Weekend Guide to Upstate New York
Upstate New York has something fun to do during any season. Whether you want to ski, go apple picking, watch spring blossoms or splash around a lake, the region is great year-round. You can get cozy and do nothing, or you can explore the endless artisanal shops, vintage curations and amazing cuisines from expat New York City chefs. With its vast amount of wineries, adventures and activities available, you will never get tired of upstate.
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Where to stay
Playful Hunter Mountain getaway where the gorgeous common rooms and grounds are the main event.
Hudson Valley estate made for romantic escapes and rural adventures, from fishing to horseback riding.
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Gorgeous events space turned hotel, set up with standalone cabins overlooking the Hudson River.
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Day 1: Settle in and go for dinner and drinks
On a Friday night, get settled at Hutton Brickyards or Hotel Kinsley. Grab dinner at SILVIA in Woodstock, you can’t go wrong with anything on the menu.
After dinner, head to Early Terrible for drinks – it’s an eccentric bar lounge across the street with indoor trees, disco balls and art lining the walls.
Day 2: Coffee, window shopping & self care
Morning coffee and window shopping
Start your morning off with Village Coffee and Goods, a great spot with the best coffee in midtown Kingston.
Peruse some vintage goodies at Zaborski's Emporium, a four-story warehouse with found items. Take a stroll through downtown Kingston along the water, maybe grab a glass of wine at Brunette or french onion soup at Marine Harbor. Make sure to stop by Hops Petunia for the most gorgeous flowers and home decor, or head to uptown Kingston and shop – some of my personal favorite spots are Exit Nineteen, Gargoyles, Lovefield Vintage and Upstate Capital Market.
For some well-deserved relaxation, head to Birch Body Care and get a massage followed by a coffee or wine at Rough Draft Bar and Books. Birch Body Care offers services from massages to Reiki, and you will leave feeling extremely refreshed! You can also check Rough Draft’s website for upcoming events that may be happening during your stay.
Dinner and drinks
Head to Hotel Kinsley for a juicy burger and their infamous martini. Hotel Kinsley values preserving the architecture of the landmark buildings it belongs to, which gives the place a homey feel. Afterward, grab drinks at Lis Bar, where there are amazing cocktails and eastern European inspired snacks like pierogi.
Day 3: Hiking the trails
For your last day, head to Overlook Mountain in Woodstock – this hike is for moderate- to skilled-level hikers, with amazing views at the top for a reward. Looking for something easier? Try Poet's Walk in Rhinebeck.
After your hike, treat yourself in Westwind or Arrowood, where you will find amazing cideries and distilleries with fire pits, outdoor seating and overall great vibes. For your final stop, head to Ollie's for the best pizza in upstate New York.
A note from Michelle
The Ashokan Reservoir is a gorgeous walk all year round, with water views and an easy flat road.
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