And North’s Guide to Autumn Upstate
As the scorching heat of summer recedes to crisp autumn, my thoughts always turn to travel—and, with it, food. For the past 11 years I have run the travel site And North, offering curated recommendations on where to eat, shop, stay, and explore in the regions north of New York City. My travels have taken me all over the Hudson Valley, Catskills, and beyond, and I have been lucky enough to visit countless independent businesses that make this region so rich and unique—delicious too.
If you’re like me, planning a trip around a good meal just makes sense. It offers a delicious destination on which to build the rest of an itinerary, and upstate NY is an embarrassment of riches when it comes to dining. From roadside favorites to James Beard Award–nominated restaurants, I’ve compiled a list of four favorite eateries to visit, paired with selected itineraries for the surrounding area. So grab your favorite sweaters and plan to travel north this fall for delicious fare and aimless autumn drives.
STISSING HOUSE
Located in Pine Plains, NY, Stissing House has quickly become one of the most sought-after food destinations in all of upstate. Run by James Beard Award nominee Clare De Boer, this colonial tavern, dating back to 1783, features wood-fired seasonal meals in the coziest of settings. Simplicity at its very best, the menu highlights flavorful staples like wood-roasted Snowdance Farm chicken, elegantly presented bread and butter, and coal-roasted dayboat scallops with green garlic butter (a personal favorite). On a chilly fall evening, I recommend sitting in their candlelit tavern, sipping on a Pine Plains Martini made with in-house vermouth, and watching the chefs prepare your meal in the wood-burning oven.
Local Itinerary
Like any good upstate destination, expect to drive from town to town to experience the best of the area and to take in the autumn scenery. We recommend visiting Millerton, Wassaic, and Kent, CT, for an aimless day of shopping and exploring.
Shop: Millerton Antique Center, Montage Antiques, Harney & Sons Tea House
Explore: Wethersfield Estate and Garden, Kent Falls State Park
Visit: Tenmile Distillery, Four Brothers Drive-In Movie Theater
DEER MOUNTAIN INN
Set in a historic Arts & Crafts–style hotel dating back to 1880, Deer Mountain Inn is a longtime favorite destination of mine, boasting handsome interiors, expansive mountain views, and some of the area’s best food. Run by Chef Corwin Kave, the restaurant is open seven days a week, offering expertly executed dishes like steelhead trout with sunflower curry, Wagyu bavette with a corn & bean salad, and a crusty sourdough focaccia with various accoutrements. Whether you choose to sit in the main dining room overlooking the autumnal mountainscape, in the cozy darkly lit bar, or by the crackling stone fireplace, Deer Mountain Inn is a special setting you’ll want to return to again and again.
Local Itinerary
Situated near Hunter Mountain and Windham Mountain Club, the Tannersville area is known for its outdoor activities as well as the historic Arts & Crafts mansions once associated with Onteora, one of America’s oldest summer colonies.
Explore: Mountain Top Arboretum, Kaaterskill Falls, North-South Lake
Eat: Matilda at The Henson, Mama’s Boy Burgers, See & Be Kitchen
CASA SUSANNA
Run by James Beard semi-finalist Chef Efrén Hernández, Casa Susanna specializes in modern Mexican cuisine, celebrating the chef’s Jaliscan heritage and the abundance of Hudson Valley ingredients. Set on the grounds of Camptown Catskills, a 50-room boutique hotel, Casa Susanna is set apart by its inventive cuisine and striking interiors. For the ideal people-watching perch, I recommend sitting in the wood-clad bar. It’s ideal for enjoying a classic margarita or two, and ordering the house-made masa and as many vegetable sides as your stomach and wallet will allow. Last time I visited, I couldn’t get over the duck leg confit with heirloom yellow corn and fermented mole negro.
Local Itinerary
Casa Susanna is located in Leeds, which is a perfect jumping off point for a day of exploring the nearby towns of Hudson and Catskill.
Shop: Red Chair on Warren, Colonia Antiques, The Modern Exchange
Explore: Hudson Ferry Co., Thomas Cole House, Olana
Eat: Feast & Floret, Rivertown Lodge, Talbott & Arding
BOVINA FARM & FERMENTORY
Set on a 20-acre homestead in the bucolic rolling hills of the western Catskills, Bovina Farm & Fermentory features Saturday night suppers and charming accommodations. Run by couple Elizabeth Starks and Jake Sackett, the Fermentory is like something out of a dream: small-batch beer is crafted in the timber-frame barn while sheep and ducks roam the property overlooking views of a nearby cow pasture. Sign up in advance for one of their in-demand dinners, a family-style feast paired with house-made drinks. Designed to highlight the season’s best from nearby farms and purveyors, expect the menu to offer inventive takes on classics such as garlic confit with fresh goat cheese, roast pheasant with bitter salad, and salted chocolate cream tart. A meal at the Fermentory feels like you’ve been graciously invited into someone’s home for the evening: Every detail is somehow both highly curated and without pretension. After dinner, wander the property while the fall moon rises, and breathe in the fresh mountain air.
Local Itinerary
This area of the Catskills can resemble the Swiss Alps, with vast farmland set against the backdrop of the mountain range. Aimless drives are the best way to experience the majesty of this region, with some memorable stops along the way.
Shop: Kabinett & Kammer, First Bloom Corner Store, Hobart Book Village
Explore: Putt Putt Van Winkle, Bloomville Rail Trail
Eat: Blue Bee Cafe, Wayside Cider, Magpies on Pink Street
