Sat. March 21 - Sun. March 22 | 2026
Millerton & Dover Plains, NY
Pure Maple, Hudson Valley
A sugar-season weekend escape, short and sweet.
It’s the absolute pinnacle of syrup season, and what you need this weekend is a full-on maple immersion. Here you go:
Included this weekend:
A little sugaring. It’s Maple Weekend at Soukup Farms, a family-run operation that’s been tastily tapping trees since the 1950s.
Stay in a glory of an inn, a centerpiece of Main Street in one of America’s great small towns.
A maple-everything Sunday breakfast, right on on the farm.
As always, your stay, meal and local experience are all bookable in one click.
Get the full story for the weekend.
Where you’re going:
Millerton, NY. Around two hours from NYC.
Why here?
Photo courtesy Soukup Farms
Maple syrup is extremely good.
And honestly it’s pretty good for you, too, at least by things-that-are-sweet standards. We’re not exactly nutritionists here at The Overnightist, but let us generally tout the benefits of good, real, fresh maple syrup, straight from a tree.
It has plenty of antioxidants, a relatively low glycemic index vs. refined sugar, and is rich in zinc and manganese and riboflavin and deliciousness.
It’s still sugar and whatnot, but as you ladle it generously atop everything in sight (as we do), isn’t it nice to know that this stuff has some real virtue to it?
Read on or
Photo credit: Soukup Farms
And now’s the perfect time for maple-based travel.
East coast syrup season runs from mid-February to early April, and we’re smack in the middle of it. Smoke-pluming sugar shacks from New York to New England to Montreal are abuzz.
What’s perfect about Soukup Farms (where you’re going, and which will be in the midst of its annual Maple Weekend) is that it’s just a short drive from your home base in Millerton, NY.
Millerton, situated in the Hudson Valley along the eastern fringe of the New York/Connecticut line, is a fantastic small town. We’re not really listicle people, but it was named one of the 10 coolest towns in America by Frommer’s. The New York Times called it ‘Williamsburg on the Hudson’, and we get where they’re coming from: there are surprisingly well-entrenched arts, literary and culinary scenes in what’s essentially a tiny village. A strong Main Street too, and your hotel’s right on it. All very cool, but a casual kind of cool.
So come for the syrup and stay for the town, or vice versa. Because taps are tapping, the amber is flowing and the maple (which we’ve established is not totally unhealthful) is in its prime.
Photo courtesy the Millerton Inn
This weekend in Millerton, discover…
The stay.
Photo credit: Yannis Malevitis, Millerton Inn
The Millerton Inn
We are suckers for angular little rooms like this.
The Millerton is incredibly intimate, with 11 suites all set in a neat Victorian that dates to the 1860s. Everything has been fully and beautifully restored in recent years.
The inn comes with an excellent Mediterranean restaurant and tap room on-site, and the whole enterprise is the passion project of restauranteur Peter Stefano and his daughter Eleni.
There’s a pleasing expanse of a wrap-around front porch, a warm and woody foyer, and well-appointed rooms throughout. And of course every shop in town is just a short, walkable wander away.
You’re reserved ror Saturday night. Sleeps three.
The day.
Photo courtesy Soukup Farms
Maple Weekend, Soukup Farms
This is not a concocted, tourist-placating farm. This is a real, working, family farm that’s been in the syrup game since the Eisenhower administration.
Maple Weekend is the time visit. As the Soukup family puts it, the event “takes visitors back to their agricultural roots as they learn how a clear, water-like sap becomes a golden brown nectar.”
There will be plenty of nectar. There’s a self-guided maple tour, syrup samples, maple popcorn, maple and apple cider donuts, maple popcorn, and maple syrup making (if the weather cooperates).
No charge for admission here, but there’s syrup galore available for purchase. And a full breakfast (we’ll talk about that).
We’re including a $100 credit to spend on maple things and breakfast on the farm.
Syrup images and color guidance via Barred Woods Maple
The find.
Oblong Books
Just a great, free-thinking, independent bookstore that’s been operating in Millerton for 50 years (Oblong opened a second location in nearby Rhinebeck years back, and the pair of stores are the largest independent booksellers in the Hudson Valley).
Owner Dick Hermans co-founded Oblong in 1975, and balanced the book business with anti-nuclear organizing.
“For two summers,” he remembers, “we lived in a teepee … to save money and rode mopeds the 17 miles to Millerton.”
This Overnight includes a $50 credit to spend in-store.
The food.
Photo via Soukop Farms
Maple Breakfast at the Farm
Back to the farm. We usually go with a local dinner in the food portion of our weekend planning, but breakfast felt right for this one.
A full breakfast menu is available at the farm on Sunday, with maple sugar oatmeal, shortstacks of blueberry pancakes, and maple bacon chili “with a cornbread waffle slice”.
You have a $100 credit to put towards breakfast and anything that grabs you in the farm store.
. That’s maple frosting.
The tucked away.
Harlem Valley Rail Trail
26 miles of mostly-wooded pathway, tracing the route of an abandoned stretch of the old New York & Harlem Railroad corridor.
It’s a wild-feeling glimpse at Hudson Valley splendor, particularly now, with sprigs of spring popping up here and there. The trail courses through wetlands and grasslands, along creeks, and through Christmas tree farms on its way across the countryside.
The rail trail is accessible right off Main Street in Millerton.
The evening mood.
Photo via Willa
Willa
A swanky-but-real-feeling Millerton restaurant and bar that’s perfect for a later-night stop-in. Right next to your hotel, practically.
There’s a nicely curated drinks list (that includes a maple syrup ‘shortstack’ cocktail, for the record), and there’s no skimping on the mocktail options.
Eat too by all means. They serve bites and plates, and Willa’s ingredients are locally sourced via partnerships with local farms:
“Our intention is to responsibly source the food that we cook,” says Willa.”We wish to build relationships with the farmers that grow our vegetables, fruit, herbs and raise our meat… it is our goal to create tasty food that showcases the hard work of these individuals.”
Book it all in a click.
This Overnight includes:
Your stay at the Millerton Inn. Reserved for Saturday, March 21, 2026. Sleeps three.
Full breakfast at Soukop Farm on Sunday morning (between 9:30am and 1:30pm). You’ll have a $100 credit to spend on your meal, plus any manner of maple things in the farm store.
A $50 credit to Oblong Books, right around the corner from your hotel.
See here for a full list of photo credits for this story.