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 the Hutton 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.
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.
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
