Road Tripping: Hudson River Valley in 48 Hours

Last Updated on April 12, 2024 by Travelationship

We spent two days driving up and down the Hudson River Valley, trying to see all we could see. The valley was beautiful, with rolling hills blanketed in trees and a river carving through the whole thing. The list of possible activities, from hiking to art galleries and food choices from schnitzel to wineries, was endless. Rain trailed us on our journey for a fair amount of time, but we didn’t let it deter us. Below are some of our favorites.

Day 01 – Hudson River Valley

Strawberry Place Restaurant: Nyack, NY

It is a local institution loved by locals, travelers, and passersby. Strawberry Place is Cash Only and opens daily from 7:30 a.m. – 4 p.m. The great thing about this place is you can order anything on the menu anytime. If you want french toast at 3 p.m., done! A seat-yourself joint is pretty busy, open to close, particularly for weekend breakfast. The wait staff is more than capable; they all had a good sense of humor with a side of spunk. In addition to their standard menu, they also have a list of seasonal specials, which is how I found the delectable pumpkin pancakes with blueberries and apples.

A Visit to Saugerties Lighthouse

The lighthouse, built in 1869, is in the Esopus Estuary and is only accessible via a half-mile footpath. The tide affects the trail as it wanders through a freshwater tidal flat so the path can be submerged during high tide. There are a few boardwalks and bridges to aid your trip through the wetland sections of the park, but you should be prepared for mud. The lighthouse has gone through various stages of usefulness, but it is currently automated and operational.

Tours are available but limited to Sundays from 12 p.m. – 3 p.m. Memorial Day to Labor Day. If you have forever been on the hunt to stay in a lighthouse, this could be the place you have been dreaming of. There are two guest rooms, bed and breakfast style, available Thursday through Sunday nights year-round. As you would imagine, the reservations fill up quickly. You may need to frequent visits to their reservation page.

The lighthouse is unique as it blends function and utility nicely. It is a snazzy Italian-style brick house with a light affixed to the top. This area is a wildlife sanctuary, so please exercise diligence to pack out any trash and keep your dog on a leash. Unfortunately, it was raining while we were at the lighthouse, so the pictures came out a little unusual, but it is a spectacular place to visit.

Franklin D. Roosevelt Presidential Library and Museum

FDR piloted the U.S. ship for an unprecedented four terms through two of the country’s most challenging times. The Great Depression and World War II. He was the first president to receive a presidential library and the only one to use it in office. On his family land next to his childhood home in Hyde Park, NY, construction for his presidential library began in 1939. It ended in 1940 under the supervision of FDR, who also dabbled in architecture.

The whole complex is now run by the National Park Service, which gives guided tours of the Roosevelt Home and keeps up the grounds. If you choose to visit the presidential library, it is self-guided but does require a ticket, so either way, a stop at the park desk will be necessary. Check out our in-depth post here to learn more about the tour and library visit.

Rossi Rosticceria Deli: Poughkeepsie, NY

I was pretty excited about this place before arrival. According to Yelp, this was the best place to get a sandwich in the Hudson River Valley. It was a rainy afternoon and past lunch hour, and there was still a line, so I considered that a good sign. It is a deli in every sense of the word. You can buy ingredients or eat their precooked fare.

The choices were as endless as our line, so I had plenty of time to consider my order. I went with prosciutto and cheddar, which got me a good ribbing from the clerk, and Heather chose the roast beef. The lady at the register was beyond proficient at fielding questions, lining up deli orders, and checking you out; she also helped us into a lovely cannoli for dessert. Forget about sitting inside; you can’t do it, and the rain kept us from using the outdoor tables, so we took our food back to the hotel to eat.

Perhaps I wouldn’t have been so disappointed if I hadn’t been so excited and hungry. The prosciutto was too salty to enjoy, and Heather’s roast beef was too tough to bite into. The bright spot was the cannoli were textbook. I would give them another shot, but not their prosciutto. Find them here if you want to try them or get a cannoli.

Day 02 – The Hudson River Valley

Croton Dam

The Croton Dam fittingly rests in Croton Gorge Park and is a sight. It is a massive stone dam holding back some 19 billion gallons of water. It is so impressive it is the second-largest hewn-stone structure in the world, behind the Great Pyramid in Egypt. Building completed on this dam in 1906 took just shy of 14 years.

The other aspect of this dam that makes it so delightful to visit is its hybrid overflow system, part natural, part artificial. The water cascades down a stone staircase before funneling down a boulder-strewn spillway, creating a classic waterfall from the park below. The water stored there is part of the New York City water system.

There is only a little brown forest service sign marking “Croton Gorge Park” on the road into the dam, so keep your eyes out for it. Also, if you want a view from the top, there is an unmarked road about 200 yards up with a “Bridged Closed” sign with a few places to park. Following that road will take you to the top of the dam. One last exciting tidbit: I met two guys fishing at the base of the dam, and when I asked what they were fishing for, they said “Eels,” and they had caught several in that spot.

Kykuit, the Rockefeller Estate

Kykuit, a Dutch word for lookout, has been home to four generations of the Rockefeller family and is now a historic site of the National Trust for Historic Preservation. Situated on top of the highest point of Pocantico Hills, it overlooks Sleepy Hollow, Tarrytown, and the Hudson River; as a bonus, on a clear day, you can see the New York City skyline just 25 miles to the south.

Five different tours are available, including a couple of all-around tours and a few specialized tours; we choose the classic tour. The classic tour takes every bit of the 2 hours and 15 minutes. It states and gives you an overview of the main floor of the house, the inner garden, the west terrace, and the Coach Barn. No matter which tour you choose, they all leave via shuttle from the visitor center at Philipsburg Manor, located on Route 9 in the village of Sleepy Hollow.

The guide had a wealth of knowledge on the family, then and now, and was well versed in the property and art. Having recently visited some Newport, Rhode Island mansions, I can say that the Rockefeller Estate is a different animal, not as lavish. The Rockefellers chose to put their money into art and philanthropy. If you are a sculpture lover, you will enjoy the grounds, as they have more money invested than the house. If you want more information regarding tours and hours, check here.

Sleepy Hollow Cemetery

Heather and I grew up watching “The Legend of Sleepy Hollow” at Halloween time, and the second I found out, Sleepy Hollow was a real place, I wanted to go. What is so great about Sleepy Hollow is they embrace “The Legend of Sleepy Hollow” story and the headless horseman, examples of which can be seen throughout the town.

The cemetery is in a heavily wooded area with varying hills and has a river running through it. The original cemetery was for The Old Dutch Church of Sleepy Hollow and later expanded to the Tarrytown Cemetery. Washington Irving, the author of “The Legend of Sleepy Hollow,” requested that the cemetery’s name be changed. After his death, they granted his wish, changing it to the Sleepy Hollow Cemetery.

A bevy of notable burials included Washington Irving himself, Elizabeth Arden, and several philanthropists, including members of the Astor, Carnegie, and Rockefeller families. Several tours are available for the cemetery, all put on by the cemetery, and you can find the different listings here. The cemetery even went so far as a recreation of the bridge from the story “The Legend of Sleepy Hollow,” which was an excellent touch.

Sleepy Hollow Lighthouse (Kingsland Point Lighthouse)

The lighthouse is made of cast iron and was installed in 1883; at that time, it was a half-mile from shore. Thanks to a defunct General Motors plant constantly plowing land, the shore is within 80 feet of the lighthouse. It transitioned into automation in the mid-1950s and became obsolete in 1961 when the state added navigation lights to the Tappan Zee Bridge. To get the best view of the lighthouse or walk up to it, you must go to Kingsland Point Park in Sleepy Hollow and walk south or downriver as far as you can. There are a handful of Sundays in the summer when you can tour the lighthouse. Check this website for times and prices.

Travel Basics

RECOMMENDABLE: I can’t wait to go back! There are just that many things to see. You could easily spend a week driving up and down the river bank, having each day filled with activities and food. I would say that most popular activities involve the outdoors somehow, so keep that in mind.

See more photos on Flickr. Please look for us on Facebook, Twitter, and Instagram!