Last Updated on September 30, 2022 by Jim Ferri
Estimated reading time: 18 minutes
Updated for 2022 / 2023
By Jim Ferri
The Hudson River Valley is only a 45-minute drive from the busy streets of midtown New York City.
But this beautiful, peaceful and historical place couldn’t be more different than Manhattan. It’s overflowing with natural beauty, history, and culture. And it has enough farm-to-table dining options to keep any foodie busy for months. It’s also the oldest wine-producing area in the USA.
The Hudson River river is named for Henry Hudson, an Englishman sailing for the Dutch East India Company, who explored it in 1609.
More were soon to follow, including the Pilgrims, when they set sail in 1620. On that sailing, the Pilgrims were actually headed for the Hudson River Valley, not Plymouth near Cape Cod. They only turned north when they encountered low winds and shoals along the American coast.
Travelers still seek it today since it’s a perfect 2-3-day getaway from New York City.
Hudson River Valley History
In the 18th century, the river valley and its people were written about by Washington Irving, the author of Rip Van Winkle and The Legend of Sleepy Hollow. Irving is acclaimed as America’s first internationally acclaimed author.
In the 19th century, the Hudson River Valley and its river became the inspiration of the Hudson River School of landscape painting. It was not a school per se, but a group of painters influenced by romanticism and an American pastoral style.
By 1895 enough of the wealthy and hoity-toity of New York City had built homes in the Hudson River Valley that The New York Times called them “the little colony of millionaires up the river.”
How to Get to the Hudson River Valley
The best way to see the Hudson River Valley is by car since it provides you with flexibility. But if you’re not used to New York City driving, you may reconsider renting a car in NYC. After all, with the key comes the problem of navigating a way out of often-congested Manhattan.
Alternatively, you could take a short train ride to a town in the Hudson River Valley, rent a car there, and later return it before returning to NYC by train. This is quite a bit easier (and less expensive) than renting a car in Manhattan and battling its legendary traffic.
To reach the places you’ll read about here, take the Hudson Line from NYC’s Grand Central Station. The train ride to Tarrytown is less than an hour, to Poughkeepsie two hours, and to Rhinebeck about a three-hour ride total, after changing trains at Poughkeepsie.
The Hudson River Valley trip that follows is based on my drive from New York City, through the Hudson River Valley, and then returning by car to upper Manhattan. If you decide to take the train + rental-car option, you can jump in mid-trip anywhere along the way.
Driving the Hudson River Valley / Setting Out Along the River
Although you can also do this trip in reverse – starting in Sleepy Hollow – I decided to cross into New Jersey and first drive up the Hudson River’s west bank. There are a several places I wanted to see in that area.
Leave New York City via the George Washington Bridge (GWB), which connects northern Manhattan with Fort Lee, NJ. It’s actually the busiest bridge in the world, with an upper level (known locally as “the George”) and a lower level (“the Martha”). Just be sure to take the upper level and use one of the right two lanes to take exit 74, the first exit in New Jersey, for the Palisades Interstate Parkway.
It’s a scenic 42-mile ride from the GWB to New York’s Bear Mountain State Park, with about 11 miles of the parkway in New Jersey.
I decided to make a quick stop at the very first exit and drove down to the river for a nice downstream view of the river, the GWB, and the towers of Manhattan. If you stay on the parkway, about 1 mile north of Exit 1 there’s also the Rockefeller Lookout, a pull-off overlook. It’s open 24 hours a day, but there are no facilities.
At the end of the Palisades Interstate Parkway, take Exit 19 to the Perkins Memorial Drive on Bear Mountain. Follow the drive through the woods to the top of 1,284-foot Bear Mountain. During the Revolutionary War, the Americans had two forts here to block any advance up the river by the British. The views of the river from the top are still as beautiful now as they were back then.
The mountain is part of the 5,000+ acre Bear Mountain State Park, which includes hiking trails, campgrounds, etc. and the Bear Mountain Inn and restaurant. There are also Hudson River Valley cruises up the river from New York City.
Bear Mountain State Park
3006 Seven Lakes Drive
Bear Mountain, NY 10911
Tel: (845) 786-2701
On to West Point, a Famous Hudson River Valley Academy
From Bear Mountain, head north on Seven Lakes Drive toward US-202 /Route 9W. Take 9W north to West Point, about a 15-20 minute drive.
Exit at Rt 218 toward Highland Falls/West Point and follow the road, whose name changes along the way – Rt 218 / Main Street / West Point Hwy / Thayer Road. Then, on Thayer Road, turn right into the parking lot for the West Point Academy, adjacent to the West Point Museum. (You’ll know you’re at the right place by the tank on the corner at the intersection.)
All things considered, the best way to see the campus West Point and get an understanding of what you’re seeing is to take the one-hour bus tour of the grounds. Sign up for it in the Visitor’s Center to the left of the museum.
West Point Military Academy
2107 New South Post Road
West Point, NY 10996
Tel: (845) 938-0390 or (845) 938-0392
Storm King Art Center
When departing West Point, backtrack through Highland Falls the way you came in. When you reach 9W / Rt 218, turn right and continue heading north. After about 10 miles / 20 minutes, you’ll arrive at the Storm King Art Center in New Windsor, NY, an incredible 500-acre outdoor art museum, probably unlike anything you’ve ever seen.
Adjacent to Storm King Mountain, the museum presents large-scale modern and contemporary art, scattered about its 500 acres. Consequently, it’s a wonderful place to go for a relaxing walk while exploring both art and nature. It is also one of the largest collections of contemporary outdoor sculptures in the US. It’s beautiful.
Storm King Art Center
1 Museum Road
New Windsor, NY 12553
Tel: (845) 534-3115
Off to Hyde Park
After exiting Storm King, turn left and follow 9W north to US84 and the Newburgh–Beacon Bridge. Then you will have a choice.
You can continue on 9W north to the Mid-Hudson Bridge and cross the river into Poughkeepsie, a little Hudson River Valley city halfway between New York and Albany, the state’s capital.
Or you can take the Newburgh–Beacon over to the east side of the Hudson and then take US 9 north. I chose the latter since I felt it would save me some time, and I was already into the afternoon.
I took US 84 to US 9, then headed north at the town of Fishkill.
Speeding up US 9 into Hyde Park, I passed The Culinary Institute of America. It’s a place I always wanted to visit if nothing else, but to pinch a few recipes. There are four restaurants here, but you’ll need reservations.
The Culinary Institute of America
1946 Campus Drive
Hyde Park, NY 12538
Tel: (845) 452-9600
Franklin Delano Roosevelt Home
But that day, my sights were set on history, not food. I had the Franklin Delano Roosevelt Home and Presidential Library in my sights.
The Hyde Park estate was Roosevelt’s boyhood home when the Georgian colonial house was known as Springwood. Consequently, there’s plenty of Roosevelt memorabilia and the requisite Presidential Library. Nearby is the Eleanor Roosevelt National Historic Site, where the First Lady lived later in life.
Unfortunately, I had very mixed feelings about my visit. The museum, etc. was excellent, as many presidential museums/libraries tend to be. But the FDR home itself was in a state of disrepair. However, I recall seeing a sign that future repairs were slated to be undertaken.
Why was this allowed to happen? Regardless of one’s political persuasion, I don’t think any American wants to see a presidential home be left to the whims of time and weather.
Still, I much enjoyed wandering about the grounds, through the barn and fields, and seeing the grave site of Franklin and Eleanor in the garden. And I enjoyed standing on the crest of the lawn looking out across the forest to the beautiful Hudson River Valley in the distance. Make a stop here.
Franklin Delano Roosevelt Home / Library
4097 Albany Post Rd
Hyde Park, NY 12538
Tel: (845) 229-5320
The Vanderbilt Mansion
You should also stop next door at the 54-room beaux-arts Vanderbilt Mansion, another National Historic Site and remnant of the Gilded Age. It is one of several homes owned by Frederick William Vanderbilt – grandson of Commodore Cornelius Vanderbilt, the family patriarch who created the family wealth.
Surprisingly, its 200-some-odd acres are one-third of the original property. Situated on a bluff overlooking the Hudson River Valley, it has formal gardens, expansive manicured lawns, woodlands, and numerous auxiliary buildings.
The New York Times article referring to “the little colony…” described this Vanderbilt purchase as “the finest place on the Hudson between New-York and Albany.” See for yourself.
4097 Albany Post Road
Hyde Park, NY 12538
Tel: (845) 229-7770
Rhinebeck and a Special Hotel
My destination that afternoon was the Village of Rhinebeck, another 20 minutes or so north. In addition to being a pretty Hudson River Valley village, Rhinebeck also has 300 sites on the National Register of Historic Places. There are also plenty of historical mansions tucked away outside the town.
In Rhinebeck, I also wanted to see my cousins Ed and Gail, whom I hadn’t seen in a while. Thankfully at the last minute, they were able to get me a room at the famous Beekman Arms and Delamater Inn, the oldest Inn in America.
It’s a great little Hudson River Valley hotel where I was soon to join George Washington, Benedict Arnold, Alexander Hamilton, and many others who slept, ate, and drank here. The Inn’s tavern is the original traveler’s Inn, the Traphagen Tavern, built in 1704. It still has the original wide plank floor on which the founding fathers walked.
But there’s even more history at the Beekman. It was a quarrel in its tavern that precipitated the duel in which Aaron Burr killed Alexander Hamilton. Even the Continental Army gets into the picture – one of its regiments drilled on the front lawn in preparation for the American Revolution.
And though he lived just down the road, President Franklin Delano Roosevelt was also a regular guest. He concluded each of his four political campaigns for New York Governor and US President with speeches from the front porch.
Beekman Arms and Delamater Inn
6387 Mill Street
Rhinebeck, NY 12572
Tel: (845) 876-7077
Old Rhinebeck Aerodrome in the Beautiful Hudson River Valley
I was off early the next morning to another famous place in Rhinebeck, the 60+-year-old Old Rhinebeck Aerodrome. It’s America’s first flying museum of antique aircraft and replicas, with the emphasis on “flying museum.” The founder of the museum, Cole Palen, grew up in the Hudson River Valley in the 1930s firmly believing “It isn’t an airplane if it doesn’t fly.”
Today the non-profit Rhinebeck Aerodrome Museum continues to collect, restore, and exhibit more than 60 aircraft. There are also air shows and biplane rides.
Unfortunately, I got to see neither since the Aerodrome wasn’t open since I arrived mid-week. However, one of the mechanic-restorers allowed me to wander around, which in itself was quite interesting. Try to time your arrival for an airshow or a plane ride.
Rhinebeck Aerodrome Museum
9 Norton Road
Red Hook, NY 12571
Tel: (845) 752-3200
Poughkeepsie and Locust Grove Estate
When leaving Rhinebeck, drive south on Rt 9 south to Poughkeepsie, a half-hour, 18-mile drive. Settled by the Dutch in the 17th century, Poughkeepsie’s claim to fame has always been famous Vassar College, one of the top liberal arts colleges in the country. Vassar is home of the Frances Lehman Loeb Art Center, which has a good collection of ancient, medieval, Asian, European, and American art and objects.
However, today the spotlight is on the Walkway Over the Hudson, a 212-foot-high and 1¼ miles long, former railroad bridge converted into the world’s longest elevated pedestrian bridge. Linking Poughkeepsie with the town on Highland on the western bank, the bridge is now one of Poughkeepsie’s top attractions.
A 10-minute drive from the Walkway is Locust Grove Estate, the former home of Samuel Morse. It’s now a 200-acre public estate with an Italianate-style house and museum. Accordingly, given the original owner, it’s an excellent place to learn more about the invention of Morse Code, which changed communications in the world.
Locust Grove Estate
2683 South Road
Poughkeepsie, NY 12601
Tel: (845) 454-4500
A Hudson River Valley Don’t Miss: Sleepy Hollow and Tarrytown
When leaving Poughkeepsie, continue south on down US 9, NY 9A and NY 100 to Sleepy Hollow, about a 1:15 minute drive.
One of the most famous places in Sleepy Hollow is Philipsburg Manor, an 18th- century farm, milling, and trading complex that was worked by 23 slaves of African descent.
381 N Broadway
Sleepy Hollow, NY 10591
Tel: (914) 366-6900
Nearby is Kykuit, an elaborate beaux-arts house with Italianate gardens built in 1913 for John D. Rockefeller.
The Hudson River Valley country home of the Rockefellers, it’s filled with galleries of 20th-century art and beautiful furnishings.
All tours (via shuttle bus) to the house begin at the Visitors Center at Philipsburg Manor.
381 N Broadway (Visitor Center of Philipsburg Manor)
Sleepy Hollow, NY 10591
Tel: (914) 366-6900
Also nearby, a 5-minute drive from Philipsburg Manor, is the Union Church of Pocantico Hills, a small Hudson River Valley country church with steep gables. The church isn’t well-know for its architecture though, but famous for its stained-glass windows by Henri Matisse and Marc Chagall.
They were a gift to this unassuming country church from the Rockefeller family.
Here you can see Matisse’s last work, the Rose Window, and nine windows by Chagall. They’re beautiful. (tickets must be purchased online)
Union Church of Pocantico Hills
555 Bedford Road
Tarrytown, NY 10591
Tel: (914) 366-6900
More than anything else, Sleepy Hollow was made famous by Washington Irving’s “The Legend of Sleepy Hollow.”
In addition, you’ll find Irving’s grave in the famous 90-acre Sleepy Hollow Cemetery. Moreover he has some notable neighbors there, including Elizabeth Arden, Brooke Astor, Andrew Carnegie, Walter Chrysler, Samuel Gompers, and more.
You can purchase a map of the cemetery at the Philipsburg Manor museum shop across the street from the South Gate of the cemetery.
Sleepy Hollow Cemetery
540 North Broadway
Sleepy Hollow NY 10591
Tel: (914) 631-0081
On your way south to nearby Tarrytown, also visit “Sunnyside,” the picturesque, romantic home of Washington Irving on the Hudson.
Many of Irving’s characters, from the Headless Horseman to Rip Van Winkle, helped make him America’s “Founding Father of Literature.” He also penned an extensive biography of George Washington while living at Sunnyside.
Be aware that tickets for Sunnyside must be purchased online.
3 W Sunnyside Lane
Irvington, NY 10533
Tel: (914) 366-6900
Tarrytown and the Lyndhurst Mansion
In Tarrytown, you’ll discover the Lyndhurst Mansion, the southernmost of the lavish Hudson River Valley mansions. Constructed in 1838 in the Gothic Revival style, its most famous owner was Jay Gould, still remembered as one of the robber barons of America’s Gilded Age.
At Lyndhurst is a vast collection of art, antiques, and furniture, most original to Gould’s country house. It’s is surrounded by 67 landscaped acres, which include a conservatory and a rose garden. The estate also contains a turn-of-the-20th-century bowling alley and an original child’s playhouse.
It sits in a 67-acre park on the Hudson, just south of the Mario Cuomo Bridge, the southernmost of the large bridges that span the river. Incidentally, if you start your Hudson River Valley road trip in Tarrytown/Sleepy Hollow, you could cross this bridge to reach Bear Mountain (a half-hour drive) and then continue on to West Point and Storm King.
635 S Broadway
Tarrytown, NY 10591
Tel: (914) 631-4481
Driving the 38 miles to northern Manhattan via Rt 87 will take 1½ hours, depending upon traffic. Whatever you do, don’t make the trip during rush hour.
The Historic Hudson Valley is a good resource to buy tickets and stay updated regarding opening dates and times for all of the sites in Sleepy Hollow and Tarrytown listed above.
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