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

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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. Now, I’m going to 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

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

Day 1 – Grand Central Station, Sleepy Hollow, and Tarrytown

Start your trip in New York City by fueling yourself with lunch at Vanderbilt Market food hall, right around the corner 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 heading over to nearby Tarrytown for a good night’s rest. Since Sleepy Hollow is a very tiny community with limited accommodations, it’s smarter to go to Tarrytown just five minutes away where there are way more places to stay overnight. 

Where to Stay in Tarrytown:

• 💎 Best Luxury: Westchester Marriott – A clean, upscale accommodation with shockingly reasonable nightly prices and a comprehensive on-site spa that can provide every service from hair coloring to couple’s massages. 
• 🛏️ Best Mid-Range: Courtyard by Marriott Tarrytown Westchester County – A perfectly-located hotel just two miles away from Sleepy Hollow with incredibly attentive staff and large rooms that can host up to five guests.  
• 💰 Best Budget: Hotel Nyack, a JdV by Hyatt Hotel – This bargain-priced stay located just a 15-minute drive across the Hudson River from Sleepy Hollow welcomes pets and it has a pool, gorgeous interior design, and a very convenient bar/restaurant on the premises. 

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

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.

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. 

Where to Stay in Bear Mountain State Park:

• 💎 Best Luxury: The Abbey Inn & Spa – A 4-star Peekskill hotel less than 15 minutes from Bear Mountain State Park that offers lovely touches like free bikes and rooms with river views. 
• 🛏️ Best Mid-Range: Bear Mountain Inn – A historic accommodation in the heart of the state park with charming rustic grounds and breathtaking natural surroundings.
• 💰 Best Budget: Overlook Lodge and Stone Cottages at Bear Mountain – These cute, affordable cottages have easy access to two lakes along with a restaurant and spa on-site. 

Day 3 – New Paltz and Hyde Park

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. 

Or, if you arrive during brunch hours, try out the incredible black bean burger from Lola’s Cafe (it’s by far the best veggie burger I’ve ever had). After breakfast, meander around to check out the town’s cute shops. There are so many cute, unique stores in New Paltz to discover, like Little Light of Mine Village Candle and Beans Cat Cafe.

Next, 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.

Grab lunch and a cocktail at Jar’d Wine Pub before heading 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.

Where to Stay in New Paltz and Hyde Park:

• 💎 Best Luxury: Mohonk Mountain House (New Paltz) – This swanky hotel on the banks of Lake Mohonk was founded in 1869 and feels like staying in a castle with its award-winning spa, intriguing classes available, and an on-site farm-to-table restaurant. Modern Converted Barn with Hot Tub (Hyde Park) – A one-of-a-kind pet-friendly accommodation fitting for a large group complete with great amenities like BBQ facilities and a hot tub. 
• 🛏️ Best Mid-Range:Hampton Inn by Hilton New Paltz, NY (New Paltz) – A reasonably-priced stay where guests can expect clean rooms and a very attentive staff. Inn at Bellefield Residence Inn by Marriott (Hyde Park) – Visitors love the breakfast and optimal location of this 3-star, pet-friendly stay near the Culinary Institute of America. 
• 💰 Best Budget: Americas Best Value Inn New Paltz (New Paltz) – This centrally-located stay is a dream come true for budget travelers at around $100 per night and is still walking distance into the town. Holiday Inn Express Poughkeepsie by IHG (Near Hyde Park) – A spotless hotel that offers a shockingly yummy breakfast spread and is just a little over 10 minutes from Hyde Park.  

Day 4 – The Catskill Mountains and Woodstock

Just when you thought you couldn’t head north any longer, keep going up 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. 

Continue on the scenic route toward the Catskill Mountains, the home of some of the best New York hikes.

Take a quick trek to Kaaterskill Falls, go fishing at the Ashokan Reservoir, or ski or snowboard 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 also known as the Green. On the weekends, you might be lucky enough to catch a drum circle.

For dinner, have some Mexican dishes at The Bear Cuisine. Get a few scoops at Sweet Dreams Organic Ice Cream for dessert. 

Where to Stay in Woodstock:

• 💎 Best Luxury: Woodstock Way Hotel – This high-end stay engulfed in the Catskill Mountains is the perfect combo of nature escape and pampering palace that’s even walking distance to the center of town.
• 🛏️ Best Mid-Range: Morning Glory B&B – A quaint, personality-filled accommodation that provides a delicious full breakfast each morning, a tennis court, and parking.
• 💰 Best Budget: Twin Gables of Woodstock – A surprisingly lavish boutique hotel that can lodge a family of four and has staff that makes you feel cozy as can be. 

Day 5 – Hudson, Catskill, and Albany

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).

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 drink at Chemistry Wine Bar.

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 Albany:

• 💎 Best Luxury: Morgan State House Inn – Feel like royalty in this 19th-century structure that was converted into gorgeous, well-decorated suites in the heart of the city. 
• 🛏️ Best Mid-Range: Staybridge Suites Albany Wolf Rd-Colonie Center by IHG – This accommodation makes a trip to the area effortless by offering things like a filling breakfast, an airport shuttle, and a year-round indoor pool.  
• 💰 Best Budget: Crowne Plaza Albany – The Desmond Hotel – Get both style and a good price with this stay that has spacious rooms, a fantastic location, and a welcoming hospitality team. 

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:

• 💸 Budget – SpringHill Suites by Marriott Fishkill 
• ✨ Mid-Range – The Hudson Whaler 
• 💠 Luxury – Mirbeau Inn & Spa, Rhinebeck
• 🛏️ Bed and Breakfast – Renwick Clifton House B&B 
• 👪 For Families – Elmrock Inn

Best Towns & Areas

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

• Hyde Park (Search apartments in Hyde Park)
• Hudson (Search apartments in Hudson)
• Cold Spring (Search apartments in Cold Spring)

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 stops, attractions, and hotels mentioned in this post.

Itinerary Planning Tips

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

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 waterfalls, panoramic viewpoints, some of the state’s top hiking trails, and lots of places to camp.

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

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

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 

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 

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.  

Tip #6 – Pad Your Itinerary With Local Cafes

Everyone thinks their area has the best cafes, but I really mean it! The Hudson Valley’s coffee shops are top-notch. 

To start off, don’t miss: 

• Nana’s Take Out Cafe & Sweetery (Woodstock) 
• Monkey Joe Roasting Company (Kingston) 
• The Ridge Café (New Paltz)
• Hudson Roastery (Hudson)

These cafes all make for the perfect mid-day stop to break up your itinerary. 

Tip #7 – Consider Spending an Extra Day in NYC 

With only 5 days to explore, you’ll want to spend every second soaking up the beautiful Hudson Valley region. If you can spare just one more day though, I’d suggest using it to visit Manhattan. 
NYC is only about two hours from the Hudson Valley and easy to reach on public transportation. Believe it or not, it’s very possible to get a great feel for New York City in just a day, too.

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 by far the easiest way to get around the Hudson Valley and it’s highly recommended for a short trip.

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

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.