Best Towns to Visit in the Hudson Valley

Who wants to get out of the big city to go to another big city? Come and spend some time in our fun, unique, and quirky neighboring towns with our guide to the best towns to visit in the Hudson Valley. Need some help planning an itinerary? Call us! We love to share our favorite places, and we want your getaway to be relaxing and fun! It’s hard to believe that all of these places are just an hour away from New York City!


Cornwall is a short 10 minutes drive to the east of Caldwell House right on the Hudson River.  It is a small town of about 3,000 inhabitants recently brought into prominence by being selected by HGTV’s Home Town Kickstart program

Out of thousands of applicants, Cornwall was chosen to be featured as one of six small towns to receive a facelift. Three areas of town were updated: a public space, a business, and a “local hero.”  In Cornwall, a pedestrian bridge, a local photography/children’s shop, and a firefighter were updated. So for fun, go visit the boutique (246 Main St), walk across the pedestrian bridge (on Bridge St), and check out the local sculpture.

If you are looking for more sculptures, Cornwall is the place to find them. The Storm King Art Center is also located in Cornwall. The Storm King is a 500-acre outdoor museum with large-scale sculptures and site-specific installations living under the open sky. Permanent exhibits as well as changing artworks may be viewed by reserving a timed-entry ticket.


Newburgh is a 20-minute drive north of Caldwell House and is also located on the Hudson River. Follow the cobblestone streets up from Mount St. Mary’s College and down Liberty to get a feel for the history; peek up some of the streets for a view of the large mansions that overlook the Hudson.

Visit the first publicly owned historic site, George Washington’s Headquarters. The home that he stayed in is called the Hasbrouck House, and it is his longest residence at any headquarters during the Revolutionary War. Furnished to reflect the time period, it is open for tours. Before you leave, don’t miss the magnificent views of the Hudson River.

The waterfront in Newburgh is home to many great restaurants. Some of our favorites include Blu Pointe, Il Cena’colo, Liberty St Bistro, and Iron Chef.


Across the river from Newburgh, is Beacon. Beacon is known for a number of historical locations and for being a mecca for modern art. First, let’s start with the history. The Madam Brett Homestead was built in the early 1700s and was inhabited by the same family for 7 generations, until the 1950s. The house and grounds are now maintained by the DAR and can be toured. If you love historic homes, you can also visit the exterior of the Bogardus-DeWindt House.

Another fun activity is to hike to Dennings Point in the Hudson Highlands State Park and see the ruins of an old Brick Works. If you prefer staying close to the water, visit Long Dock Park. Take a kayak tour, go fishing, or simply sit and enjoy the water.

For a cultural adventure, you must visit Dia Beacon! This museum of contemporary art is one of 11 locations that house the Dia Art’s collection from the 1960s to the present. The museum is a renovated Nabisco printing plant situated on 31 acres next to the river. Since Dia opened in 2003, the number of galleries in Beacon has blossomed. Beacon celebrates art gallery walks on the second Saturday of the month, but it is fun to stroll the galleries at any time.

Fort Montgomery

Fort Montgomery is a 15-minute drive southeast of Caldwell House. One of the primary sites to see is the namesake Fort Montgomery. The Fort covers 14 acres and was the location of a particularly brutal battle for control of the Hudson River. More than half the Patriots were killed or wounded.

On a cheerier note, Fort Montgomery is also the location of the Orange County Arboretum. The Arboretum has 35 acres of various themed gardens and woodlands. It is a beautiful place to wander, relax and enjoy the plantings. It is located in Thomas Bull Memorial Park, which is another great spot for picnicking or fishing.

New Windsor

New Windsor is a 10-minute drive north of Caldwell House. It has about 3,000 residents with a number of parks and a great military museum. The National Purple Heart Hall of Honor was established to collect, preserve, and share the stories of all recipients of the purple heart.  There are over 1.8 million recipients of the purple heart since it was established in 1782. George Washington helped design the original purple heart, and designated that it should be awarded to soldiers who displayed “not only instances of unusual gallantry in battle, but also extraordinary fidelity and essential service in any way.” 

Shunnemunk State Park is partially located in New Windsor; it has wonderful hiking trails with amazing views of the Hudson. Also located in this town is Kowawese Unique Area at Plum Point. Kowawese is the native American word for place of small pines. The term “unique” was coined to describe the beauty of the area’s vistas and habitats.

These best small towns in the Hudson Valley offer so many fun activities; from art and sculpture museums to hiking trails and historical sites to amazing dining. Who needs the big city? Start planning your getaway to the Hudson Valley and its most romantic getaway at the Caldwell House!

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