5 Day Hudson Valley Itinerary (A Perfect Planner + Map) (2024)

👉 Jump to: Day 1 | Day 2 | Day 3 | Day 4 | Day 5 | Where to Stay | Map | Tips | FAQs

🖨️ Get a free, printable version of my Hudson Valley road trip itinerary here!

Looking for an epic Hudson Valley itinerary for your upcoming New York trip? 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.

I’m a former Hudson Valley-ian and I’ve planned the ultimate 5-day itinerary for you. I’ll share the best outdoor locations, contemporary art exhibits, and even the best places to stay in the Hudson Valley.

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5 Day Hudson Valley Itinerary

Day 1 – Grand Central Station and Sleepy Hollow

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Start your trip in New York City 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

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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

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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 co*cktail 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

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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 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

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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

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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.

Hudson Valley Itinerary Map

Here is a Google Map with all the stop, attractions, and hotels mentioned in this post.

Itinerary Planning Tips

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

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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

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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

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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

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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

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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.

FAQs About Hudson Valley Itinerary

Is the Hudson Valley worth visiting?

The Hudson Valley is definitely worth visiting. It’s home to charming and unique towns, a rich arts scene, beautiful nature attractions, and so much more.

Do you need a car to get around the Hudson Valley?

You don’t technically need a car to get around the Hudson Valley, as you can utilize the Metro North train or the bus. However, having a car is the easiest way to get around the Hudson Valley.


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 NYC travel tips before you take on the city that never sleeps.

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5 Day Hudson Valley Itinerary (A Perfect Planner + Map) (2024)


Which side of the Hudson River is more scenic? ›

The Hudson River's west side is a scenic drive for art lovers. Follow Route 9W as it hugs the Hudson River's western banks for a ride to artsy outposts and historic towns.

Where to stop in Hudson Valley? ›

  • Home of Franklin D. Roosevelt National Historic Site. 1,264. ...
  • Kykuit, The Rockefeller Estate. 790. Gardens. ...
  • Olana State Historic Site. 835. Architectural Buildings. ...
  • New York State Capitol. 869. ...
  • Vanderbilt Mansion National Historic Site. 1,152. ...
  • Pride of the Hudson. 867. ...
  • The Culinary Institute of America. 827. ...
  • Lyndhurst. 586.

What highway follows the Hudson River? ›

Route description. The New York segment of US 9 can be divided into the section south of Albany, which parallels the Hudson River closely, and the portion north of Albany, which takes in a long section of the eastern Adirondacks.

How do you spend a day in the Hudson Valley? ›

New York on a Budget: Free and Low Cost Things to Do in Hudson...
  1. Trek across the Walkway over the Hudson. ...
  2. Hike the Appalachian Trail. ...
  3. Experience the best of Beacon. ...
  4. Visit a brewery, cidery, winery, or distillery. ...
  5. Make new friends at the farm or zoo. ...
  6. Travel the Wallkill Valley Rail Trail. ...
  7. View art under the open sky.
Mar 21, 2023

What is the prettiest town in the Hudson Valley? ›

World Atlas names 5 Hudson Valley towns the most picturesque in New York. See the list
  • Sleepy Hollow, NY. Sleepy Hollow, a village located within the town of Mount Pleasant in Westchester, is home to all of the above. ...
  • New Paltz, NY. ...
  • Kingston, NY. ...
  • Saugerties, NY.
Apr 4, 2024

How long is the Scenic Hudson RiverWalk? ›

The parks is a segment of the county's planned 51-mile RiverWalk and adjacent to Tarrytown's Pierson Park.

What is the safest city in the Hudson Valley NY? ›

The Town of Bedford is No. 1 for safety in a report published by Safewise. Six other areas in the Hudson Valley also made the top 10. They include East Fishkill, Hyde Park, Carmel, Yorktown, Orangetown and New Rochelle.

What is special in Hudson Valley? ›

The Hudson Valley is a National Heritage Area that has inspired painters, poets, essayists, and novelists for centuries. It is home to the Forever Wild Catskill Park and the oldest continuous settlement in the nation.

Do you need a car in the Hudson Valley? ›

The Hudson Valley is a sprawling region carved by waterways, bursting with mountains and dotted with dozens of towns. If you're looking to veer off the well-trod path, driving is the easiest way to do it, but you don't need four wheels to see the top sites.

What major city is connected to the Hudson River? ›

It originates in the Adirondack Mountains of upstate New York at Henderson Lake in the town of Newcomb, and flows southward through the Hudson Valley to the New York Harbor between New York City and Jersey City, eventually draining into the Atlantic Ocean at Upper New York Bay.

What is the name of the tunnel under the Hudson River? ›

The first Hudson River vehicular crossing, the Holland Tunnel connects Canal Street in Manhattan with 12th and 14th streets in Jersey City, NJ, and is considered an outstanding engineering achievement.

Is the Taconic Parkway scenic? ›

It has been praised for the beauty of not only the surrounding landscape and views it offers, but the way the road itself integrates with and presents them.

Is Beacon worth visiting? ›

Beacon is a great day trip, but if you're willing to shell out a little cash and stay overnight, it is well worth your while. Enter, The Roundhouse, a beautiful cluster of restored industrial buildings looming over Fishkill Creek, at the foot of Beacon Falls, and the east end of Main Street.

What is the average income in the Hudson Valley? ›

What are the median and average incomes in Hudson Valley?
Y-o-Y Change
Average Household Income$139,1087.5%
Median Household Income$106,3753.1%
People below Poverty Level201,0103.7%
People above Poverty Level1,845,0003.0%

Where is the cleanest part of the Hudson River? ›

The Poughkeepsie Drinking Water Intake area, Stony Point Mid-channel and Croton Point Beach all had the lowest failures at 3%.

What is on either side of the Hudson River? ›

Middle Hudson Valley

With its rolling hills and magnificent estates as well as the Shawangunk and Catskill Moutains ranges, this region is known for its scenic and historic treasures. As the river narrows, the banks on either side of the Hudson are dominated by the majestic Hudson Highlands.

Is the Hudson Line scenic? ›

The Hudson Line is one of 3 different lines operated under the Metro North Railroad. It is classified as the green line. This is the most scenic train ride you can take to see most of the Hudson River Valley.

Can you swim in any part of the Hudson River? ›

The short answer is “Yes!” The long answer is that it depends on when and where. Issues like sewage outflow and algal blooms keep many areas along the Hudson from being swimmable, particularly after rainfall.

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