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Upstate Dreams: A Last-Minute Getaway to Millbrook, New York

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Though Millbrook is only a quick train ride from New York City, the town feels lightyears away from the hectic pace of Manhattan and is an ideal getaway for the urban explorer. If you prefer an equestrian lifestyle and aesthetic to the surfer and socialite havens out east in Montauk, then you’re in luck. When the private helicopter company, Blade, first began marketing their flights to Millbrook, they deemed the destination “the unHamptons” and described its clientele as the “year-round weekend native.” Many devotees rolled their eyes—publicity is not what they’re after. 

But with the popularity of the polo matches, and the general desire to leave Manhattan on weekends, Millbrook has seen a rise in popularity. And there are plenty of ways to enjoy the bucolic landscape of the region — from thrifting to fishing to wine-tasting, and more. Though Millbrook is wonderful to visit year-round, summertime is best for outdoor exploration in the Hudson Valley. Whether you’re interested in hiking and canoeing, picnics or polo, we’ve got you covered. Here’s your guide to a last-minute long weekend in Millbrook, New York.

Retro Diners & Drive-In Theaters

Drive In Theatre

(Image of drive-in theatre provided by Adobe Stock)

When you’re out of the concrete jungle, you may as well reap the fruits of your surrounding nature (literally). Head to the Millbrook Farmers Market for an array of breakfast treats—our hostess was a crowd-pleaser by waking us up every morning with powdered donuts. The Millbrook Diner is the go-to spot both for the struggling hungover masses, and for the people-watchers (the latter certainly a nightmare for the former): the greasy food is sublime and Blake Lively has been spotted there in the past. The retro diner is a Millbrook institution. Visitors will earn bonus points if they can figure out why the jukeboxes at every seat don’t work. 

For another old-school delight, head to the Four Brothers Drive-In Theater — the gorgeous, pastoral landscape is a jarring counterpoint occasionally to what is onscreen. Request the boombox stereo to accompany your own radio device: it’s free, and the sound is not very good. (Fortunately, the pizza is.) Gorgeous lighting, inventive cuisine, and an attentive chef makes Serevan a highly recommended option for a date night. (Order the beef stew.) The owner at Stissing House used to own the restaurant, Provence, in New York City. The rustic vibe indoors reflects its woodsy surroundings, and is a popular choice for an evening out on the town. 

Finally, head over to Millbrook Vineyards & Winery to sample the local flavor. Hailed by The New York Times as "the Hudson Valley's flagship winery,” this bucolic 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. Cheers!

Blue Jean Balls & Polo Matches

Polo Match

(Image of Polo match provided by Adobe Stock)

Travelers in the summer months should check to see which events are being held on the weekends. The Fitch’s Corner Horse Trials Weekend & Blue Jean Ball is an annual summertime event that features horse trials at Fitch’s Corner, with dressage, cross-country, and stadium jumping for horses from around the world. Be sure to buy a ticket for the Blue Jean Ball in the evening, an annual tradition going back twenty-plus years. The event includes 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 evergreen requirement.

Check out the summer schedule for the Mashomack Polo Club, which welcomes visitors during the warmer months — and it’s free to attend. Opening weekend is Memorial Day, and the revelry (and horsemanship) continues through the end of the season. Head over to Orvis Sandanona to experience shooting grounds suitable for all levels, with an array of different courses to try. Want to get away? Head out of town to Stissing Mountain, which is located about thirty minutes away from Millbrook, to explore the gorgeous trails. And, if you’re visiting in the winter months, head over to Catamount Mountain. Perhaps unsurprisingly, this, too, caters towards the old-school. Snowboarders can be heard grumbling about the steep chairlifts, as they never have time to get their footing on the board before being dropped down through the air. In Millbrook, old-school pursuits always win — so, we suggest you go native.

Country Houses & Antiques

Antique Store

(Image of antique store provided by Adobe Stock)

In the mood to shop? Head to Alicia Adams Alpaca, a luxury boutique in town. Punch is the punchiest (pun intended, apologies) mix of well-priced uniform necessities and equestrian and quirky accessories, clothing and décor. But the main event truly is antiquing in either Millbrook or Millerton, which is a treasure trove for unexpected yet elegant finds. As for where to stay, we suggest the Millbrook Inn, which was originally a school established in 1906, it opened as an inn in 2011. Additionally, the Millbrook Country House offers quaint coziness, with a tiny B&B. If you’d prefer not to interact with your host, there are additional options in nearby Wassaic, and a variety of rentals in Millbrook, including waterfront Victorian estates, as well. 

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