A Road Trip Itinerary through the Hudson Valley from Tarrytown to Albany

October is a wonderful time to take a road trip from Sleepy Hollow through the beautiful Hudson Valley to it’s northern end at Albany. Here are a few stops we recommend along the way.

Tarrytown/Sleepy Hollow

These neighboring villages, about 25 miles north of NYC, were the setting of the famous “Legend of Sleepy Hollow” (aka, the Headless Horseman) story written by Washington Irving. North Tarrytown officially adopted the name Sleepy Hollow in 1996 as a nod to its claim to fame.

While there are sites that can be visited throughout the year, the town comes alive and becomes a more exciting destination in the fall with haunted hay rides, cemetery tours, and other activities related to the legend. There is a marker where the bridge from the story used to be near a statue of the headless horseman, but there is not easy parking in the area and the road is busy.

We enjoyed seeing the Lyndhurst Mansion. There is parking on the premises and the grounds are pleasant and large, with trails for walking. The grounds are opened April through December, 9:30 to 4:30, according to the website. The gothic mansion can be toured from May to October. 

On our visit, we were disappointed to find Sunnyside Mansion, the home of Washington Irving, completely gated so there was no way we could see it, even from a distance. (We knew it would be closed but hoped to see the outside).This was in the winter, so if you’d like to see this beautiful home in person, visit during the months of May to December. The cost to tour these mansions are in the $18-$30 range.

You can also visit Irving’s grave at Sleepy Hollow Cemetery and the Old Dutch Church, a National Historic Landmark and New York’s oldest church, built in 1685.

Harriman or Bear Mountain Park

As you head north from Tarrytown, be sure to stop at one or both of these adjacent state parks. They are very large and beautiful, with a good chance of seeing a variety of wildlife at either one.

Harriman State Park offers over 200 miles of trails for hiking and biking, 31 lakes and reservoirs for swimming and boating, and facilities for camping and picnicking. It’s enormous.

When we visited, we parked at the Reeve’s Meadow Visitor’s Center and took the trail just behind it, which offered interesting rock formations, lush forest, a burbling creek, and my first ever siting of a Timber Rattlesnake, just a few feet off the trail.

In summer, you can swim or boat at Lake Tiorati and Lake Welch. In the winter, you can enjoy cross country skiing and ice skating when conditions allow.

Bear Mountain State Park has many attractions to interest family members of any age. There is a small zoo, a playground, and even an antique but functional Merry-go-Round (check to see if it’s open before you visit if this is on your list of things to do.) All of this can be reached easily from the main entrance and parking lot at the lodge.

You can also hike or drive to the mountain top at Perkin’s Peek. We drove there in April and found it snowing with a wicked wind. It was invigorating for us to run to the viewing tower and the views at the top were, of course, worth the climb.

State parks in New York typically cost $5 or $10 for a daily vehicle pass.

Hyde Park

Hyde Park is a town along the Hudson in Dutchess County, NY known for the following attractions:

Springwood and the Museum and Library of FDR – the grounds, mansion, library and museum are all worth visiting, and you can easily spend half a day here, depending on the attention spans of your youngest family members. The resting place of the Roosevelts sits beneath a simple white headstone in the middle of a large flower garden behind the library. The stables with the names of his horses can also be visited – you’ll see the stable formerly belonging to “New Deal.”

The Vanderbilt Estate – again, the grounds are just as impressive as the mansion, with space and views that make it worth a visit, even if the mansion is closed. Tours of the mansion are $15 per adult (children and free), and the grounds are free. There is an Italian Garden complete with fountains and benches to sit and take in the Hudson in from the mansion’s back yard. The estate is just across the street from Springwood in Hyde Park, so both visits can be done easily in a day.

Albany

From Hyde Park to Albany is over an hour, but there are lovely villages where you can stop along the way, such as Kingston or Catskill if you want to break up the drive.

Albany is, of course, the capital of New York, and the New York State Museum is also here. Park near the Empire State Plaza to visit both buildings. The museum is free, and the capitol can be toured for free at 10, 12 or 2 on week days – you can just walk into the lobby. Even if you are not there at that time, the building is open from 7 to 7, Monday to Friday.

The plaza is a pleasant place to walk, with fountains and surrounded by interesting architecture, such as the Egg – something of an oddity that houses theaters. We found easy street parking and little crowds on a weeknight in summer, and enjoyed walking the plaza and seeing these attractions.