A Day at New York’s Most Exclusive Members-Only Club, Silo Ridge

• Silo Ridge is a luxurious gated community and private club in a rural area north of New York City.
• Members like Weight Watchers CEO Mindy Grossman enjoy perks from swanky stables to gourmet meals.
• We spent the day at Silo Ridge to see what life is really like for the rarefied residents. 
• See more stories on Insider’s business page.

Whoever said Disneyland was the happiest place on Earth has never been to Silo Ridge

The private gated community and golf course with a laundry list of over-the-top amenities is a two-hour drive north of Manhattan. Its 245 homes are set on 850 lush acres near the quaint town of Amenia, New York, with postcard-worthy valleys and mountains.

Anyone who buys property at Silo Ridge, where prices start at $2.7 million, automatically becomes a club member. Members pay an additional one-time initiation fee of $150,000 and $30,000 in annual membership dues to become a part of the rarefied community.

Opened in 2015, Silo Ridge is just one of real-estate mogul Mike Meldman’s 25 resort-style communities in locations including Tennessee, Barbuda, and Portugal. Their steep price and exclusivity leads to A-list residents and guests from Michael Jordan to Reese Witherspoon to Bill Gates.

The 110 member families at Silo Ridge include celebrities, pro athletes, healthcare executives, and business leaders. Current residents include Weight Watchers CEO Mindy Grossman — who told Insider that “Silo is a gift” (because those in the know drop the “Ridge,” of course) — while NFL star Tom Brady and his model wife Gisele Bündchen used to live there.

Behind the property’s red-brick gates and posted security guards is the epitome of luxury country living — something akin to an adult summer camp.

From an equestrian center to a baseball field modeled after the iconic pitch in “Field of Dreams” to full bars at every “comfort station” (after all, Meldman is a cofounder of Casamigos tequila with George Clooney), the trappings of Silo Ridge cater to and coddle the 1%. 

For some, a home at Silo Ridge is a weekend or vacation destination, with upstate perks from sporting clays shooting and fly fishing to kayaking and axe-throwing.

But Meldman has tapped into the desire of America’s wealthiest people to live like they’re on vacation all year long. And that only deepened during the pandemic, when remote work enabled full-time residence in what were once weekend or seasonal scenic getaways. More residents have made their Silo Ridge property their primary home.

We spent a day at Silo Ridge to see what it’s really like.

Behind the gates, a network of roads winds into the far corners of the community’s vast acreage. Residents drive around on golf carts, even if they’re not planning to hit the green, noshing and imbibing at snack-filled “comfort stations” on the way. (More on those later: Imagine the fanciest bodega with booze and candy to order — and it’s all free.)

Members congregate for gourmet meals, drinks, and activities at two central structures: the Ridge House and the Barn.

I started my day at the Ridge House, where coffee and breakfast were served overlooking the most luscious valley I’ve ever seen. The bar, though doling out coffee, pastries, and breakfast burritos early in the day, was already fully stocked with alcohol. 

Dinner at the Barn will run you a bill like at any typical restaurant, but members enjoy the spoils of Silo’s appropriately named comfort stations, running in to grab savories, sweets, or cocktails whenever they like — all included.

These stations are quaint barn-like cottages located near the property’s silos and central lake; they open up to reveal walls of candies and beverages. Residents can pop in from the green for a snack or a drink — any treat, from Swedish fish to a margarita (Casamigos, of course), can be procured in seconds or minutes.

Silo Ridge’s 245 homes, from two-bedroom condominiums to single-family estates, evoke farmhouses and are nestled into a hilly landscape dotted with lakes.

But before going inside one, I took a golf-cart tour of the grounds, which traced the pristine 18-hole stretch designed by famed golf-course architect Tom Fazio.

Silo employs 165 staff, a number that includes both full-time and seasonal workers. They serve the 110 member families. It’s not only immediate family but also parents, grandparents, and pets who are welcome on the grounds.

I grabbed a Hershey bar from a comfort station and admired the view from its porch before it was back in the driver’s seat of my cart.

From there, my guide directed me to the 3-acre organic garden, where residents can plant and harvest their own produce. 

It’s neighbored by a hydroponic greenhouse and chicken coops, where, as I arrived, a little boy and his father had just made their way from collecting some fresh morning eggs.

Animal friends are aplenty, too, with a set of giant Flemish rabbits and three miniature goats — including the very friendly Lola the LaMancha — hovering nearby, ready to interact with kids.

Soon after it was time for lunch at the Barn, where the salmon and sweet potatoes were better than any dish I’ve enjoyed at a restaurant in Manhattan.

A massive structure, the Barn is an 11,000-square-foot family center that, aside from its restaurant and bar, offers members use of facilities from a vintage arcade and movie theater to a bowling alley and candy station. 

Members were scattered throughout as I passed through. Two smiling parents and their young son enjoyed bowling downstairs while a father and son laughed over ping-pong on the back deck, from which I could see a handful of kids at the edge of the lake, bouncing on an inflatable water trampoline. 

The Barn’s picturesque views were as delicious as the salmon, overlooking Silo’s central lake and mountain ridges that seem to seal off the property from the rest of the world. 

After lunch I toured the new equestrian center across the road, a beautiful stable home to rows of thoroughbreds.

In true Discovery fashion, even the tack room off the stable is complete with an en-suite bathroom and shower fit for a five-star hotel, with everything from band-aids and Advil to singly-packed Neutrogena makeup-remover wipes stationed neatly in sink-side baskets.

Beside the tack room is a lounge with large glass doors overlooking the stable’s paddocks and meadows. With a fully stocked bar and snack station inside, not to mention a gorgeous stone fireplace and outdoor seating space, the spot serves as a popular observatory for parents who want to watch their children learn to ride. 

And after spending probably too long petting an Appaloosa, two guides drove me further up the mountain in an ATV to The Cabin (nestled just at the edge of the woods) for what they call “outdoor pursuits.”

Silo offers everything from sporting clay and skeet shooting to axe-throwing and archery. To my surprise, I successfully shot about seven clays thanks to some masterful instruction — despite never braving the sport before. 

From there it was back across the tall grass and fields (and past a barn that houses four-wheelers and snowmobiles for wintertime cavorting) to return to the residential side of Silo Ridge, where I toured a home. 

Homes at Silo are built across five on-site neighborhoods, ranging from two- and four-bedroom condos to single-family residences. For the most private of members are estate home sites: custom properties built against a 220-acre forest preserve, where residents can design their dream homes on up to 2 acres of land.

The contemporary four-bedroom home I toured was worth an estimated $7 million, according to my guide. It boasted sky-high ceilings, exposed wood, a stunning back porch, warm, chic finishes (like a barn door), and picturesque views of the lake.

Not to mention an in-home theater, gym, bar, and en-suite bathroom off every bedroom.

I made my way through a hidden path near the house to discover a cliff jump, where members can dive into a 40-foot-deep lake at the top of a hiking trail if they feel like a swim.

Passing plenty of quiet sitting spots and hammocks for golfers, kids, friends, and families, I then found myself on the green meeting a quartet of Silo golfers, four fathers wrapping up a game, with an attendant serving Casamigos tequila from a cart nearby. 

By the end of the afternoon, I found myself at another comfort station, this time winding down the day with friendly staff and residents, drinking margaritas from a quaint porch with views of Silo’s pastures, estates, and hills.

Overlooking the idyllic vistas bathed in early evening light, I could see the allure of a community like Silo Ridge, especially during the pandemic. Space. Peace. Every comfort. Built-in friends. A dedicated staff.

Wouldn’t it be grand if we were all on vacation all the time?