AN INSIDER’S GUIDE TO THE ULTIMATE CATSKILL SUMMER
Berry picking at Grieg Farms
I’ve gone over this list a half dozen times in the past two days alone, and am still not quite sure how to break it down. Initially I thought of separating it along the lines of the river, keeping half of it in the Catskills, the other half in the Hudson Valley, but seeing as no matter where you stay you’re going to be doing some driving, I figured I’d keep it to categories.
If I were you I’d try to find a place to stay somewhere between Woodstock and Phoenicia as you will then be equidistant to almost all adventures . That said, the two best hotels in the region, Piaule and Inness, are both a bit off-axis from the sweet spot. Either way, you’re going to need a car or a friend that drives and doesn’t get pissed off that you don’t.
Lastly, the prime time for heading up here is Wed-Friday in the summertime. Most things are closed Tues-Wed, and most things are insufferable Sat-Sun because of people like you coming up. Otherwise, come for a couple weeks and just stay put on the weekends in whichever idyllic haven you choose to hole up in, venturing into the towns only towards the end of the week.
But no matter when you come up or where you stay, I guarantee you’ll fall in love. This area is so so special for a thousand different reasons, it’s why I’ve called it home for close to twenty years. From hidden waterfalls to bountiful farmstands, honky-tonk nights at The Pines or breakfasts in Kinderhook, gentle hills and warm hearts, it’s all just beyond awesome, and just a couple hours from the city. Here we go…
Bovina’s sweeping skies and rolling hills
THE AREAS
Okay, here’s a very brief rundown of all the little micro-zones that comprise upstate.
Woodstock -The epicenter of the Catskills. Yes, Woodstock like the festival, and no, the festival didn’t take place here (the farmer whose land it was supposed to be on got spooked at the last minute and they chose to move the concert down to Bethel, an hour away, but by then the iconic poster had been printed and well…there you go). Despite a half-dozen stores still clinging on too dearly to the summer of ’69 iconography, there is a great blend of classic New England small town and I-ate-too-much-acid weirdness.
Hudson - I aways tell people I live on the wrong side of the tracks, with the Hudson River being the tracks. Well, the town of Hudson is on the right side. While the Catskills are all about rustic mountain life, swimming holes in the summer and family-run ski resorts in the winter, Hudson and the surrounding Valley are all about expansive farmland and sprawling estates. It’s for fancy people. But we like fancy and there are some of the best farmstands and restaurants I’ve ever been to around here.
Tannersville - This town is stuck at a crossroads. On the one hand it offers conveniences like a great little bakery, burger shack, and gift shop along with access to nearby hikes and waterfalls, on the other hand it’s adjacent to the monumental Hunter ski resort and throngs of Hassidic enclaves that shack up for the season. Still worth a visit for a Coke float at Mama’s Boy after hiking Huckleberry Point or a chubby squirrel pastry at Shandaken Bake en route to a nearby swimming hole.
Kinderhook - Just North of Hudson, we discovered this town a couple years ago, little more than an intersection with an exceptional restaurant and gift shop, and two world-class art centers. Jack Shainman repurposed the local elementary school into a massive single-show gallery, while the nearby Art Omi boasts over a hundred acres of site-specific contemporary art.
Andes and Bovina - The farthest points west that you’ll travel, these two sleepy towns are up and over the Catskills’ mountain range, existing in a timeless bucolic landscape that feels closer to Vermont in the 19th century. Old dilapidated barns collapse onto one another, cider houses and farms dot the hillsides, while pristine lakes await your canoe.
Miranda Brooks’ wild, lush landscaping at Inness
HOTELS AND GREAT RENTALS
Piaule Hotel Tucked into the woods near the northern town of Catskill, this architectural masterpiece is the region’s answer to Utah’s mythic Amangiri. A handful of exceptionally-appointed, minimalist wooden cubes with massive windows looking out onto the forest, spaced out around a communal space that houses a restaurant, spa, and lounge areas. It’s as perfect as it gets.
Inness Designed by NYC expat Taavo Somer (creator of Freeman’s Alley a generation ago), this sprawling estate feels inspired by a mix of Hudson Valley farmland and English countryside, perhaps due to the landscaping by British visionary Miranda Brooks. Cottages dot the expansive fields and golf course, while a restaurant and bar at the top of the hill provide a social hub for the area. You can book a room, a house, a staycation or a wedding, either way you can’t go wrong.
The Henson A bit out of the way in the northwestern town of Wyndham, this re-vamped little inn is home to super chef Jeremiah Stone’s latest, Matilda. While I haven’t stayed in the rooms, I had one of my best meals ever upstate at the restaurant.
The Deer Mountain Inn Imagine the summer compound of that rich oil baron uncle you never had, and that’s what you’ve got at the DMI. Actually, the compound belonged to the Colgate family (the one whose name you see every morning at your bathroom sink) and a dozen years ago some enterprising folks decided to convert it into a very intimate ten room hotel, alongside a lovely restaurant and extensive hiking trails. It’s a bit darker than the other two choices but pays greater respect to the traditional Catskill aesthetic. We love coming at least once a summer for dinner on the porch.
The Maker Hotel and Rivertown Lodge In my mind the main reason to head upstate is to escape the city, but if you just can’t stand the quiet of country life and need to walk down a block to grab your morning paper and coffee, then check out these hotels across the river in the heart of fancy-pants Hudson. The Maker’s got a hint of Bowery Hotel aesthetics while Rivertown is brighter and more modern, but both are a stone’s throw from great restaurants and mid-century antique shopping.
For a full locals experience though, renting a spot is the best choice. Below are a few great ones that in all likelihood are already booked up for the entire summer but you should earmark for future visits…
Brian Toll’s Eureka at Art Omi
ACTIVITIES
ART
Art Omi This exceptional contemporary art park boasts permanent works by Dan Colen, David Shirgley, Pippa Garner and countless others, while a main pavilion hosts a yearly temporary show. I would actually try to visit this place in the fall when the leaves are changing and the weather cools. In mid-summer it can get swelteringly hot with very little shade to be found.
Jack Shainman Gallery A space as impressive as any Chelsea gallery and three times the size, Shainman puts on one single-artist retrospective each summer and fall, spreading the work over three floors of Kinderhook’s former elementary school. It’s a ten minute drive from Art Omi and around the block from our favorite breakfast spot, so you can make a perfect day of it all.
The Campus is yet another elementary school taken over, this time by a collective of five NYC gallerists. The renovation on the space is non-existent, leaving you with a dilapidated shell of a public school housing works by Jenny Holzer, William Forsythe, Cecily Brown, and literally hundreds more. It’s a bit overwhelming in scale, a bit hot and humid in the summer, and all in all, worth the trip!
Opus 40 A monumental work of outdoor art that took a lifetime to accomplish, this space is just a couple minutes outside of Woodstock and also hosts periodic concerts throughout the summer.
Bard The college campus features the Hessel Museum, a music center designed by Frank Gehry, and miles of idyllic walking trails open to the public.
DIA Beacon a bit of a shlep, half-way between the city and Woodstock, this museum is a greatest hits for artists like Dan Flavin and Donald Judd who all created site-specific works for the institution.
MASSMOCA and The Clark Institute Ok, these are a couple hours away but well worth the overnight stay at the fun Tourists Welcome motel. From a dozen of James Turrell installations to endless murals by Sol Lewitt, the MassMoca is just AWESOME. Just make sure to individually book the Turrell rooms well in advance (I recommend the first slots in the morning so you can see the rest of his pieces in the quietest way possible). The nearby Clark Institute is more traditional in its collection but worth a visit if you’re in the area.
Foreland Housed in abandoned factories in the town of Catskill, this collection of studio spaces is still a few years away from reaching its full potential but is making a valiant stab at relevance with a mix of co-working offices, temporary exhibits, and an annual outsider art fair.
Paddling along the Pepacton Reservoir
OUTDOORS
Canoeing+Kayaking There are two options here. You can either paddle peacefully on the Pepacton Reservoir which is STUNNING by renting canoes at the Pepacton Bait&Tackle in Arkville (or Susan’s Pleasant Pheasant Farm in Halcott) or you can go for a real crazy adventure kayaking down the Delaware River in Downsville via Al’s Sporting shop. Both offer a great day on the water and are among our favorite activities upstate. If you go on the Pepacton, specify that you want to get the canoes at Shaverton Bridge and make sure to print out a permit first from the DEP. The process is free and takes about 5 minutes, but you need the physical permit printed in advance so plan accordingly! And speaking of planning, definitely pack a cooler for a picnic on the water either way.
Putt Putt Van Winkle This is the stuff of legends. Created by the couple who launched and then shut down the country’s most legendary fireworks show, this Bovina-born labor of love is open around the clock for free rounds of mini-golf. The seventh hole is the 2nd-longest in the world, and the whole course is themed around the story of Rip Van Winkle. The art direction is INSANE, and anyone lucky enough to get a hole-in-one will receive a stunning hand-made trophy in the mail two months later. I can’t impress upon you how special this place is.
The Woodstock Tennis Club is a private affair but non-members can book lessons on their website. There are several public courts in Boiceville, in the high school complex just off Rt. 28. They are open to all on a first-come first-serve basis throughout the summer.
Ashokan Rail Trail the old rail lines around the Ashokhan reservoir have been turned into a beautiful running/biking trail stretching about fifteen miles from West Hurley to Ashokahn. There’s convenient parking, beautiful views, and it’s an ideal place to bike for families. You can rent bikes here.
Accord Speedway A small town race track, perfect for bringing kids on hot summer nights. It’s a noisy affair and I strongly recommend both sitting at the back of the bleachers to avoid smoke and mud splatters, and paying the extra five bucks to be able to go “backstage” and visit the cars up close between heats.
Hudson Valley Renegades A minor league baseball team near Rhinebeck plays games all summer long.
The Catskills’ gentle slopes from the top of Devil’s Path
HIKES
Overlook Mountain A fairly straight-forward (read: dull) hike right out of town, it’s worth it for two reasons: 1. the 360 degree views from the top where you feel like you can practically see NYC and 2. the haunted remains of the long-abandoned hotel 2/3rd of the way up. It’s the Runyon Canyon of the Catskills.
Plateau Mountain via Devil’s Path (Starting at the Devil’s Tombstone Campground on Rt. 214). This one will break your legs and back but getting to the top is soooo rewarding and it’s a relatively quick hike. Not recommended for young kids or out-of-shape parents. Once you get to the lookout continue onwards for your nose to be filled with the smell of fresh pine and your eyes to feast on the multiple lookouts over the following mile or so (it’s not a loop trail so you can technically keep going for a day or two or head back anytime once you’ve reached the first viewpoint at the top).
Huckleberry Point Near Tannersville, this is a great family hike. Not too hard, not too long, and a beautiful pay-off of a view at the end. 5 stars.
Black Glen at the Deer Mountain Arboretum Just down the road from the Deer Mountain Inn, this meticulously-manicured and maintained property features some great trails for strolling. Nothing too exerting or too far, it’s ideal if you have little kids and want to introduce them to the pleasures of hiking.
Giant Ledge There are dozens of great, challenging half-day hikes in Catskills and none of the mountains get much higher than 3,500ft so there isn’t a ton of elevation gain. This one is a local favorite.
Swimming Holes Okay, sorry to end on this note, but here’s where I draw the line. I’m happy to share all my favorite secret addresses around the world with you, but I simply cannot in good conscience give away swimming holes. These are the most coveted spots upstate, and every time a New York Times article or an asshole with an Instagram following publishes one, it is forever ruined by hordes of people. The real secret is to discover one while you’re upstate and then never ever, EVER, under any condition, tell anyone else about it—it’s a far greater crime than wearing white in the Hamptons past Labor Day…
Works in progress at Josh Vogel’s Black Creek Mercantile&Trading Co. in Kingston
SHOPPING
Pidgin A mix of high-end antiques and local finds, this spot in Oak Hill is right out of Architectural Digest. It’s a bit far from everything, but that makes it all the more special!
Black Creek-Kingston/Fern-Hudson/Sawkille-Rhinebeck If you love the BDDW furniture aesthetic as much as we do, these three stores are great finds. Unique, exceptional hand-made wood furniture and sculptural pieces. Black Creek also has a wonderful selection of gifts like wooden bowls, cutting boards, and more.
Warren Street The main drag in Hudson boasts great mid-century stores, record shops, and bakeries. You can easily spend the afternoon here when you’re done brunching at Café Mutton or the Rivertown Lodge.
OK Pantry in Kinderhook sells a beautiful collection of children’s toys, a worldly selection of candy, and the best kitchen staples collection I’ve ever seen. Their chocolate chip cookies are also a force to be reckoned with.
Sundry Tannersville’s first decent store, a great mix of home furnishings for an upstate house. From cast iron skillets to cozy blankets, locally-made candles and hand soaps, the selection and quality is spot-on though you’ve probably seen most of this stuff elsewhere before. Make sure to visit the Shandaken Bake shop next door for tasty morning treats, though they usually tend to sell out before Sundry opens for the day!
RAINY DAY ACTIVITIES
Patel’s bowling alley in Kingston won’t win any design awards, but it’s functional and in a pinch does the trick.
Skate Time - An equally vintage roller rink in Accord.
Kingston Ceramics Studio offers both private and group classes for children and adults of all skill levels.
The Orpheum Theater in Saugherties, and Starr Cinema in Rhinebeck are both run by the same people, while Tinker Street Cinema in Woodstock just went it alone, but all three offer a really great mix of indie and studio films along with tasty concession stands.
Bringing home loot from Montgomery Place Farmstand
FARMS+FARM STANDS
Montgomery Place Farmstand If you closed your eyes and imagined the greatest farm stand of all time, with each baby zucchini’s flowering petals intact and droplets of dew dotting every freshly-picked peach, this is the place you’d be thinking of. I’ve never come across a better farm stand, their produce throughout the season only gets better. Just don’t go on Sunday afternoon when their loot is depleted, instead opt for Thursday or Friday.
Fat Apple Farms in Ancramdale. Unbeatable quality in a picturesque location, this is the place to stock up on frozen meat and fresh eggs for the duration of your trip. All done on a cash-only honor-system basis, the store is open pretty much all day every day, just walk in, pick what you want, write down what you took in the journal, and drop them a payment! Beautiful other farms and stands abound nearby including the iconic Ronnybrook dairy farm.
Churchtown Dairy is one of the most picturesque farms in the region offering the most beautiful glass bottles of milk alongside cheeses and frozen meats.
Pick Your Own. There are three great spots to pick fresh fruit around Hudson. Grieg Farms is the largest and offers the most variety across summer and fall, while Fix Farms has the best peaches and Rose Hill Farm specializes mostly in apples come fall.
Ravenwood This perfectly art-directed barn in Stone Ridge offers a mix of interior decor, flowers, and top-notch produce. They started as food stylists and naturally grew into what they are now, still offering some baked good each time they open their doors. Check their instagram site as their hours/days are infrequent…
Migliorelli a decent back-up in case you need to grab something in a pinch. The selection can sometimes look a bit withered but they have solid frozen meat choices and dairy products.
Sunfrost’s annual Halloween pumpkin display
FOOD SHOPPING
Talbott &Arding founded by the NorCal Cowgirl Creamery folks, it's like Cookbook in LA, or Bi-Rite in SF. From exceptional terrines and prepared dishes, to great homemade poundcakes and local produce, be sure to stock up on their hot cocoa mix, i’ve never found a better one in my life. Their little glass jars of vanilla custard and jam are the greatest treats in the world, the eggs they stock from Kinderhook farms have the brightest yolks, and of all the exceptional charcuterie, their classic Virginia smoked ham is the stuff of legends. We drive an hour out of our way twice a month to stock up here.
Mel A couple blocks away on Hudson’s main drag is the region’s best bakery, offering a ton of breakfast pastries, flavored focaccias, top-notch sandwiches and loaves. Get here early before everything sells out!
Fortunes Ice Cream In the quaint college town of Tivoli, this ice cream shop shines bright with flavors like Halva Honeycomb and Labne Sour Cherry. All the fruit they use is brought in from nearby orchards, all the merch is terrific, and the staff is awesome.
Sunfrost and Cub Market Two wonderful small markets in Woodstock and Bearsville, they are ideal for everything that the farm stand may be missing. Sunfrost boasts a tasty juice bar while Cub Market’s sandwiches to-go are perfect for a swimming hole picnic or break on the hiking trail.
Sunflower Not as quaint, this spot in the center of Woodstock is the Erewhon of the region. They now boast a solid fish dept., along with organic everything, plenty of wellness pills, and a large selection of local beers.
Woodstock Meat Market These guys have come a long way in the past ten years. The place used to sell cigarettes, beer, and greyish beef. They now sell cigarettes, beer, and local hormone-free prime cuts of meat. It’s your best bet in town.
Roasted carrots and charred cucumbers at Brushland Eating House
RESTAURANTS/BARS/MUSIC
The Catskill Pines The social epicenter of the Catskills, this rustic roadhouse offers great drinks, a solid smashed burger, and the unparalleled warmth of its owner, the unofficial mayor of the region, Jeremy Bernstein. With his deep roots in the local music scene, Bernstein has been able to offer The Pines as an impromptu concert haven for folks like Marco Benevento and Sam Evian, with intimate winter shows indoors and sprawling musical summer BBQs on the lawn outside. He’ll even rent out the six bedrooms upstairs to groups of friends for the week so be sure to check in with him if you’re looking to corral the gang for an adventure.
Brushland Eating House Just flawless, from the scenic drive there to the last bite of dessert. This place got us to discover Bovina and we’ve never been the same since. Sohail and Sara who run the place are such a special couple, the food is delicious, the setting magical. Just make sure you book way way wayyyy in advance as word has gotten out about this gem. And if the drive seems too far for one meal, make sure to inquire about the perfectly-appointed guest rooms they rent out upstairs.
Stissing House These guys can’t stop winning awards for their old-world dining room that is definitely the most formal spot you’ll find upstate (again, it’s on the “right” side of the tracks). But the decor is impressive and while the menu can be a bit on the heavy side, it’s worth a visit.
Casa Susanna Another relative newcomer with accolades piled high, this Mexican spot in the quiet town of Cairo is unpredictably hidden inside a refurbished 50s-era motel. With all the hype, it’s best you reserve a week or so in advance.
Silvia The “fancy” spot in Woodstock, it’s a bit pricey and feels slightly out of place in the rustic Woodstock surroundings but the room is beautiful, the food really good, and locals are thrilled to have a proper place for a nice night out. They’ve also opened an Asian spot just off the town center called Good Night.
Morningbird When you’re passing through Kinderhook on your way to Art Omi, stop here for an unexpected Filipino spin on breakfast classics, like a spiced egg sandwich or simply perfect mochi donut. We love love love this spot and the adjacent gift shop, bookshop, and liquor store. We try to take the 1.5 hour drive here at least twice a summer.
Buckhill Farms is wayyyyyyy off the beaten track and is almost a full day’s adventure unto its own, but once you arrive and look at the menu, you’ll feel like you’re 1,500 miles away from home and not 150. Biscuits smothered in sausage gravy, pancakes the size of a dinner plate, and omelettes that weigh more than most pets, this maple syrup farm is a great spot to bring groups of friends, though it is more ideal in the fall months when the surrounding leaves are exploding in color.
Bread Alone One of the most respected bakeries in the Northeast offers traditional breakfast and sandwich options both in Woodstock and on Rt. 28 in Boiceville where they also fire up an outdoor pizza oven on the weekends.
Tinker Street Tacos I LOVE THESE TACOS! The trouble is the owner is a cantankerous crank that takes 23 minutes to assemble a single taco and chooses to only open up two days a week. But if you can get past this you are in for a real treat. Weekends can be spent drinking his incredible supply of tequila and mezcal.
Top Taste A tiny shack in Kingston (NY) slinging authentic Jamaican food, and has been twice nominated for Best Chef in NYS by James Beard!
If you’re a New Yorker that can’t go 24h without craving pizza, I’ve got three incredible choices for you. First is Lola’s in Kingston, from the people behind the Inness Resort. Their pastas and drinks are really good, but the pepperoni and hot honey Neapolitan pizza is an 11/10. More bucolic is Westwind Orchard, which came to prominence as a berry picking spot and cider house but is now best known for their pizzas and other tasty food. A great spot to meet friends from different necks of the woods for an afternoon of lazy drinking and munching. And finally, nearby Westwind is Ollie’s Pizza, a massive space serving a massive amount of pies. But don’t let the size scare you, it’s just as tasty as the other two options (and they now have a second outpost in Kingston).
Drive-in Movies There is a really fun multiplex drive-in in Coxsackie NY and a more throwback single screen in Greenville. Showtimes start at sundown so bring blankets, spin your car around, fold down the backseats and lay down in the back of the car! The Greenville theater may not have first-run movies but they have a first-rate snack bar, including cookies baked fresh and brought warm to your car mid-film! A mile or so past the Coxsackie screens is a roadside ice cream stand that will take you back to summer camp treats after the ballgame.
The Maverick A truly one-of-a-kind concert venue in the heart of Woodstock, it’s like an indoor-outdoor church for classical music. Look up their schedule and buy tickets way in advance. It’s a magical experience.
The Bearsville Theater has just been taken over by the legendary Pete Shapiro, owner of Brooklyn Bowl and the Capitol Theater so the programming is about to get really really good. This legendary venue had sunken to an all-time low recently and it’s great to see a solid lineup already announced. Some of the shows are worth booking a weekend trip around a night out of music.