Hudson Valley Travel–What To Know Before You Plan Your Trip

If you want to visit New York but need help determining what part of the state, consider spending some time in the Hudson Valley. Located two hours north of the Big Apple, the Hudson Valley has historical attractions, wineries, and amazing outdoor adventures. Before you plan that itinerary, having a short geography lesson on the Hudson Valley is essential – it's bigger than you think. 

Hudson Valley Travel-Everything You Need To Know

The Hudson Valley area extends 150 miles from Manhattan to New York's capital, Albany. It's divided into three sections: upper, middle, and lower. Depending on how long you have to visit, you can hit some highlights in each section or concentrate on one and see as much as possible. 

Remember, however, that planning a visit to “Upstate New York” will differ depending on who you ask. For most people who live here, upstate New York is any Hudson Valley area beyond Westchester County, while others debate that upstate is way up north, past Albany. It’s easier to plan your trip by focusing on the three areas of the Hudson Valley instead of what’s considered upstate. 

I've lived in both the lower and middle parts of the Hudson Valley my entire life and visited the upper many times, so here are my must-see recommendations, but it wasn't easy to choose.

Lower Hudson Valley

The lower Hudson Valley includes Westchester and Rockland counties, and its history surrounds the wealthy Van Cortlandts, Philips, and the Rockefellers, who owned much of the land. Take tours of their breathtaking estates, starting with the Kykuit, a Rockefeller estate in Sleepy Hollow. Four generations of the Rockefellers lived in this Colonial-style mansion built in 1913. Depending on the tour, you can visit both floors and the art galleries, Inner Garden, golf room, and Coach Barn.

Another sight to behold is the Lyndhurst Mansion, located in Tarrytown – a short drive from Sleepy Hollow – and sits right on the Hudson River. This gothic-style home sits on 67 acres, was designed in 1838, and became the seasonal home of Wall Street tycoon Jay Gould. The tours can include up to five floors, more than 25 rooms, a parlor, a grand art gallery with an impressive collection of European paintings, and more.

Less than 15 minutes away is Washington Irving’s Sunnyside, which is less opulent but as important to our history of literature. Washington Irving created legendary characters like the Headless Horseman and Rip Van Winkle, and you can see where he wrote The Legend of Sleepy Hollow. 

Ride The Trails

There's more to do in Westchester and Rockland counties than touring historical sites, but it's a great place to start. If you can hitch your bike on a road trip here, there is an amazing 750-mile Empire State Trail where bicyclists and hikers can explore New York State on repurposed historic railroad beds. It starts in New York City and reaches the Adirondacks, but you can ride some of it in the Hudson Valley. For an extra sightseeing bonus, plan your trip in the fall when the leaves change colors. It's a sight to behold. 

Finally, if your vacation must include an amusement park, Playland in Rye, New York, is where you must be. It's almost a century old, and some rides are still from the original 1928 opening (my favorite is The Whip) and can still be ridden. 

Middle Hudson Valley 

This region encompasses the counties of Putnam, Orange, Dutchess, and Ulster. Starting in Dutchess County, check out the ruins of the beautiful Bannerman Castle located in Beacon on Pompeii Island. Named after its builder Frank Bannerman, a fire partially destroyed the castle, which was once considered haunted. A 2-½ hour tour, accessible by boat, brings you to the castle, where they also hold special events such as movie nights and themed Titanic dinners. 

There’s more history to see here, too, including tours of the Vanderbilt Mansion and the home of Franklin D. Roosevelt, both national sites in Hyde Park. After touring them, enjoy a meal down the street at the Culinary Institute of America, where some of today’s famed chefs, such as Cat Cora, Amanda Freitag, and Anne Burrell, have studied. My favorite CIA restaurant is Ristorante Caterina de' Medici (Italian cuisine), but there are other options. 

If you want to walk around and explore a specific town, I suggest either Beacon or Rhinebeck (about a half hour apart from each other). Both offer a variety of mom-and-pop shops, art galleries, and great restaurants. Rhinebeck is also home to The Beekman Arms and Delamater Inn, which has been open since before the Revolutionary War. In Orange County, you can feel like a kid again and bring the kids to the Legoland theme park in Goshen. The rides are fun – don't miss Lego Ninjago The Ride! – and stay at the themed hotel so you will feel like you’re in a Lego building. They also have a water park so you can cool off. 

Upper Hudson Valley

Greene, Columbia, Albany, and Rensselaer counties are rounding out the upper Hudson Valley. Here, the Catskill Mountains and the area's outdoor beauty take precedence. Hop on board The Catskill Mountain Railroad (CMRR), a heritage railroad based in Kingston, New York, that began operations in 1982. This ride brings you up close and personal through some of the oldest farmlands in the United States across Esopus Creek and then up Hurley Mountain (and, again, those leaves in fall!).  

If skiing is your thing, a trip to Hunter Mountain Resort is excellent for novice or accomplished skiers and snow tubers. Finally, sit back, relax, and enjoy a drink while you enjoy the scenery in the Hudson Valley, known for its wide selection of craft breweries and wineries in each county.  

Extra Tips You Need to Know 

• Many historical homes are closed year-round, and guided tours are only available some weekdays, so check schedules beforehand. 
• For most, photography is only allowed on the grounds, not inside homes.
• Ticket prices vary depending on the level you purchase. A longer, higher level will allow you to see more of the home and other floors. 
• Many do not allow children under five on the tours.

Of course, no matter where you visit, your journey to the Hudson Valley will only be completed with a close-up tour of our Hudson River. Hudson River Cruises offers views of the Rondout and Esopus Meadows lighthouses, waterfront mansions like Lyndhurst and The Vanderbilt Mansion, and much more.