A bridge over the Hudson River during autumn season

5 Day Hudson Valley Itinerary for 2022 (The Perfect Planner)

If you’re looking for an epic Hudson Valley itinerary for your upcoming New York trip, then you’ve come to the right place. New York’s Hudson Valley region along the Hudson River is a hot spot for prime restaurants, art, and expansive natural beauty, but the sheer number of things to see and do can make planning a trip difficult.

Luckily, this former Hudson Valley-ian took all the work out of it and planned the ultimate 5-day itinerary in the Hudson Valley for you. I’ll spill the best outdoor locations, contemporary art exhibits, and the best places to stay in the Hudson Valley. All you need is five days to explore some of the best things to do in the Hudson Valley

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5 Day Hudson Valley Itinerary

Day 1 – Grand Central Station and Sleepy Hollow

View of people inside the Grand Central Station in New York
(photo: Mariusz Lopusiewicz / Shutterstock)

Starting your trip in New York City, begin by fueling yourself with lunch at Urbanspace food hall, two blocks from Grand Central Station. With your hunger quelled, walk to the train station and make sure to soak in its prominent pop culture past. It’s probably been featured in at least two of your favorite movies or TV shows. 

Next, take the 45-minute (ish) train to Tarrytown and then grab a taxi to the charming village of Sleepy Hollow. Alternatively, you could rent a car in Tarrytown (search Discover Cars for the best prices) and drive straight to Sleepy Hollow in Westchester County. This is still considered the Lower Hudson Valley because it’s right on the Hudson River.

Once you’re in Sleepy Hollow, head to the impressive Rockefeller Estate that once housed the legendary Rockefeller Family. Discover its formal gardens and art in one of the finest collections ever owned. Then, dip into more local history at the Philipsburg Manor and the Old Dutch Church. 

Grab dinner at Bridge View Tavern before closing out the first day of your trip. 

Day 2 – Bear Mountain State Park and Storm King Art Center

A red sculpture under the clear blue sky in Storm King Art Center
(photo: Matthew Poveromo / Shutterstock)

Day two of your Hudson Valley itinerary is all about nature and the arts; two things the area is known for. When you wake up, grab breakfast and drive 30 minutes along the Hudson River to Bear Mountain State Park. Spend the afternoon on the hiking trails and enjoying the lake activities. If you want to extend the day, stay a night at the Bear Mountain Inn

From here, keep driving north, stopping at West Point or Cold Spring. In Cold Spring, you can visit the lovely gardens of the Boscobel House. Keep heading north until you reach the Storm King Art Center in New Windsor. After wandering the outdoor sculpture park, have lunch at Mi Sazón Boricua. 

Stop at Storm King Mountain 10 minutes away to relax and take in the views, and then drive over to Ziatun in Beacon for dinner. To cap off the day, grab some drinks and play retro games at Happy Valley Arcade Bar. 

👉 Pro Tip: Another great place to stop in this area is DIA Beacon. It’s a very interesting modern art museum. Or, for more history, make a detour to the George Washington Washington Headquarters State Historic Site in Newburgh. 

Day 3 – New Paltz and Hyde Park

The clear blue sky over the Mohonk Preserve Testimonial Gateway
(photo: Brian Logan Photography / Shutterstock)

On the morning of day three, continue heading north to New Paltz on the west side of the river. It’s a little over 30 minutes away. When you arrive, try the eggs benedict from Main Street Bistro in the heart of town. 

After breakfast, take advantage of New Paltz’s rich array of outdoor activities. Try rock climbing or hiking at Minnewaska. Go apple picking at Twin Star Orchards and check out their cidery, Brooklyn Cider House. Have lunch and a cocktail at Huckleberry before going to Hyde Park in Dutchess County over on the east side of the river. 

In Hyde Park, get ready for an extra helping of history. Start with a visit to the Franklin D. Roosevelt Presidential Library and Museum. Then, go to the Home of Franklin D. Roosevelt, a National Historic Site, followed by Vanderbilt Mansion. Order a pizza pie from Ronzoni for dinner.

Day 4 – The Catskill Mountains and Woodstock

A colorful staircase going to the entrance of a boutique store in Woodstock
(photo: James Kirkikis / Shutterstock)

Just when you thought you couldn’t head north any longer, keep going north along the Hudson River towards Woodstock. On the way, stop in Kingston for food and drinks. Get coffee from Monkey Joe Roasting Company and a breakfast burrito from Sissy’s Cafe. 

Then, continue on the scenic route toward the Catskill Mountains, the home of some incredible New York hikes. Take a quick trek to Kaaterskill Falls or go fishing at the Ashokan Reservoir. Or, go skiing or snowboarding at Hunter or Windham Mountain in the winter. Now that you’ve really gotten in touch with the Hudson Valley’s nature, venture over to Woodstock. 

Woodstock, the original Hippie town, is home to some of the best things to do in the Hudson Valley. See what’s going on at the Bearsville Theater or The Colony. Make sure you walk to the core of Woodstock, the Town Center, also known as the Green. On the weekends, you might be lucky enough to catch a drum circle.

For dinner, have some Mexican cuisine at The Bear Cuisine. Get a few scoops at Nancy’s of Woodstock Artisinal Creamery for dessert. 

Day 5 – Hudson, Catskill, and Albany

Cars parked along the side of Warren Street in Downtown Hudson
(photo: quiggyt4 / Shutterstock)

On the last day of your itinerary, you’ll hit three different Hudson Valley cities so you’ll need a big breakfast. Munch down on a dish from Oriole 9 (everything on the menu is delicious). Then, make your way to the town of Hudson and go through the quaint vintage shops. Afterward, go to Warren Street for lunch. My top choice is always Swoon Kitchenbar or Nolita’s Cafe.

Next, travel to the town of Catskill. Do a quick, easy-going nature walk at RamsHorn-Livingston Audubon Sanctuary. Soak in the surrounding landscape. Then, have a delicious beer at Crossroads Brewing Company.

Finish the itinerary in the state capital of Albany. Hop aboard a Hudson River sightseeing cruise to get a new perspective on the area. Visit the New York State Capitol site and Washington Park. Have global cuisine with top-notch wine at Yono’s for your final meal.

Where to Stay in the Hudson Valley

Best Hotels 

There are all different types of hotels to stay at in the Hudson Valley and they come at varying price points. Here are some of the best options for all budgets:

Best Towns & Areas

Aerial view of the Mohonk Mountain House in New Paltz
(photo: Photo Spirit / Shutterstock)

The Hudson Valley is made up of many great New York towns and counties. Some of my top recommendations for places to stay are: 

Check out the full-length guide on where to stay in the Hudson Valley

Itinerary Planning Tips

Tip #1 – Appreciate the Hudson Valley’s Abundant Nature 

Overlooking view of a waterfall in Hudson Valley

One of my favorite things about the Hudson Valley is that there’s truly endless nature to explore throughout the area. There are many beautiful New York waterfalls, panoramic viewpoints, and some of New York’s top hiking trails. Make sure you plan to add at least an afternoon of discovering the area’s nature into your itinerary. 

Tip #2 – Book Accommodations Ahead of Time

The Beekman Arms Inn from the outside and its sign
(photo: James Kirkikis / Shutterstock)

New York state as a whole is very expensive. It’s not just New York City. Unless you have a large budget, a spontaneous trip to the Hudson Valley isn’t recommended. So, before you start exploring everything New York state has to offer, pre-book your accommodations in advance. 

Tip #3 – The Best Way to Get Around is Renting a Car

Scenic view while driving under the clear blue sky in Hudson Valley

There are several modes of transportation that can get you around the Hudson Valley. You can grab the Metro North train or the bus. However, the best way to get around the Hudson Valley efficiently on a five-day trip is by renting a car. Before you commit to a car rental, don’t forget to check out Discover Cars to compare local rates.  

Tip #4 – Check Out the Weather and Decide the Best Time to Visit 

Tourists enjoying their day in Hudson Valley

The best time to visit NY for your five-day trip depends on what you want to do. People who want to go skiing and sip hot cocoa should come from mid-December to March. Travelers who relish warm weather activities should arrive from May to September. Take stock of the activities on your itinerary and choose the ideal season for them. 

Tip #5 – Check Out Some of the Hudson Valley’s Museums and Historical Sites 

The Franklin D. Roosevelt Presidential Library and Museum from the outside
(photo: Michael Gordon / Shutterstock)

New York museums and historical sites are among the best in the entire world. When you’re visiting the New York area, it’s practically a necessity to see some of them. 

My top recommendations are: 

  • West Point Museum 
  • Hudson Valley MOCA
  • DIA Art Foundation
  • Staatsburgh State Historic Site
  • Home of FDR National Historic Site
  • Senate House State Historic Site

Even if you can only squeeze one or two into your itinerary, it’ll give you some valuable insight into New York history.  

***

You’re fully equipped to take on five days in the Hudson Valley. Planning on finishing off your trip in New York City? Make sure you read our 21 NYC travel tips before you take on the city that never sleeps.

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