Jon Makhmaltchi of J.Mak's Rhinebeck, New York

© Robert Rodriguez Jr. //

Travel adviser J.Mak shares his favorite places to eat, drink, and stay in Rhinebeck, New York—from where to find the perfect nightcap, the most spectacular views, the best steak au poivre, and more.

When J.Mak isn't scouring the globe to advise discerning travelers about how to best experience the finest hotel properties around the world—think: Sorrel River Ranch, J.K. Capri, and Post Ranch Inn, among them—there's no place he'd rather be than this charming upstate town. Here, the New York native gives the 411 on his favorite escape.

What neighborhood are you from, and how long did/have you live there? How often do you go back? I am a native Manhattanite, born and raised on the Upper West Side. I love NYC—it’s my favorite island destination—but, I love escaping and heading to my country home in Rhinebeck in the Hudson Valley more than anything. It’s where I can actually exhale and relax. It’s far enough away that it’s a true escape, and yet so easy to get to. It’s an unassuming town that’s filled with creative and amazing people like Annie Leibovitz, Paul Rudd, Eric Roberts, and more.

Where would you put up friends visiting town? When people visit us in Rhinebeck, I set them up at my favorite historic hotel, The Rhinecliff Hotel. It’s country chic and comfortable and just down the street from us. We even got married there! (4 Grinnell St.; 845-876-0590;

Where is the best place to find your hometown’s signature dish? Gigi’s has this awesome dish called the skizza—their take on a thin and crispy pizza. There’s nowhere else to find it and it’s super tasty! (6422 Montgomery St.; 845-876-1007;

What is your favorite restaurant to take visitors? Market Street. Luciano is the GM and treats us like royals. You will see all the local celebs there (including me!) (19 W. Market St.; 845-876-7200;

Where can you find the best cocktails? Beer list? Wine list? Grand Cru Beer & Cheese Market in Rhinebeck is my afternoon retreat and guilty pleasure. I love to sample their array of cheeses and extraordinary beers (many of them from the local brewing industry). Wine and small plates are options, too. And, let’s be honest, I sample them all! (6384 Mill St.; 845-876-6992;

Where would you choose to splurge on a night out? Le Petit Bistro in town. It has the best steak au poivre ever, the house salad is to die for, and they have an amazing wine list (8 E. Market St.; 845-876-7400;

What is your go-to after-hours bar? Rhinebeck and I are soul mates; we both shut down early! I do love a nightcap at the old bar inside the Beekman Arms Inn. It’s old, it’s cozy, and it has a fireplace (6387 Mill St.; 845-876-7077;

What’s the best way to spend a Saturday afternoon in town? I love taking a scenic water tour in from Rhinecliff Dock to Kingston Point Park across the Hudson. We have a kayak launch, which makes crossing the Hudson a breeze, and I love meandering through the natural canals. There is really nothing else like exploring the area from the water!

What is your Sunday morning routine in your neighborhood? We usually head to the Sunday Rhinebeck farmers’ market. We’ll ride our bikes and fill up on the local fruits and vegetables from the area, and we get to catch up with all our local pals too! (61 E. Market St.;

Where is the best brunch? Market Street in Rhinebeck is the best. I love it there, and I totally love their ginger margarita on the rocks with salt, the kale salad, rigatoni, and the salted caramel budino! Tell the GM, Luciano, that I sent you!

Where do you go for the perfect cup of coffee? I go to Bread Alone basically every morning when I’m in Rhinebeck. It’s the town’s hub. I always order a vanilla latte and wheat bagel toasted with cream cheese and tomato (45 E. Market St.; 845-876-3108;

What’s your favorite view in town (that tourists might not know about)? Rhinebeck is on the main artery line of Amtrak—probably the most scenic train ride in America. Riding the train to Rhinebeck is like being taken back in time to the time of the great New York families—the Astors, the Vanderbilts—and the entire way up along the Hudson River is studded with castles and bridges. It’s breathtaking. (You have to sit on the left side of the train to get the view). Getting there is really part of the experience. It’s very rustic and yet sophisticated. People from around the world find a sense of peace here, something that makes you feel good. I think it’s the simplicity of it.

What’s your favorite path or trail to follow on a walk? Winter or summer, I love walking down Red Hook's Poet’s Walk, named in honor of Washington Irving and other literary giants who may have walked its paths. Poet’s Walk is rumored to be the inspiration behind Irving's Rip Van Winkle(River Rd.; 845-473-4440;

What are your favorite offbeat cultural attractions? Climbing the towers at Ferncliff Forest. It’s an old growth forest and nature preserve, which has had several towers—one of which served as a look out point for planes which might have approached President Franklin Roosevelt's home in nearby Hyde Park during WWII. The present tower dates from 2007 and offers great views of the Hudson River and Catskill Mountains (68 Mt. Rutsen Rd.; 845-876-1559;

What’s your favorite shop or boutique? There are a lot of specialty shops in Rhinebeck. There are no chains. Going to A.J. Stickles is a must! It’s like an old school five & dime, and they sell everything (13 E. Market St.).

What’s the ultimate souvenir from your town—something you can only get there? The must-have is absolutely wool. There’s actually a sheep & wool festival! (October 17 and 18; 6550 Spring Brook Ave.;

What’s the best-kept local secret? The area as a whole. It doesn’t get the same attention that the Hamptons gets, which is exactly why we love it so much. Hourly Amtrak Empire Service makes the trip so special, with scenic Hudson Valley views and landmarks like the bridges, West Point, Bannerman Castle, and more. It’s really about the Amtrak though, it’s much more sophisticated than the LIRR or Metro North—we have business class, Wi-Fi, and bar cars on some morning trains. 

In our Hometown Guides series, we're seeking the best restaurants, bars, vistas, and things to do in a given place from the people who know best—the artists, designers, chefs, and store-owners who live there. See more Hometown Guides »

Photo Credits: Courtesy of Grand Cru; © Natalie Chitwood /