The four-room inn is loaded with antiques, collected by owners Dorothee Walliser and Diane Ormrod—and they’re all for sale. (Well, almost all.) The constant flow of items coming and going result in an ever-evolving interior at the inn, where friends and designers are sometimes brought in to help decorate the rooms. For example, in Room 48, the walls are hand-painted by artist and longtime friend Steve Willis. (By the way, legend has it Steve freehanded the painting, armed with a bottle of champagne.) The cheekily decorated room is a homage to Joyce DeWitt, the character from the 70’s show, Three’s Company. By contrast, Room 49, is quite a different experience, with the cozy, adventurous vibe of a log cabin. Two twin beds, a huge bathroom, and Adirondack decor including snowshoes, books, binoculars, felted deer, and souvenir pennants decorated the room. “Our friend Todd Carr, whose recent past was the Senior Gardening Editor at Martha Stewart, designed room 49.” Dorothee told us. “He brought a lot of things from a store he used to have in Maine, then filled in the rest with antiques we had around the inn.”
We stayed in the beautiful Room 46, which drew inspiration from the outdoors and the town of Oak Hill. Artist Morris Ardoin designed the interior of this room not only with his own art, but older pieces too. Birch branches from trees in the garden create a woodsy backdrop for the queen-sized bed, and a tree stump acts as a bedside table. The room overlooks the Catskill Creek, where a few benches and chairs encircle an antique wood stove that acts as a firepit.
Before their time as innkeepers, Diane and Dorothee both worked in publishing in New York City. The business duo bought the building in 2014, spent nine months renovating, and opened it in June of 2015. They work tirelessly, maybe even more than in the city—but in a shared sentiment with many other business owners we meet, the payoff is so much more rewarding. “I love the fact that we’re working to create something totally original. We work very hard, but it’s worth it, because it’s all ours. I love the freedom. And the cool part is that we get to meet great new people all the time!” Part of this freedom and ownership means making their own rules, which for Diane and Dorothee, meant making the The DeWitt Oak Hill as dog friendly as possible. All rooms are dog friendly, and the owners even offer free dog sitting while their guests go out. Dorothee explained the policy to us. “I just don’t see why guests should be charged for a dog staying in their room. We request $50 cash deposit per night, but it’s returned after inspection of the room. We also offer complimentary dog sitting during the day and evening.” Dorothee and Diane are dog owners themselves, and guests can definitely expect to encounter their adorable, super friendly pups at the inn. (Within ten minutes of sitting down, we each had one on our laps!)
Perhaps the highlight of the experience at The DeWitt Oak Hill is the long morning ritual here. Guests wake up to the sound of the Catskill Creek as sun pours into the room. The smell of breakfast eventually wafts up from the kitchen, drawing guests out of bed… and what happens next is phenomenal. Diane cooks, Dorothee bakes, and their super-powers combined create 3-course breakfasts to die for. Breakfast goes down in the two-story great room, where a beautiful Hollywood Regency curved sofa is the centerpiece, and a baby grand piano awaits a player. The entire morning routine takes several hours, but time flies at the breakfast table, where guests compare itineraries, chat about common interests, and of course, rave about the food. Their favorite thing to make? “George Weld’s blueberry grunt. George is the owner of Egg in Williamsburg, but he’s also a neighbor in Oak Hill. We use his family recipe. On the more savory side, we also love the avocado feta tartine with poached eggs, smoked salmon and smoked paprika.” If that doesn’t get your mouth watering, then probably nothing will.
After breakfast, you’ll want to explore the area, which is rich in farmland (read: fresh food), beautiful scenery, and activities both indoor and out. We paired up with the folks at Great Northern Catskills (@catskillstourism on Instagram) to create a guide to the area around The DeWitt Oak Hill, including some of the best dining, drinking, and outdoor stuff available to do in the area. Read on to plan your own trip!
What To Do in Oak Hill, NY: See A Movie at the Drive-In, Go Antique Shopping, and Get Inspired by Hudson River School of Painters
Though any time of year is beautiful to visit, fall and winter are special in Greene County because there’s a lot going on, both indoors and out. In town, a spattering of antique shops and boutiques line the streets, each as great as the next. Neighboring building to The DeWitt Oak Hill is the home of record label Dope Jams, an NYC-expat record label and vinyl shop. Owner Paul Nickerson left New York in 2013 after his rent increased threefold, and reopened Upstate the same year. Since then, he’s enjoying the slower pace of life with his online business; opening his shop whenever he wants, and hosting the occasional epic party. (If you’re dying to go, best arrange a time for the shop to be open!) A bit further down the road, The Assemblage is a collection and museum space of artist Norman Hasselriis who lived and worked in Oak Hill for 23 years. More than a thousand of his pieces (a.k.a. “assemblages”) fill every nook and cranny of the space, which is open regularly all summer. (Off-season visits can sometimes be arranged by emailing the owners.) Last, don’t miss I.U. Tripp, an incredible antique shop housed in two adjoining 1800’s general stores. The original building from 1830 is amongst the oldest remaining general stores in America, and retains its historic charm with its many original fixtures. These days, the collection is made up of some newly handmade items—hand-kitted wool socks, throw pillows with 19th century textiles, candles, etc.—but mostly specializes in deadstock items and antiques. Say hello to Chris, who’s taking the reigns at the shop after his parents have run it for 20+ years. His past life as a design director for companies like Ralph Lauren and Tory Burch shines through at I.U. Tripp, whose curated clutter collection could demand far higher prices than they currently do.
Artsy types will appreciate the history behind the Hudson River School of Art, America’s first artistic movement, which was born in and around the Great Northern Catskills. Founded by Thomas Cole, the painter first glimpsed the region from a steamship as he traveled up the Hudson River in the autumn of 1825. He found the vibrant colors of fall to be so inspiring that the began painting them soon after, developing the “Hudson River School” style which combined landscapes with romanticism, and delved into the themes of discovery, exploration, and settlement. Soon after his first trip there, Cole relocated to what’s now the town of Catskill, building the home and studio which remains to this day. Visit the Thomas Cole National Site for a self-guided door through the home and studios, which have been carefully preserved over time. Nearby, the pupil of Thomas Cole, Frederic Church, built a home and studio as well called Olana. The ornate and fascinating Victorian-style property is closer to Hudson, NY and available for tours by reservation. Together, the themes of the stunning scenery of the Hudson Valley and Catskills inspired these painters to create some of America’s finest landscapes. To visit some of the overlooks they drew inspiration from, check out the hikes listed throughout Kaaterskill Clove. The most popular hike by far is Kaaterskill Falls, which inspired Cole’s Falls of the Kaaterskill; we also visited Kaaterskill Clove Lookout, which is just outside of Palenville. (We’d recommend the latter for those who wish to escape the crowds at Kaaterskill.) A short 30-minute hike takes you to an incredible overlook where several mountains meet, creating a rather dramatic landscape. Pack a picnic from nearby cafe Circle W, or stop in for a post-hike meal.
During summer and fall, check out the Greenville Drive-In, a drive-in movie theater just ten minutes down the road from Oak Hill. Open until late October, the retro theater shows classics, as well as first-run movies on the weekends; they also host special events like video game nights and festivals. Food and popcorn are available at the snack shack, while (alcoholic!) drinks are available at the bar. Last, fall and winter visitors should check out the offerings at Hunter Mountain, where visitors can take scenic sky lift rides ($12), or even fly down longest, fastest and highest zipline tour in North America; it’s also the second largest in the world. Riders experience over 4.6 miles of ziplines, up to 3,200′ long and 600′ off the ground. For even more ideas in the area, check out Great Northern Catskills‘ tourism website.
Where to Eat & Drink in Oak Hill, NY: A Woodland-inspired Fairy Tale Deli, Farm-to-Table Diner, Farm-to-Glass Brewery—or Just a Farm!
Next to the The DeWitt Oak Hill is the Yellow Deli, where visitors should eat at least once during their stay. The restaurant is housed in an old opera house at the turn of the 19th century, though the interior would have you guess it’s been there forever. The restaurant is straight out of a woodland fairy-tale: masterful carpentry with live wood edging on nearly everything, macrame curtains and lampshades, and a beautiful hand-painted mural of a forest scene. The food is delicious and the staff is delightful. Great for breakfast, lunch, or dinner from Sunday through Friday.
Farm-to-table lovers will have lots of options in the area, as much of the land in Greene County is farmland, supplying local restaurants and bars with yummy ingredients. Skip the middleman all together and head to Greene Farms, where guests can pick up local groceries, but also indulge in pizza made from farm ingredients. (Check their calendar for hours and availability, as it’s a seasonal offering.) Also great for lunch is Gracie’s Luncheonette, which started as a popular food truck and evolved into a diner. Most ingredients are hyper-local, with pastries, breads and desserts made daily. Speaking of which, do not miss the donuts—and make sure to grab a pint of beer from local Suarez Family Brewery.
Speaking of breweries, beer lovers should check out Honey Hollow Brewery, a farm-to-glass brewery in Earlton, NY. Beers are small batch, hand-crafted, and made from ingredients from their own garden and New York State. The tasting room is housed in a pretty drafty barn, but a firepit out back will warm up visitors. (The beer ought to help, too.) Continuing the theme of beer, Crossroads Brewery in Athens is another great brewery in the area. Their tasting room and food menu are pretty great; their veggie burger and Outrage IPA are a perfect match! Both these locations are part of the Catskills Beverage Trail, which boats six breweries and wineries in one county. Another place to grab a drink is the super-nostalgic Mountain Brahaus in Round Top. The German restaurant and beer garden is currently in its third generation of family owners, and by appearances, not much has been updated since then. (And we mean that in a good way.) Its juke box, dance floor, huge fireplace, big tables and live music make it a popular choice with locals and visitors alike.
Last, dinner options around Oak Hill are a bit more spread out, but also great. We had a great dinner at the Palmer House Cafe, which is housed in a historic home turned restaurant. In the front, the cafe side is charming, with its plentiful tables and dim lighting; in the back, the tavern offers a more lively atmosphere. The two spaces offer the same menu, which changes weekly, and always has veggie and GF options. The Palmer House is located 20-ish minutes away in Rensselaerville NY; if you make it over, check out the beautiful waterfall in town. A bit closer to The DeWitt Oak Hill is Ruby’s Hotel, where the menu changes so often it’s presented on a dry-erase board. The restaurant and bar is housed in an 1800’s architectural gem—inside, the space furnished with all the original tables, chairs, lighting fixtures, Art Deco Bar and soda fountain. Say hello to the owner, Frank, and ask to take a peek at the art gallery upstairs if its open.