3 Amazing Winter Trips to Upstate New York from New York City
Upstate New York is one of the best winter escapes if you’re looking to go on a scenic road trip. With its snowy landscapes, charming little towns, and cozy places to stay, it’s the perfect destination for a winter getaway. In this blog post, I’m sharing three of my favorite winter escapes in Upstate NY—from beautiful Sullivan County, to the scenic Catskills and serene Finger Lakes areas.
“For those who prefer to take the back roads home”
Upstate NY Winter TRIP #1: Sullivan County (Eldred, Narrowsburg, Callicoon, Bethel)
Sullivan County along the Delaware River, is home to some of the most charming small towns. They are all within a two-hour drive of Manhattan, so its very accessible for a short getaway or even a day trip to Upstate NY.
Where to stay in Sullivan County?
Cedar Brook House in Eldred, NY
Sullivan County has countless accommodations, but I loved Cedar Brook House in Eldred! It’s a peaceful retreat surrounded by a private pond and a small brook. We found it easy to unwind here, whether we were relaxing indoors by the fireplace or exploring the beautiful grounds. If you're looking for a quiet getaway, I highly recommend it.
What to do in Sullivan County?
TAKE A DAY TRIP TO DOWNTOWN NARROWSBURG, NY
In winter, Narrowsburg radiates charm. I love just taking a stroll through the town’s vibrant Main Street, where there are several locally-owned boutiques, art galleries, and antique stores. If you're feeling adventurous, the nearby trails offer winter hiking.
Where to eat in Sullivan County?
THE TASTING ROOM AT Seminary Hill Orchard & Cidery in callicoon, NY
43 Wagner Ln.
Callicoon, NY 12723
For a delicious farm-to-table meal with panoramic views of orchards and rolling hills, The Tasting Room at Seminary Hill is a must-visit. The menu adapts to the seasons, featuring ingredients sourced from local farms.
TO KNOW: Seminary Hill also has a hotel, The Boarding House. Although I haven’t had the chance to stay here yet, it seems like a wonderful option for anyone planning to visit the Sullivan County area.
THE LOCAL TABLE AND TAP ALONG KAUNEONGA LAKE IN BETHEL, NY
3 Horseshoe Lake Rd.
Kauneonga Lake, NY 12749
The Local Table and Tap in Bethel, NY, is a lakeside restaurant with all the laid-back Catskills vibes. We stumbled upon this gem one time while near Woodstock, NY, and have been going back every chance we’re in the area. The staff is friendly, the atmosphere is homey, and so far I’ve enjoyed everything on their menu. My favorites so far are the bulgogi beef lettuce wraps, tuna poke bowl, and sticky chicken lo mein noodle bowl - to name a few :)
For more on Sullivan County, check out their travel guide here.
Upstate NY Winter TRIP #2: tannersville and hunter
Just a 2.5-hour drive from Manhattan, Hunter and Tannersville—less than 10 minutes apart—offer a picturesque, storybook setting in Upstate NY, perfect for a winter escape and filling your lungs with refreshing mountain air.
a winter wonderland DRIVE TO tannersville and HUNTER
As you approach Tannersville and Hunter, I recommend stopping at Notch Lake (along NY-214 by Elka Park) for some of the most epic winter drive views you can imagine.
Arriving in Hunter, NY
Where to stay in Hunter/Tannersville, NY?
Contemporary Cabin in the Catskill Mountains in round top, ny
Tucked away in the Catskill Mountains, this contemporary cabin on Airbnb I stayed in perfectly blends modern and rustic with cozy comfort. The floor-to-ceiling windows soak in the sunlight during the day, while the fireplace keeps you warm and toasty at night. If you’re looking for an entire place to rent that’s near both Hunter and Tannersville, this Airbnb is a nice option.
What to do in Hunter/Tannersville, NY?
My ideal day in Hunter starts with a morning stop at Fellow Mountain Cafe for a coffee and a cinnamon roll, though their full menu offers plenty of delicious options to choose from.
Fellow Mountain Cafe
7883 Main St.
Hunter, NY 12442
Then, I recommend going to Downtown Tannersville, where you can check out unique shops. My two favorites are Sundry, a boutique with spectacular home goods and apothecary items, and Camp Catskill for all wonderful things outdoors.
Where to eat in Hunter/Tannersville, NY
Deer mountain inn in tannersville, ny
790 Co Rd 25
Tannersville, NY 12485
Up in the hills of Tannersville, the restaurant at Deer Mountain Inn is elegant and cozy. We enjoyed dinner here with friends and it was the perfect setting for good conversation while enjoying good food. The space is full of rustic charm with a fireplace, wooden interiors, and mountain views. The seasonal menu focuses on locally sourced ingredients, creating dishes that bring to life the Catskills.
TO KNOW: Deer Mountain Inn isn’t just a restaurant — it’s a boutique hotel. If you can, consider booking your stay—it’s conveniently located and I think would be a memorable retreat.
Tabla in tannersville, ny
6033 Main St.
Tannersville, NY 12485
Tabla is a Mediterranean and Italian-inspired restaurant in the heart of Tannersville. I loved the small plates and creative cocktails. The ambiance is especially charming in the evening, so I highly recommend booking a dinner reservation.
Upstate NY Winter TRIP #3: FINGER LAKES (ITHACA)
If you’re willing to venture a couple more hours outside of New York City, within a four-hour drive you’ll arrive in Ithaca in the Finger Lakes region. Years ago, I visited Cornell University but never had the chance to explore Ithaca itself. Ithaca turned out to be a stunning extended weekend escape, and getting to see waterfalls and natural gorges in the winter added an element of awe we were after. Not to mention the artsy vibe of a lakefront town. Ithaca has it all and I can’t wait to see other parts of the Finger Lakes region.
Where to stay in Ithaca, NY?
Ithaca Marriott Downtown on the Commons
120 South Aurora Street
Ithaca, NY, 14850
As a Marriott Bonvoy member, I tend to book a Marriott property when they offer a solid option—especially for city-center stays. The Ithaca Marriott Downtown on the Commons checked all the boxes for location and comfort, plus it came with a great view of downtown Ithaca.
What to do in Ithaca, NY?
Taughannock Falls State Park
Ithaca is home to 150 waterfalls, but Taughannock Falls State Park is the ultimate must-see, in my opinion. At 215 feet, it’s the “tallest free-falling waterfall east of the Mississippi—even higher than Niagara Falls.” It truly is breathtaking to approach Taughannock Falls and feel the power of the water plunging below.
ithaca falls on fall creek
Ithaca Falls on Fall Creek is a peaceful hidden gem just a few minutes from downtown. Unlike some of the more remote waterfalls in the Finger Lakes, this one is incredibly easy to access—just a short walk from the small parking lot or nearby streets.
For more on Ithaca check out Visit Ithaca.
Upstate New York in the winter is pure magic. Whether you’re exploring the quiet beauty of Sullivan County, the rugged winter scenery of the Catskills, or the peaceful natural wonders of the Finger Lakes, each destination offers its unique charm. A scenic road trip through these regions is the perfect way to embrace the season, slow down, and experience the quieter side of New York. So bundle up, hit the road, and discover just how special winter in Upstate NY can be!
For more on New York, check out my other blog posts:
Top 5 Best Day Trips to Upstate New York from New York City
Escape to Upstate New York: Memorable Day and Weekend Getaways
One Perfect Day in Hudson: A Dog-Friendly Haven in Upstate New York
Day Trip to Montauk, New York, Off-Season
Greenport, NY Getaway: How to Enjoy a Day on Long Island’s North Fork
Explore NYC in 3 Days: The Perfect Itinerary for Photography Enthusiasts
5 Ways to Experience a Lesser-known New York City That Will Amaze You
City of Dreams: Your Guide to the Best of New York City
SoHo Morning Magic: A Local's Guide to the Perfect Start
10 Hidden Gems and Activities in and Around Williamsburg, Brooklyn
A Perfect Day in Dumbo, Brooklyn: 12-Hour Guide
The 10 Best Things to Do in Williamsburg, Brooklyn, from a Local