Historic Homes, Bike Trails, and Family Fun: Things To Do In the Hudson Valley

Catskill Mountains Hudson Valley

If you want to visit New York but need help determining where, 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 for you to enjoy. If you're looking for fun things to do in the Hudson Valley, keep reading for ideas. 

But before you plan that itinerary, having a short geography lesson on the Hudson Valley is essential – it's bigger than you think. 

Hudson Valley 101

The Hudson Valley NY area extends 150 miles from right above 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 a few highlights in each area or concentrate on one area and see as much as possible. 

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. I have to admit, it wasn't easy to choose, so I recommend visiting the Hudson Valley Tourism website for even more ideas. 

Lower Hudson Valley

The lower Hudson Valley includes Westchester and Rockland counties, and its history surrounds the wealthy Van Cortlandts, Philipses, and the Rockefellers, who owned much of the land. Here you can take tours of their breathtaking estates, such as the Kykuit, a Rockefeller estate in Sleepy Hollow. Four generations of the Rockefellers lived in this Colonial-style mansion built in 1913. Depending on your chosen tour, you can visit one or both floors and the art galleries, inner garden, golf room, and coach barn.

Another estate to behold is the Lyndhurst Mansion, located in Tarrytown – a short drive from Sleepy Hollow that sits right on the Hudson River, an extra added perk. This gothic-style home sits on 67 acres, was designed in 1838, and became the seasonal home of Wall Street tycoon Jay Gould. Tour options include up to five floors, more than 25 rooms, a parlor, a grand art gallery with an impressive collection of European paintings, and more. There's lots of stair climbing!

Less than 15 minutes away in Irvington is Washington Irving's Sunnyside, which is less opulent but is important to our history of literature. Washington Irving created legendary characters like the Headless Horseman and Rip Van Winkle, and here 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. 

The Rail Trail starts in New York City and reaches the Adirondacks, but you can ride some of it in each section of the Hudson Valley. For an extra sightseeing bonus, plan your trip in the fall when the leaves change colors. It's a memorable sight. 

And, finally, if your vacation must include an amusement park, Playland in Rye, New York, is where you need to be. It's almost a century old, and some rides, still there from the original 1928 opening (my favorite is The Whip), 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 two-and-a-half 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 in Hyde Park, both National Historic Sites. 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 graduated. My favorite restaurant is Ristorante Caterina de' Medici (Italian cuisine), but other options exist. 

From Small Towns to LEGOLAND – There's More!

If you want to walk around and explore a small town, I suggest either Beacon or Rhinebeck, which are about half hour apart from each other. Both offer a variety of mom-and-pop shops, art galleries, and fabulous 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 (although I went with my adult daughter and there was still plenty for us to do.) 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 round out the upper Hudson Valley. Here, the beautiful Catskill Mountains 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 to some of the oldest farmlands in the United States across Esopus Creek and then up Hurley Mountain, offering you another chance to peep at those leaves in the fall.   

If skiing is your thing, book a winter trip here to Hunter Mountain Resort which is excellent for both novice and accomplished skiers and snow tubers. 

Other Things To Know About Visiting Historic Homes

Make sure to check schedules for tours of historical homes in advance. Many have limited hours of operation. 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 historic homes do not allow children under five on the tours. 

Best Time to Visit

The best time to book your trip to the Hudson Valley depends on who you ask, but typically most tourists visit in the spring and summer. My favorite time here is in the fall when it's a little cooler, the leaves are beautiful (end of September to the beginning of October.) The historical attractions are still open and it's nice enough for long hikes. 

Some historic sites host limited winter hours but they decorate the estates for the holidays. Of course, it gets very cold here in the winter (until March) and the chance for snow is high. In addition to Hunter Mountain, you can ski and snow tube at Fahnestock Winter Park in Carmel and Mount Peter in Warwick. 

Getting to the Hudson Valley

From Manhattan to the Catskills is roughly 220 miles by car on the highway. If you live or are visiting New York City, and want to take a side trek to visit the Hudson Valley, there are trains from both Grand Central Station and Penn Station that take you here.

You should know that once you get here you'll need a car to get around depending on where you go. Westchester is a bit-more public transportation friendly, but the more north you go, things are more spread out, so while Uber is available, your costs will definitely increase. 

Plan Your Own Adventure and Visit the Hudson Valley

Don't forget to sit back, relax, and enjoy a drink while you enjoy the Hudson Valley scenery in one of the many craft breweries and wineries you can find in each county. 

Of course, no matter where you visit, your journey to the Hudson Valley will only be complete 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.