If you live in New York City, it’s necessary to escape it every now and then. Earlier this month, I had a couple of days off work and decided to take myself on a trip.
I picked Kingston because I’d read it was historic and cute, plus I found a beautiful apartment above a gallery on Airbnb, which looked ideal for all the reading and writing I had planned.
It ended up being just what I needed – it was quiet and colorful, I found a couple of great places to eat and drink, and I finally got to all the work I find a way to put off when I’m lazing around Brooklyn. But it did have its downsides – such as the weather, the struggle of getting around town and the complete lack of other people…


Thinking of a visit? Here are a few pointers.
What’s the history of Kingston, NY?
The city was settled by the Dutch in 1651 and became the state’s capital in 1777 after Albany – the planned capital – was believed to be under threat from the British. But troops ended up attacking Kingston instead and it was burned to the ground later that year. Luckily, its residents had expected the battle so escaped in time, but the city still commemorates the burning by staging a reenactment every other year.
Its position on the Hudson River allowed it to become a key transportation hub for the area and in 1872, it officially became a city after merging with Roundout, which is right by the water. (If I’m honest — and no offense, Kingston — it feels far more like a town than a city.)

Why visit?
It’s a quiet, historic town on the Hudson River with a smattering of great restaurants, shops, museums, churches and street art. It’s just two hours north of the city and close to other attractive spots in the Catskills, including New Paltz (15 miles south), Minnewaska State Park (25 miles southwest) and Phoenicia (25 miles northwest).

What’s there to do?
The town has two sections. The more central area, the Stockade district, is lined with colorful storefronts, churches and really beautiful, snuggly-looking homes. One such home is the Van Steenburgh House – the only structure not burned down by the British.
If you walk about 20 minutes down to the water, you reach a smaller historic area called the Roundout district next to the Kingston City Marina.
Down here is the Trolley Museum of New York, the Hudson River Maritime Museum and the Rondout Lighthouse – one of only seven left on the Hudson.

In the summer, there are also guided kayaking tours and Hudson River Cruises. (I was narked that I wasn’t there for the right time of year for these.)
The whole place is also awash with art galleries (see list here), including the one I stayed at, The Storefront Gallery.

How do you get there?
I was surprised that it’s not on the train line, but it’s easily accessible by Trailways buses from Port Authority. It takes two hours, costs $25 each way and I didn’t need to book ahead. Alternatively, it’s a two hour drive north, right up I-87.


My thoughts?
When I first got off the bus and started walking around the town, I was immediately glad I’d picked it – the buildings were so cute. But I soon realized it was a terrible time of year to go. There was so much snow on the ground that I felt pretty isolated in the Roundout district and even when I did explore, so many places seemed closed. I was car-less, and I think the trip would have definitely have been improved by having one – or some sunshine.
I did find some trusty places to eat, including Dolce (a big tasty brunch menu), Savona’s (hearty Italian food) and Grounded (exceptional coffee). Bizarrely, I seemed to be the only person dining out, but no doubt the tables are much busier in the summer.


I took the trip for some quiet time, and Kingston could not have been more perfect for that. It was so still and peaceful, and the apartment was ideal. But if you want a bit more buzz, I’d stop a few miles early and go to New Paltz instead.
(The biggest problem was that, even though I’d partly taken the trip as a throwback to my solo travel trips pre-Ryan, I realized I missed him and Georgia too much to do it again! So after a couple of days away, I was more than happy to head back to the city and this lovely face.)
Now I can’t wait till summer — I’ve been thinking I want to take exactly this kind of a trip over a long weekend (but maybe not Kingston, unless there’s a fun summer event). I haven’t tried Air BnB yet but I got a credit for them a while back and hope it’s still valid.
That pumpkin cake looks AMAZING. And Georgia is gorgeous!
She sure is! I missed her smiley face so much!
What place! It’s a complete ghost town. Even the shop looked empty! Sometimes being away puts everything in perspective.
Yeah there’s definitely a right and a wrong time to go. It was pretty isolating and soon after I arrived I was like, ‘I wonder what’s happening in NYC?’ (And I was desperate to get back to the office, obv.)
Sounds so peaceful. I’ve never stayed in Kingston, only passed through it, and it seemed really cute. I’d also suggest Woodstock, NY because that place is just too adorable to miss 🙂
Ooh good tip — maybe this autumn when the leaves turn. That’s always a gorgeous time to head up there 🙂
Shame it was too quiet for you but it does look very pretty.
(I stumbled across this blog via Twitter as I didnt get my usual email for some reason 🙁 )
Wow, you really did have the town all to yourself! Even though it’s deserted, it looks mighty pretty with all that snow! And perfect for the quiet you were looking for!:-)
I’m impressed you went on a solo trip upstate in the thick of winter (ok, almost spring but you’d never guess it)
This looks so cute! I haven’t really done any solo trips upstate, and I’ve been longing to get out of the City for a weekend. When it warms up, this might be a nice option as I grew up in a small town with little places like the ones you described. Thanks for the tip!