-hour drive of New York City.

One perk that boosts Saugerties' "cool" status is its treasure trove of vintage stores. Nearly all of them are clustered around the intersection of Main Street and Partition Street, the highly walkable heart of Saugerties' downtown. A Reddit user recommended The Well as one of the best thrifting spots in the Hudson Valley, describing it as "small but fantastic, best prices in the area, best people, rare but great finds." Another must-stop is the Saugerties Antiques Center, which holds 4.4 stars on Google and has a vast selection of items for all budgets. After browsing, you could stop by The Dutch just across the street — an iconic tavern that dates back to 1933.

When you want to venture beyond the downtown area, the historic Saugerties Lighthouse can't be missed. The lighthouse was built in 1869 and has since been restored to a bed-and-breakfast, but it's also open for visitors and public tours. To reach it, you have to make a 0.5-mile hike on a trail through the Ruth Reynolds Glunt Nature Preserve, encompassed by a tidal wetland. The trail is open every day of the year, and ticketed tours are offered on Sundays during the summer.

If you want to get into the more secluded, misty highlands of the Catskills, then Big Indian is ideal. Big Indian is flanked by some of the highest Catskill peaks, with Slide Mountain (the tallest of them all) to its south. The hamlet (two to three hours from NYC) has just over 400 residents, according to the last update from Zip-Codes.com, making it more pastoral than its artsy counterparts. But what earns it recognition as one of the best small mountain towns in the Catskills is its breathtaking hiking trails, cozy cabin lodgings, and one award-winning restaurant.

That restaurant is the Peekamoose Restaurant, the sole establishment visible on a stretch of Route 28, framed by forested mountaintops. The restaurant has been name-dropped in Michelin's guide to the Catskills, and it won a Small Business of the Year award in 2022 from the Ulster County Regional Chamber of Commerce, as reported in The Daily Freeman. It's set within a rustic farmhouse, intimate and warm, with decor made from fallen wood found onsite. The menu changes daily but specializes in high-end American fare, though you could also just stop in for brews in its tap room.

Staying overnight in Big Indian is a treat, as there are several cabin lodgings available that give you a quiet mountainside perch to sit by a fireplace and stargaze from the window. One well-reviewed option is the Cold Spring Lodge, which one Tripadvisor reviewer recommended, stating: "The cabins are very clean and have the iconic cedar smell that makes cabins so cozy." Those interested in hiking during their stay will find some incredible views on the 5.4-mile Balsam Mountain trail, which leads up to the mountain peak.

One of the most visually distinctive towns of the Catskills, Tannersville is nicknamed "the painted village in the sky" for its brightly painted historic buildings along Main Street. As recounted in The New York Times, the colorfully painted Victorian homes of Tannersville started acquiring their vibrant palette in 2003, when the town sanctioned the idea, led by a local artist, as a revitalization effort. As a testament to the initiative's success, the colorful homes are now a main highlight of its appeal among trip guides and planners.

Tannersville's charm runs deeper than its painted exteriors, though. One thing the painted houses might reveal to visitors is just how walkable its Main Street is: Within a 30-minute walk, you can see most of the strip, with arts centers, cafes, and restaurants all conveniently grouped along the main drag. A unique place to stop in is the Last Chance Antiques & Cheese Café, which has amassed over 1,000 Google reviews while holding a steady 4.6-star rating. Inside, it's a rustic, antique-filled restaurant with a particular focus on gourmet cheeses. It's also got an extensive beer menu. Across the street is Maggie's Krooked Cafe & Juice Bar, described by one Google Local Guide as: "The perfect stop for a good cup of coffee and homemade muffins that will blow your mind."

Tannersville is a practical base point for exploring some of the Catskills' best natural landmarks, too. The towering Kaaterskill Falls are just a 10-minute drive outside of town, and North-South Lake is a couple more minutes beyond. If you're coming from NYC, the fastest route will get you to Tannersville in just over two hours by car.

To pin down just five towns in the Catskills that are worth visiting is no small task, but we selected five that most embody the region's cozy allure and offer something uniquely charming. We looked for towns with a strong sense of character — whether that be Woodstock's artistic ties or Saugerties' antiques scene — and interesting local history. The coziness factor follows from walkable streets, welcoming dining and lodging options, and small shops or galleries that add to a warm community atmosphere. Our selection process drew on online visitor reviews from Tripadvisor and Google, coverage in news outlets, and tourism board resources.