weekend escape: kingston, ny

One of many public artworks in Kingston

If I’d listened to my Hudson friends, I might never have checked out Kingston. It’s historically gotten a bit of a bad rap—perhaps because it is really more of a big city than the quaint waterside towns nearby. In fact, Kingston was the original capital of New York! But, like many of these upstate towns, it’s going through a revitalization, with a huge focus on bringing back jobs and affordable housing to the city while keeping the artist vibe alive. The focus on empowering the existing community, instead of leaning into “weekenders,” might be what draws us to this area so much.

The main drag in Kingston’s Stockade District
A snowy night at Rough Draft – bar / bookstore in the Stockade

Kingston is a sprawling city, but the two main areas that out of towners like us tend to spend time is uptown in the historic Stockade District (with buildings from the 17th century.. that were burned by the British during the Revolutionary War!) and the downtown Roundout waterfront. Both of these areas are filled with shops, bars and restaurants that resemble the smaller main streets of the other towns nearby.



The main street in the Rondout area

But, because Kingston is more populated, these areas tend to be a bit more trafficked year round (that’s something we like!). And, because it’s a relatively cheaper area, there are more new places popping up that keep the areas feeling fresh.

Everyone enjoying some vintage shopping

Quickly, Kingston has become one of our favorite places to hang out (and keep on our Zillow alerts). We have our routine spots during quick trips (lunch at Outdated, a cafe/antique store, vintage shopping uptown and downtown, and drinks at Rough Draft, a book store/bar), and we’ve also enjoyed many afternoons at the Hutton Brickyards, an old brick manufacturer turned outdoor event space that hosts music events and food/flea markets like Smorgasburg and Renegade.

At a flea market in the Hutton Brickyards

The area is vibrant enough not to feel eerily quiet at off times of year, but parking is always easy to find. And, when we were recently trying to find a big art piece for our new apartment, we even had the small town pleasure of being adopted by a few local artists who took us around town to various galleries and closed-to-the-public hubs (even one of their homes!) to view the works of one of their beloved artist friends. (Plus, we could even afford the art! And it was auctioned off to create a scholarship for other artists in the area.) I can’t say we’ve had that experience in any other towns around here.

More drinks at Rough Draft

Stay: If you can find it, an Airbnb in the uptown Stockade area or waterfront Roundout area is great for walkability to shops, bars and restaurants. More often, though, we tend to find an Airbnb ~15 minutes away (usually enroute to Woodstock or Saugerties area) that is a bit nicer and gives us more outdoor space.


  • Brunette – the (natural!) wine bar you’ve probably seen on Instagram
  • Rough Draft – my favorite place on earth? or just another book store slash bar (also has coffee and bagels!)
  • Stockade Tavern – a more upscale cocktail bar in a cozy setting


  • Wilde Beest– an upscale but cozy and unpretentious ‘garden to table’ spot
  • Outdated – our favorite breakfast/lunch spot (also a vintage store!)
  • Boitsons – a cozy pub enviroment with an oudoor patio
  • Sissy’s – lots of choices for breakfast or lunch, if Outdated is too crowded

Do: Hit up both the Stockade area and the Roundout areas for shopping (and meals, too). Naturally, I gravitate towards the vintage and local maker shops, of which there are many. There are also numerous art galleries throughout the city, and special events like First Saturday and the O+ festival. Check if there are any flea markets/music shows going on at the Hutton Brickyards. Also, Kingston’s Saturday farmer’s market is one of the biggest in the area, and happens inside or outdoors most of the year (find out more here).


Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s