How To Spend An Amazing Three Days In Upstate New York

Chances are a whirlwind week of exploring New York City is on your bucket list.

And we get it! Those flashing lights, the energy of the city, and the endless locations to snap photos are hard to beat.

While we love the energy that New York City brings, it can get overwhelming after a while. No wonder New Yorkers love to get away for the weekend and drive upstate!

Coming from the Pacific Northwest, Berty and I yearned to see trees and forests once again after a fast-paced time in NYC. We decided to book a cozy Airbnb and spend three days in Upstate New York, getting our fix of nature and mountains once again.

If you’re looking for that perfect balance of city living and forest escapes, we’ve created the perfect Upstate NY itinerary for you.

Read on to discover how you can easily plan three days in Upstate New York for the ultimate city getaway!

Rustic Black Cabin in Upstate New York
Shot with Canon EOS R – 24mm 1/6400s f/4 ISO1000

How To Spend An Amazing Three Days In Upstate New York

This post was made possible by the amazing team at B&H Photo! We appreciate their support of creatives and their pursuit of community.

Starting your trip to New York City? Read This:

Where is Upstate New York?

When our three-day itinerary in Upstate New York was confirmed, we quickly started telling people “we’re going Upstate!”. The nearly predictable next question from New Yorkers was “That’s great! Where to?”

After a lot of curious questioning, Berty and I realized that the term “Upstate New York” can really refer to nearly everywhere else in the state BUT New York City. 

Now, if you’re unfamiliar with New York, it’s actually a HUGE state! This total area of New York covers almost 55,000 square miles. Outside of NYC, most of the state has rivers, mountains, forest, lakes, and farmland.

Being from the PNW, Berty and I loved the idea of exploring this nature-filled part of the state. We also need to return and drive around Vermont, New Hampshire, and Maine. New England road trips in the fall sound like an absolute dream!

Now that you know you have tons of options for your three days in Upstate New York, here are some suggested places and areas to visit:

  • Hudson Valley (cute, small towns, historic charm)
  • Catskill Mountains (outdoor adventures and hiking opportunities)
  • Ithaca, New York (Finger Lakes Region, boating, kayaking, etc)
  • Buffalo, NY (Niagara Falls, Sports, good for families)
  • Adirondack Mountains (hiking and backpacking)
  • Syracuse, NY (Finger Lakes, lots of boating opportunities)

(We’ll be talking about the Catskill Mountains region in this post, so if that piques your interest, read on!)

Beautiful farmland and fall colors in Upstate New York
Canon EOS R 24mm 1/1600s f/4 – ISO 1000

Three Day Itinerary in Upstate New York

This post is sponsored by B&H Photo

Below, you’ll find an example three-day Upstate New York itinerary from our latest trip to the Catskill Mountains.

This weekend was full of scenic drives, hikes, waterfalls, and lots of New York adventures. We’ll be sharing places to stay in Upstate New York, things to do, and restaurant recommendations.

Where exactly are the Catskill Mountains Located?

The Catskill Mountains are located via a three-hour drive north of the city. This is one of the more popular places to take a weekend getaway in Upstate New York because of its close proximity to New York City.

On your drive, you’ll be surprised how quickly the scenery becomes rural, compared to the dense skyscrapers of NYC. Just a half-hour outside of the city, you’re likely to see farming fields, barns, and beautiful forest-lined roads.

Some of the most popular places to stay in the Catskill Mountains are in Woodstock, Phoenicia, Shandaken, and Hunter. Each of these small towns has its own unique feel and vibe to them!

Also, click here to get $40 off your first Airbnb booking to stay in that dream cabin or farmhouse Upstate!

Map of The Catskill Mountain Area of Upstate New York

Day 1:

Drive To The Catskill Mountains Via Small Highways For Your Three Days In Upstate New York

One of the great things about a weekend in Upstate New York is the endless backroad options, perfect for scenic drives. We found ourselves frequently pulling over to take pictures along the roads (just make sure to watch for cars around the corners!).

There are countless options to veer off course and get yourself lost – in a fun way, of course!

Driving the small highways are great options any time of year, but the roads are especially beautiful in the autumn season. You’ll frequently come across colorful side roads and gorgeous tree-lined bends in the highway.

Some scenic Upstate New York highways to consider for those leisurely drives:

  • New York State Route 28 for Catskills fall foliage (From Kingston to Pine Hill)
  • New York State Route 55 for waterfalls, swimming holes, and reservoirs (From Modena To Liberty)
  • Highway 214 for small towns, cute cabins, and one-off forest roads (From Phoenecia to Tannersville)
  • Highway 23A for epic waterfalls, hikes, and camping (Through the Kaaterskill Wild Forest)

Read More: 30 Essentials You Need To Be Packing For A Road Trip

Scenic Drives - Three Days In The Catskill Mountains

Day 2:

Explore Kaaterskill Falls And Other Nearby Upstate New York Hikes

One of the highlights of the mountains in Upstate New York is the Kaaterskill Falls hike. This amazing New York waterfall has two tiers reaching 260 feet total.

This means it’s one of the highest waterfalls in the state of New York and one of the highest in the eastern United States!

There are two trailheads that reach the three-tiered falls (respectively called “upper” and “lower” trailhead). There are viewing platforms from above the falls and below. Each of these areas hold their own unique and beautiful perspectives of Kaaterskill Falls.

Pro Tip: We suggest starting on the Upper Trailhead of Kaaterskill Falls. This trail will bring you to a stunning viewing platform of the falls, and a short and sweet trail to reach the base if you wish to go further.

Read More: The Complete Guide To Hiking Kaaterskill Falls Trail In Upstate New York

Kaaterskill Falls - Upstate New York Weekend Itinerary

Other Amazing Hikes In Upstate New York To Consider

Kaaterskill Falls is only one of the several awesome trails to take during your three days in Upstate New York. There are countless trails that will have you returning to this area again and again.

If you live in the city, here are several hikes in New York State to take to get outside in nature. You’ll be glad you did!

Day 3:

Stop In Upstate New York Small Towns For Shopping and Restaurants

Our three days in Upstate New York really left us with our imaginations running wild! This area of the Catskill Mountains was chock-full of historic houses, rustic cabins, and adorable small towns.

Here are some of our favorite small towns in Upstate New York, and what you can expect when visiting.

Phoenicia, New York

This darling town in the middle of the Catskill Mountain area is the perfect pit stop for meals or grabbing groceries. This is also a great town to try glamping in New York because you can sleep in a treehouse, geodesic dome, or even a canvas tent, and still be close to modern conveniences and amenities!

You can also find some really cute curated stores for some local shopping. Here are some of our favorites:

Phoenicia, New York - Three Days In Upstate New York Itinerary

Woodstock, New York

Contrary to popular belief, Woodstock, NY is actually NOT the place where the historic music festival was held. While the historic festival was actually held on a rural site in Bethel, New York. However, Woodstock still pays tribute to the hippie, counter-culture of its time.

Here, you’ll find eclectic gift shops, darling cafes, and several farms that bring the small-town feel to life. During our three days in Upstate New York, we stayed at an Airbnb just outside of the main town of Woodstock, in a beautiful cabin in the woods!

Our Favorite Stops In Woodstock:

  • Bread Alone Bakery. Excellent place for on-the-go freshly-baked pastries and bread, with quality coffee. It also has an eat-in side of the cafe for a slower breakfast.
  • Yum Yum Noodle Bar. Wide selection of Asian cuisine. We can vouch for their pho and sake. It was so good!
Woodstock - Three Days In Upstate New York - Itinerary


A weekend in Upstate New York is the perfect amount of time to get away from the hustle and bustle of the city. This area of the state of New York has so much to offer, especially in the rest and relaxation area.

Berty and I strongly believe in a balanced life, and that means knowing when to take a break and get away for a few days! We hope this example of a three day Upstate New York itinerary will inspire you to take your own relaxing trip soon!

How would you spend three days in Upstate New York? What are some other ideas for amazing weekend getaways from New York City? We’d love to hear your thoughts in the comments below!


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  1. whoah this blog is excellent i love studying your posts. Keep up the good paintings! You know, a lot of people are searching round for this info, you can help them greatly.

  2. A perfect 3 day trip, coming from a local! Kaaterskill Falls is one of our favorite local spots to head to in the summer/fall. Next time you’re in this area though, be sure to spend some time on the Shawangunk Ridge, on the Mohonk and Minnewaska properties. So many incredible little zones, and an amazing little town of New Paltz is right there for dinner and drinks afterward!

    1. Thank you, Jason, for your sweet comment! Thank you for the additional suggestions as well, I know we missed so many things during our short trip Upstate! We will definitely try to hit up the places you suggested on a return trip. 🙂