The Catskills Town I’ll Always Return to When New York Fall Begins

There’s a certain kind of Catskills weekend I find myself craving when the New York air turns crisp: a small mountain town, a good hiking trail , an afternoon spent rummaging through antique stores , and somewhere cozy to eat and sleep before heading back to NYC. Increasingly for me, that place is Tannersville.

As a lifelong New Yorker , I first came across the village about a decade ago while making my way through a checklist of Catskills and Hudson Valley towns . I was charmed by how much personality was packed into such a small place: a colorful Main Street lined with independent shops, endless mountain views, and easy access to nature, from woodsy trails and lakes to its far more popular neighbor (and ski hub), Hunter, just five miles away. At the time, though, I mostly passed through; there weren’t many places to stay that made me want to turn a stop into a full weekend .

When I finally returned in 2023, that had begun to change: A fresh crop of inns and hotels had opened or reopened, Airbnbs had seemingly popped up at every turn, new restaurants had arrived, and suddenly Tannersville felt like somewhere I could build a whole trip around. I’ve been coming back every fall , with a sprinkle of winter trips thrown in, ever since, usually for quick, cozy weekend getaways when I want a taste of the mountains without straying too far from home. Depending on traffic, the drive can take anywhere from about 2 hours and 15 minutes to 3 hours from Brooklyn, and it’s worth every minute of the commute.

Here are all the reasons why Tannersville should be on the top of your upstate New York bucket list, and how to fill your itinerary while you’re there.

An aerial view of Tannersville, where the colorful Main Street meets the mountains to play

There are a whole lot of charming upstate towns, and of course, they all have their time and place. But Tannersville has been a Catskills destination in one form or another for generations, first growing around the tanning and lumber traders before becoming a popular vacation town after two historic railroads reached the village in the late 19th century. The colorful town you can visit today is part of a much newer chapter, earning the fitting and sweet “ Painted Village in the Sky ” nickname. However, a big part of the draw is that the region never feels entirely new: Longtime shops and establishments still share Main Street with fresh places to eat, drink, and shop, while the surrounding mountains keep nature at the center of any visit.

It appears the secret’s out, and others are hopping onto the Tannersville trend too. Airbnb data shows that searches for fall weekend rentals in this town are up by more than 15% year-over-year. It makes sense, given the area's endless supply of stunning mountain homes . But if a house rental isn't your speed, don't worry, there are plenty of charming boutique hotels to choose from.

Checking into Tannersville's Deer Mountain Inn means resting your head amongst artsy, rustic-chic design.

One of my favorite parts about this village is that you can center your stay around some of the coziest, most design-forward home bases in all of upstate New York. There are intimate inns tucked into the woods, bucket-list A-frame Airbnbs , and happening hubs just beyond Main Street available for check-in at your convenience.

Hotel Lilien is my pick for staying right in the middle of Tannersville’s newer, more aesthetic-forward corner. Set in a restored historic property, the 22-room boutique has become something of a local living room, with a cocktail bar, wood-burning stove, library , pool table, and plenty of corners for cozying up. Deer Mountain Inn is the one I’d choose for true respite. Perched above Tannersville on 168 acres of meadows and woods, it has just six rooms in the main lodge plus four standalone cabins, with antique furnishings, William Morris textiles , fireplaces, firepits, trails, and mountain views for days.

I'm dying to check out Hotel Mountain Brook , a more traditional upstate getaway. The Adirondack-style lodge sits just above the village, so you get the feeling of being up in the mountains but are close enough to walk into town. Its complimentary breakfast, cozy common spaces, mountain views, fireplaces, and easygoing vibe make it well suited to a low-key weekend where you hike during the day and come back ready to do very little.

If you don’t mind crossing into neighboring Hunter, Scribner's Catskill Lodge is worth the short drive: It has a more expansive, destination-resort feel than the smaller Tannersville inns, with 38 rooms, a restaurant and bar, seasonal pool, sauna, firepits, and lots of room to sprawl.

Tannersville's size means you can eat your way through much of the town on foot, but there’s enough variety that your itinerary doesn’t have to revolve around the same mountain-town burger and beer. Start your day at The Pantry On Main , a Main Street breakfast and lunch spot with go-to provisions, before heading out for a hike or stroll. For a morning coffee or something quick before getting on the trail, add Deja Brew to the list for coffee, breakfast, sandwiches, and pastries. And for a post-hike refuel when all you really want is a burger, fries, and ice cream, head to the retro-inspired Mama's Boy Burgers .

For something more casual, Pancho Villa is the long-time Mexican restaurant known for tacos and tequila. Brave the Flames is a good bet for unfussy, made-from-scratch comfort food in a casual setting, with everything from burgers and sandwiches to all sorts of rotating specials. Lucky Catskills is a newer favorite that brings Asian flavors to the village with hand-folded dumplings, ramen, rice bowls, and tasty steamed buns. (You might also be familiar with its Hudson Valley location in Kingston.)

Then there’s Last Chance Antiques and Cheese Café , a Main Street institution since 1971 and one of those places that is almost impossible to categorize: part restaurant, part cheese and candy shop, part antique-filled curiosity stop, part bar, and yes, part live-music venue. Come for lunch or dinner, browse the shelves, and, in winter, indulge in its famed après-ski fondue.

Fireplace dining awaits at Deer Mountain Inn, with cooking led by a James Beard Award semifinalist.

For a “big night out,” don’t miss dinner at Deer Mountain Inn , whether you’re staying there or not. Just outside of the town center, its restaurant serves seasonal and local cooking led by James Beard Award semifinalist Chef Cowin Kave, with a stellar wine and cocktail program in a cozy dining room centered around the fireplace. The menu regularly changes based on what’s available from local farms and producers.

Lucky Catskills is a new favorite of mine that brings Asian flavors to the village.

Shopping at Camp Catskill includes lots of cute local merch.

Tannersville is the kind of Catskills town where “playing” can mean anything from digging through a room of old furniture to hiking above the clouds, and I just love that the two can happen in the same afternoon. The village is famous for its almost Wes Anderson, like Main Street, and I’d argue it gets even more fun when the seasons change: Fall leaves make those pastel painted storefronts pop, while early snowfall turns the whole place into a little mountain-town snow globe.

The antique shop on Main Street is one of my favorite stores.

I absolutely adore Tannersville Antiques and Artisan Center on Main Street. Housed in a 19th-century building with more than a dozen dealers, it’s packed with vintage furniture, artwork, jewelry, home decor, and the wonderfully random finds that make browsing an activity. Whether you’re staying there or not, put Hotel Lilien on your fun itinerary. With live music, DJs, and a social scene that hangs out around the pool table and cocktail lounge, it's a vibey hub, even on weeknights.

I’d also make a little time for Mountain Top Library , located right in the village. Founded in 1900 and now housed in a former Catholic church, it’s a community hub with educational, artistic, and musical programming, a charming stop if you want to see a more local side of the mountaintop beyond the weekend crowd. And always keep the lighthearted Space Brew Pub in your back pocket for locally crafted beers and classic American food.

For good views and fresh air, go on a light hike around the Mountain Top Arboretum Loop

In my opinion, the nature that surrounds Tannersville is at its peak during the fall, making it a great destination for foliage chasers or anyone looking for a burst of crisp, clean mountain air. For first-timers seeking big Catskills scenery, the Escarpment Trail to Kaaterskill Falls is the classic, with dramatic overlooks and waterfalls that explain why people have been coming to these mountains for generations.

For something less strenuous, the Mountain Top Arboretum Loop combines the artsy arboretum with tame meadows, ancient hemlock groves, and a hidden mountain-top marsh, while the Scutt Road Loop (via Badman Cave and Artist’s Rock to North-South Lake) is better for a more rugged day, with forest, rocky terrain, caves, overlooks, and glittery (or frozen) lake views.

Riverside hiking is your best friend in Tannersville, especially in the fall.

Whatever you do, don’t skip Rip Van Winkle Lake Park , just a short walk from Main Street. The lake and surrounding park have a bike path, playground, skate park, basketball and handball courts, volleyball, and disc golf. (It’s lovely for families traveling to the region too.) The park taps into the region’s old folklore, named for the legendary character said to have woken from his 20-year sleep in the Catskills.

If you come in winter, go skiing . Hunter Mountain is only a few miles away, making Tannersville an easy base for a ski weekend : Spend the day on the slopes, then come back into the village for dinner, drinks, and all the more comfortable parts of winter that don’t require strapping anything to your feet. And in summer? Those same mountains turn into a playground for hiking, biking, swimming , fishing, and getting out on the water.