Kinderhook by Candlelight
Kinderhook, NY
Fri. Dec 5 - Sat. Dec 6, 2025
It’s properly post-Thanksgiving and it’s time to get serious about holiday jaunts.
Spend your first December weekend in one of the most historic villages in New York: ensconce yourself in an immaculately revivified 1800s inn, enjoy small plates of large culinary ambition, and turn out with the rest of town to ring in the holiday season by candlelight.
As always, it’s all already reserved, ready to book in a click.
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Why here?
First settled in the 1670s, Kinderhook is one of the oldest villages in the state of New York.
It’s quintessential territory for The Overnightist: as quaint as you want your holiday village to be, but none of it feels manufactured. There’s rich local lore, interesting quirks and a deep community memory that spans four centuries; the place has served as landing-spot for Henry Hudson, as birthplace to a president, and as literary inspiration to one of the most famous works in American literature. And the story goes on.
This weekend is a rare Friday getaway for us (we tend to build our overnights around Saturday stays), but there’s a good reason. Friday is Candlelight Night, Kinderhook’s annual holiday celebration. It’s full of lights and music, boasts a holiday market and local shopping, and most importantly, carries an authentic sense of tradition and celebration. And your lodging for the night — at the beautiful and contemplatively restored Old Dutch Inn — quite literally overlooks the bustle of it all.
Kinderhook is history-filled of course, but very much alive with its own contemporary energy. And luckily, the village supplies a hotel that embodies that past and progress in microcosm.
So skirt up the east coast of the Hudson, 130 miles north of New York City and 400 years through time, to a town that’s honoring its past by building its future.
This weekend in Kinderhook, discover…
The stay.
Old Dutch Inn
Old Dutch Inn sits at the geographic heart of Kinderhook, and it’s a centerpoint of its history too. Dating to the 1820s, the building has served as a residence, a shoe shop, a community hall, and several stints as a hotel. But this current incarnation maybe be its ideal form.
The property’s owner and restorer, Jennifer Ose-MacDonald, has found an artful balance between preservation and modern amenities. And she’s no interloping NYC hotelier; she’s part of family that goes back generations in Kinderhook.
”I didn’t want to only know my town after work hours,” she told The Overnightist. “I wanted to be part of all of its moments, experience its stages, and get to know all of its personalities.”
So get to know this era of the hotel by holing up in one of the inn’s gorgeous third floor suites — in the very space, where, in another stage, Kinderhook citizens assembled to rally volunteers for the Union army in 1861.
But it’s not all history.
”I was clear from the outset that I wasn’t going to build a museum,” says Ose-MacDonald. “I reimagined it as a place designed for contemporary travel standards that still honored its history and one which helped to establish the larger community ‘space’ it existed in.”
What’s the owner’s favorite nook?
“I absolutely love our reading library. It consists of two built-in bookshelves that we added during our renovations which flank a decorative brick fireplace,” she says. “I also like to think I already have every book ever written about Kinderhook.”
The House of History, Village Square, and more
Nothing named the House of History will fail to make our overnight suggestions.
Walkable from your hotel is whole square’s worth of history, including the former residence of local luminary James Vanderpoel, the House of History itself, built in 1820.
It’s a standout example of the Federal style, beautifully decorated during the holiday, and it’s only one of a wonderful collection of historic sites dotting the square.
Also nearby are the very likely inspirations for Washington Irving’s The Legend of Sleepy Hollow, and last but certainly not historically-least, the birthplace of a president: Martin Van Buren.
If you should burn out on history, pop over to Kinderhook Knitting Mill, a one of a kind community-led business project set within an 1870s textile mill. There’s food, art and a whole range of unique businesses in the space, which was conceived by restaurateur Yen Ngo and artist Darren Waterston.
The day.
The find.
Kinderhook Books
"Wherever I go, bookstores are still the closest thing to a town square,” goes the Goria Steinem quote on their website.
Here, the books are not just metaphorically close to the town square; they are right on it in fact. Sharing a wall practically with Old Dutch Inn.
Walk out of your hotel, hang a sharp right and check out their specialties including “reading-nook curation, and bookish gifts,” as they put it, nicely.
The food.
Isola
Helmed by owner and wine director Hilary Zio, with a menu crafted by Chef Mikayla Summers, Isola celebrates “the islands and coasts of Europe through low-intervention, small-producer wines and artful, ingredient-driven small plates” says Zio.
Isola is another reimagination in this town. The restaurant lives within a faithfully restored 1787 building, with redesigned interiors by designer Anthony D’Argenzio.
Sustainability is as much as mission as the food:
"Isola is committed to the smallest earth imprint possible—minimizing plastics, choosing petroleum-free materials, and using only environmentally sound pantry, beverage, and to-go 'products,” Zio tells The Overnightist.
In keeping with our village square walkability theme, Isola is just around the corner from your hotel. Reservations are for 7:30 on Friday evening.
OK Pantry
So it’s impossible to nail down a favorite spot in the Knitting Mill (see above), but we’ll point you to OK Pantry.
The word ‘OK’ was immortalized right here in town. (Favorite son Martin Van Buren, during his reelection campaign for president in 1840, asserted that OK stood for ‘Old Kinderhook’).
OK Pantry is not tidily described, but it’s a sort of nouveau general store with gifts, toys, books, fresh fruit, a drink counter, kitchenware, it goes on.
”SMALL TREASURES to gift YOUR SPECIAL PERSON NEIGHBOR FRIEND SISTER LOVER FOE (to turn them to FRIEND STAT),” is a social media post of theirs. You should go.
The tucked away.
The evening mood.
Candlelight Night
The holiday event of the year in Kinderhook. It’s intimate but hugely festive, and the shops and businesses of the village square all get involved in creative ways.
This all unfolds directly in front of your quarters at Old Dutch Inn, which will host its own excellent contributions to the line-up: a spirits bar and a candy bar, among others. There’s no charge for Candlelight Night itself, but we’re including a $75 credit at the bar(s) at the hotel.
Stroll the evening square, have dinner, retire to the inn and find a nook in Jennifer Ose-MacDonald’s incredibly-curated reading library.
This weekend experience Kinderhook, its past and its dynamic present, in full.
One-night stay for two at Old Dutch Inn. Fri. Dec. 5, 2025.
Pre-paid dinner at Isola. You have reservations at 7:30pm on Friday evening.
$75 credit at Old Dutch Inn’s spirits bar (or candy bar?) Friday evening. All taken care of, just show up.
You’ll receive a detailed itinerary after booking confirmation.
Book it all in a click.
This overnight is no longer available. Join our Weekly Weekend newsletter to get new destinations in your inbox every Sunday.
Old Dutch Inn graciously provided accommodations for The Overnightist as part of this weekend.