My Ultimate Guide to Upstate New York
Upstate New York has become a true home away from home for my family. I didn’t grow up here, but I chose it. Max and I started coming upstate in our early 20s when we were just dating, and over the years, it’s become our sanctuary. It’s where we escape city chaos, celebrate birthdays and baby moons, host friends, take slow walks, and make fast memories. Now that we’re raising our kids here, the connection feels even deeper. There’s just something about the pace, the people, and the mix of nature and creativity that makes this part of New York so magical.
Whether you’re coming for a weekend getaway, a cozy cabin stay, or to experience the rich culture that thrives in small towns and rolling mountains, this guide has you covered. These are my personal must-dos, plus a full breakdown by area for planning the perfect upstate escape.
Upstate: My Absolute Musts
These are the places I always recommend when friends ask for a “what should we do upstate?” list, some are iconic, some are hidden gems, and all of them hold memories for me.
Art Omi
A dreamy outdoor sculpture park in Ghent, ideal for a slow afternoon walk with a coffee in hand and kids or dogs running free. It's whimsical, inspiring, and just the right amount of weird in the best way.
Fortunes Ice Cream
Seasonal, small-batch ice cream made with local dairy and inventive flavors. It’s a must-stop if you're anywhere near Tivoli.
Troutbeck
My go-to for a romantic weekend (especially in the fall or winter). It’s luxurious in a way that feels completely unpretentious, fireside cocktails, dreamy rooms, and incredible food in a historic estate.
Stissing House
A beautifully restored 18th-century inn that’s perfect for a cozy dinner by the fire. The food is seasonal and soulful. Ideal for winter nights when you want to feel transported.
Chleo
Farm-to-table dining in Kingston done exceptionally well. The flavors are so intentional, and the space feels stylish and relaxed. A go-to date night pick.
West Kill Mountain Hike
A tougher hike, but the Catskill views at the top are so worth it. Pair it with a visit to West Kill Brewing afterwards and it’s the perfect day.
Overlook Mountain
A more accessible hike with a cool payoff: sweeping views and a hotel ruin at the summit.
Woodstock Infusions
Hot yoga, cold brew, and a little stream out back, this place always re-centers me. I try to pop in for a class and coffee every time I’m in Woodstock.
Rough Draft Bar & Books
A perfect rainy day stop: indie books, great coffee, and even better wine. Grab a pastry and post up for an hour, or three.
Apres l’amour
This boutique is a mix of sustainable fashion, local artistry, and cool girl energy. It also hosts events and creative community gatherings I love.
Upstate Down
A dream space of curated real estate, design objects, and that signature upstate aesthetic. Even if you’re not house hunting, it’s fun to browse.
Poet’s Walk
An easy, family-friendly stroll with wide open views of the Hudson River. Bring a picnic blanket and stay a while.
Rose Hill Farm
Pick-your-own apples, peaches, and berries, plus cider tasting and flower fields that are straight out of a dream.
Ollie’s Pizza
Located in High Falls, and worth the drive for the best pizza. The onion pie is elite.
Cassis
A stylish little tasting room that feels more like Napa than the Hudson Valley. Wine, small bites, and gorgeous interiors.
Field + Supply
A curated makers market hosted at theHutton Brickyards. I plan weekends around it, it’s that good. From handmade goods to vintage finds and local eats, it’s worth the trip every time.
Other personal favorites worth a shoutout:
Fantze Bagels: chewy, fluffy perfection.
Proprietors: vintage fashion finds with serious style.
Gracie’s Diner: don’t sleep on the breakfast sandwich or the mountain views.
Cafe Mutton: get anything on the menu, trust me.
Montgomery Place Orchards: the sweetest little farm stand.
Good Night: Asian fusion in the coziest, buzziest space.
Westwind Orchard: live music, cider, apple picking, wood-fired pizza, family heaven.
The five areas, and which one you actually want
Upstate is not a destination, it is about six of them, and people routinely book a place two hours from the thing they came for. This is the part worth getting right before you look at a single hotel.
Kingston is the practical base and the one I would put a first-time visitor in. It has the most restaurants per square foot, the Rondout waterfront, and it sits where the Catskills and the Hudson Valley meet, which means almost everything else on this list is inside an hour. It is also the least precious of the towns, in a good way.
Woodstock and the eastern Catskills is where you go for the mountains and the mythology. Overlook Mountain starts here, the town is small and walkable and busy on weekends, and the drive in is the point. Stay here if you want to hike in the morning without getting in a car first.
Hudson and Columbia County, on the east side of the river, is the design and antiques end. Warren Street is the most concentrated good shopping anywhere upstate and the restaurants are the most ambitious. It feels more like a small city than a mountain town, and it is a solid ninety minutes from Woodstock, which surprises people.
Rhinebeck and Red Hook is the gentlest version of upstate and the easiest with small children. Flat, pretty, walkable villages, Poet’s Walk and the river estates nearby, and Amtrak stops at Rhinecliff, so it is the one area you can reach without a car.
The western Catskills, out toward Phoenicia, Livingston Manor and the Beaverkill, is the quiet one. Fewer restaurants, more river, better fly fishing, and the closest thing to real remoteness within three hours of the city. Go here when the point is to not see anyone.
I would pick one of these and stay put. Two bases in a long weekend is how you end up spending the weekend driving.
Which side of the river, and why it matters
There are only a handful of bridges, and crossing one costs you twenty minutes to half an hour every time. Sort out on day one whether your weekend is a west side weekend, which is Kingston, Woodstock, Saugerties and the mountains, or an east side weekend, which is Hudson, Rhinebeck, Tivoli and the farms. Then mostly stay there. The crossing is beautiful and you do not want to do it four times.
When to come, and what people get wrong about fall
Fall is the reason most people come, and the timing is more specific than the internet suggests. In the higher Catskills, peak color usually lands in the first half of October. Along the river and further south it runs a week or two later, often into the third week. If you book the last weekend of October hoping for peak, you are frequently looking at bare branches up high and a lot of brown.
The thing nobody tells you is that the weekend either side of peak is better than peak itself, because the color is genuinely good and the roads and the orchards are not at a standstill. Columbus Day weekend is the single busiest weekend of the year up here, and it is worth avoiding unless the crowd is part of what you want.
Late spring, from mid May into June, is the underrated season. Everything is green, the waterfalls are full, and you can get a table anywhere. March and early April are mud season and I would not send anyone then.
Summer is swimming holes, farm stands and long evenings, and it is lovely, though August can be humid. Winter is quiet and cheap and genuinely beautiful after snow, with the caveat that a lot of the smaller places close mid week.
Getting here, and how much you need a car
Amtrak runs up the east bank of the Hudson with stops at Poughkeepsie, Rhinecliff and Hudson, and the ride itself is one of the better train journeys in the country. If you are staying in Rhinebeck or Hudson you can genuinely do a weekend without driving.
Everywhere else, you need a car. Kingston has no passenger rail, the buses are infrequent, and cell service in the mountains is unreliable enough that you should download your maps before you leave. Nothing about upstate works on ride shares once you are out of the towns.
What I would skip
Trying to do the Catskills and Hudson in the same weekend. Peak foliage weekend without a dinner reservation booked well ahead, because the good restaurants fill weeks out in October. And I would skip the impulse to fill the days. The reason this place works is the pace, and a weekend with two plans in it is better than one with six.
How we book Upstate
This is home, so the upstate bookings we do tend to be about matching the area to the group, getting into the handful of places worth the trip on the weekend you actually want, and knowing which properties are lovely in September and grim in March. If you would rather hand the whole thing over, get in touch.
Explore By Area: Tune in on Substack
Looking for an easier more fluid way to plan you upstate trip? It’s taken me years (5+ to be exact) to accumulate my break out by region (think Kingston versus New Paltz versus Hudson and about 7 more towns that are close but not that close that you could do it all in a day. Head over to my substack, subscribe, and then continue planning your upstate weekends for years to come! The guide is updated quarterly since we constantly see new openings and closings across the region. And if the city or the beach is part of the same summer, my NYC guide and my Hamptons guide are the other two I keep updated.
Upstate NY: My Home Away From City Life
Upstate has become such a special part of my story, seasonal beauty, slower moments, and spaces that inspire. Whether you’re visiting for the first time or rediscovering it with new eyes, there’s always more to explore.
Ready to plan your Upstate escape?
Let me help you design a getaway that’s curated, cozy, and full of local charm.
Reach out to start planning
With love, Michelle
