Fall is the perfect time to visit Millbrook, and this Hudson Valley haven for shooting, riding, fishing, and socializing has never been more popular. A surefire sign of the town’s rise in visibility occurred this past April when Blade announced it would be adding Millbrook to its roster of destinations—joining such locales as Nantucket, the Hamptons, and LA. Millbrook devotees rolled their eyes at Blade’s marketing of Millbrook as “the unHamptons,” referencing its clientele as the “year-round weekend native.” In Millbrook, publicity is not what they’re after.
But the growing demand for less-populated city escapes, combined with the rising stature of Millbrook’s polo matches and annual events, means that this upstate town is here to stay. Since there is a heavy dinner-party scene, the best way to see Millbrook is often to stay with a native. But, in lieu of that, the bucolic landscape is enough to make the trip north, and there is plenty to do—for both the nature-lover and the party-enthusiast.
PUT ‘EM BACK
Millbrook Vineyards & Winery // 26 Wing Rd, Millbrook, NY 12545
Hailed by The New York Times as "the Hudson Valley's flagship winery,” this vineyard is the perfect afternoon escape all year round. Head up to the second floor for a wine tasting around a large wooden bar and talk about the local grapes with the knowledgeable (and generous) servers.
The Hunt Ball
Millbrook is known for mixing black-tie glamour with the rugged tradition of hunting and riding (and beagling and basseting)—it’s all very English country weekend. The Hunt Ball, hosted by the Millbrook Hunt during the holiday season, carries out an old British tradition and the proceeds, naturally, go to the dogs (and the trails, etc.) The ‘Meet’ for the Hunt changes every time, and is hosted at different private farms, but the place where they do meet is called a ‘Fixture’—so you know the correct lingo if you ever plan to join.
Fitch’s Corner Horse Trials Weekend & Blue Jean Ball // North Mabbettsville Road, Millbrook, NY 12545
The horse trials weekend at Fitch’s Corner showcases horses from around the world, and is capped off in the evening by the Blue Jean Ball, a 20-plus year Millbrook tradition. The ball consists of dinner and dancing, and an imaginative dress code: past themes include Van Gogh’s Starry Night and Rio Nights, but, of course, denim is an annual requirement.
IF YOU CAN GET IN
Mashomack Preserve Club // 7435 NY-82, Pine Plains, NY 12567
Though Mashomack is a private fish and game club, the polo fields are open to the public during the summer, drawing both a local and international crowd. Memorial Day opening weekend kicks off a months-long series of events, with the Stissing Cup in early June to the Smithfield/Shekomeko Open in late September.
Tamarack Preserve Ltd // 4754 US-44, Amenia, NY 12501
A mecca for hunting and fishing in Millbrook, Tamarack is a rustic and relaxed club featuring a five-star restaurant. Whether dining outside overlooking the golf course, or beneath the feathered and antlered taxidermy in the Grille Room—what a beautiful room of death—stick to the classics: the Bloody Mary and the burger can’t be beat.
The Millbrook Golf & Tennis Club // 103 NY-343, Millbrook, NY 12545
Last but not least: racquet sports. The G&T appeals to those with less murderous tendencies in their leisure pursuits (or, at the very least, those who prefer club trophies to animal skulls). The paddle tennis, or “platform tennis,” provides ample social opportunities for winter weekend tournaments.
Seravan // 6 Autumn Ln, Amenia, NY 12501
Gorgeous lighting, inventive cuisine, and an attentive chef: a perfect choice for a date night. One recommendation? Get the beef stew.
The Stissing House // 7801 South Main Street, Pine Plains, New York 12567
A rustic setting perfect for a cool fall or winter night. The owners, Michel and Patricia Jean, used to own Provence in New York City, before taking their talent upstate.
GET YOUR FIX
Millbrook Farmers Market // 3263 Franklin Ave, Millbrook, NY 12545
When you’re out of the concrete jungle, you may as well reap the fruits of your surrounding nature. Head to the market for breakfast treats, including powdered donuts.
Millbrook Diner // 3266 Franklin Ave, Millbrook, NY 12545
The Millbrook Diner is the go-to spot for both the struggling hungover masses, and the people-watchers (Blake Lively is said to have been spotted there recently). The retro diner and its greasy food is a Millbrook institution. Bonus points if you can figure out why the juke boxes at every seat don’t work.
Four Brothers Drive In Theatre // 4957 NY-22, Amenia, NY 12501
Highly recommended for an evening in the summer or early fall. The crickets chirping and fireflies lighting up the trees provide a gorgeous framework for whatever’s happening onscreen—which, in the case of an October showing, was the burned-out apocalypse of Blade Runner 2049. Word to the wise: request the boom box to accompany your car stereo: it’s free, and the sound in the field is not the best. Fortunately, the pizza is.
Orvis Sandanona // 3047 Sharon Turnpike, Millbrook, NY 12545
Head over to the Orvis Sandanona to experience the shooting ground ranked among the best in the country, and perfect for a day of sporting clays or fly fishing. The shotgun course is perfect for all levels (and features very patient guides). The lunch (and wine) afterwards is well-worth the entire endeavor, and the shop inside is heaven for all fishing and shooting enthusiasts—and those who like to dress like they are.
OFF THE GRID
Stissing Mountain // Stissing Mountain Dr, Pine Plains, NY 12657
Stissing Mountain, located about 30 minutes away from Millbrook, offers a variety of hikes for the day-tripper. The mountain is best to visit in the fall, when the leaves are changing.
Catamount Ski Area // 78 Catamount Rd, Hillsdale, NY 12529
For winter visitors, Catamount is located only 45 minutes from Millbrook, though this resort caters towards the old-school: snowboarders complain that the steep chairlifts don’t allow enough time to get their footing on the board. Maybe they should switch to skis?
FILL YOUR BAG
Punch // 15 Merrit Ave, Millbrook, NY 12545
This shop is filled with equestrian décor and apparel (hint: get something for your girlfriend). Antiquing in Millbrook and nearby Millerton is renowned, so check it out when in town to assess the paintings of dogs and portraits of scowling ancestors (not your own).
Alicia Adams Alpaca // 3262 Franklin Ave, Millbrook, NY 12545
This boutique is all alpaca all the time: capes, blankets, socks, sweaters, anything you can imagine. The wool is outrageously soft (and accordingly priced), but the store is well worth a visit.
HANG YOUR HAT
The Millbrook Inn // 3 Gifford Road Millbrook, NY 12545
Originally established in 1906 as a school, the Millbrook Inn opened as a hotel in 2011. Rent a room and pretend you own your own historic Hudson Valley estate. Or you can go stay nearby in hipster Wassaic: the choice is yours.
Special thanks to Adam Brenner, Emily Hottenson and Rebecca Regan for the insider tips!