my guide to upstate ny
my favorite spots + how to build the most perfect weekend
this guide has been a loooooong time coming. as you know by now, upstate ny is one of my favorite destinations. I rent a house with friends for my birthday ever year & alex and I love spending a weekend there every few months. this weekend we celebrated our 6 year anniversary & had the loveliest time :’)
life goal is to own my own home + little inn up there one day
we try to stay in a different area + explore new towns each time. we usually like staying in an airbnb that’s a short drive away from a town with a coffee shop etc. especially if with a group. linking our airbnb’s here:
this is the house I book for my bday every year - david is the best!
this is the barn we just stayed in this trip
I shared on my IG stories that while it was beautiful, it felt a bit bare due to the lack of rugs + on windy nights it’s very creaky (and a bit spooky for me lol), there was also more ladybugs than I would like near all the windows - not sure if there’s a way to mitigate that but just wanted to share because I got so so many questions about this one
an incredible, beautifully designed cottage in old chatham - one of my faves, esp in the summer. cute area too!
now it can get very overwhelming (and unrealistic) trying to hit all the destinations you have saved in one weekend so picking your “home base” is pretty important - especially since driving far through winding dark roads at night isn’t ideal. it’s a lot easier during the day though. I say this never having driven these roads a minute of my life, but I’m simply a messenger between you guys and alex
I know upstate ny is a big generalization, and I’d prefer not to police the technicalities of borders etc. this guide is referring to the catskills & hudson valley region.
below I’ve split this guide into:
areas to stay
hotels
where to eat
where to shop
where to drink
where to acquire provisions
other activities + outdoorsy things
most of the places are my personal favorites but I’ve also added some spots I have saved + would love to visit on my next trip!
heads up before planning your trip: a lot of spots are closed monday/tuesday even wednesdays for some so check prior + plan accordingly
areas to stay:
the easiest way to think of the different areas upstate is relative to the hudson river:
on the east side you have hudson, rhinebeck, beacon, chatham, redhook etc.
on the west side you have woodstock, hunter, kingston, tannersville, saugerties etc.
you can obviously bop back and forth between the two, the river is not lava, but if you’re short on time it may result in a lot of driving and a time crunch, depending where you’re coming from. I’d build your stay around the places you most want to go to! save them to your google maps then see what areas are most populated with saves :)
if you ski/hike/prefer more of a nature centered stay: