For years, my older sisters and I looked forward to the annual autumn apple-picking trek. Spending warm days in the orchards using long picking poles to pluck only the best apples, competing to find the biggest ones, felt a bit like living in a postcard. A little later in the season, during the peak of fall foliage, that made-to-order impression grew even stronger, though our parents tended to avoid the area during that period. Too crowded, they would say.

Poughkeepsie, a classic college town on the east side of the Hudson River, is a hub of activity and a great headquarters for year-round valley vacation activities from snow sports in winter to hiking, biking, and fishing in spring and summer. Just following the winding country roads to surrounding towns makes for memorable scenic tours. My family made numerous stops here over the years for weekend getaways and when my sisters and I began visiting colleges. While the trips elicit fond memories, the downside—as you might have guessed or perhaps experienced yourself—lies in getting there.

Our chosen destinations always involved long, droning stretches on the Garden State Parkway, New York State Thruway, Interstate 84, or older state highways where the miles never passed quickly enough. Sometimes I would look up from the back seat of the car and spot Cessnas, Pipers, and Beechcraft traveling in roughly the same direction. Knowing that Poughkeepsie possessed an airport, I imagined these airplanes heading there and wondered how much sooner they might arrive.

Getting There

Fast-forward about 40 years to a trip that finally answered my question. I was flying a Cessna 172 with my instructor on my way to Hudson Valley Regional Airport (KPOU), a Class D field that pilots simply call Poughkeepsie. The time had arrived to perform the landings at a towered airport required for my private pilot certificate. Flying to Poughkeepsie from my home airport in Sussex, New Jersey (KFWN), confirmed the obvious, that even “slow” airplanes like the 172 are significantly faster than cars. The flight took less than 30 minutes, or about a third of the time required to drive.

Last summer I drove about two hours to drop off our son at a camp in Poughkeepsie. When it was time to pick him up, my wife and I flew our Commander 114B from Essex County Airport (KCDW), which is close to our home, to KPOU in 20 minutes. The flight seemed even shorter because we were able to spot our destination soon after slipping out from under the New York Class B that covers KCDW. Realistically speaking, the airplane turns a day trip into a jaunt and gives travelers more time to spend in this cool town.

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The Airport

Like many fields of a certain age, KPOU began as part of the airmail network developed during aviation’s golden age. In the run-up to World War II, it also served as a training base for the U.S. Army Air Forces and cadets at the U.S. Military Academy at West Point, just down the river.

Postwar, as passenger service blossomed, Poughkeepsie’s location roughly halfway between New York City and Albany (KALB) helped establish it as a regular stop on routes between Washington, D.C., and Canadian cities, including Montreal and Ottawa. During the 1940s and ’50s, Colonial Airlines, which flew Douglas DC-3s and DC-4s, conducted multileg flights covering territory from Ottawa to Bermuda.

From the mid-’60s through the late ’80s, commuter airline Command Airways operated a hub at KPOU with service to more than a dozen destinations from Manassas, Virginia (KHEF), to Burlington, Vermont, and including several stops in New York, ranging from John F. Kennedy International (KJFK) to Ithaca (KITH) and Binghamton (KBGM). As larger airlines began rapidly acquiring smaller carriers, they cut many destinations from their schedules. Today there are no airlines operating from Poughkeepsie, but the GA community is vibrant and welcoming.

Things to Do

The FBO, Flight Level Aviation, can help you arrange a rental car for the drive into town or beyond. On short visits we have borrowed the airport crew car to dash in for a quick meal or other errand. Taxis and rideshares are available as well. Next time I visit, I might bring my folding bike that fits neatly into the Commander’s baggage compartment. How you choose to get around will depend on how much ground you want to cover. Once in town, there is enough going on within walking distance to keep most folks busy. Poughkeepsie is also tantalizingly close to other hot spots like Kingston, New Paltz, and Rhinebeck, all within short drives.

Flying stokes my appetite, so when I arrive, I like to stop for breakfast, lunch, or coffee at one of the area’s many fun, family-run eateries such as the Poughkeepsie Grind, for breakfast and coffee, or Rossi’s, which turns out fantastic focaccia, sandwiches, and other traditional Italian fare. The range of cafes and restaurants reflects the variety you might expect in an area with so many colleges nearby. Vassar College, Marist College, and Duchess Community College are right in town, and it often helps to note where the students are eating. They will point you to the best spots.

Poughkeepsie is home to numerous art galleries, shops, and interesting boutiques. It is a good place to walk and explore neighborhoods with a range of personalities. Once again, the proliferation of schools gives the place an encouraging, youthful vibe.
When our sons were younger, this town and the surrounding area was ideal for introducing them to the notion of going to college someday, long before they grew interested in any particular school. Today our younger son has his eyes on Vassar after visiting last summer. I have noticed an uptick in his work ethic lately.

The area’s campuses are full of attractions, including galleries, tours, and sporting events. We had an architectural field day the first time we walked through the Vassar campus. It boasts a beautiful collection of Edwardian- and Victorian-style academic buildings and residence halls inside a perimeter of colonial faculty offices and homes. Then visitors come across something unexpected: Noyes Hall, a curved, stylish mid-20th century dormitory designed by Eero Saarinen. It is the kind of sight that makes you want to apply to college again.

Another must-see for those interested in history, architecture, and home decor is Locust Grove, former estate of Samuel Morse, who invented the telegraph and developed Morse Code. The 45-room home was built in 1852 on expansive grounds with views of the Hudson River. The particularly well-preserved house provides visitors with a distinct sense of well-to-do Northeast lifestyles of the 1800s. Guided tours are available.

In the interest of walking off that big meal, you can head for the Walkway Over the Hudson, one of Poughkeepsie’s truly unique attractions. The former railroad bridge stretches across the river to the town of Highland on the west bank. The span is breathtakingly high and surprisingly long—about 3 miles across and back. On previous visits, I have noticed many people if not most trekking only as far as the halfway point, which is where you get the best view. The walk is good exercise and a great experience.

While flying might make it possible to turn Poughkeepsie into an easier day trip, I would rather spend the night there and fly home the next day, or the day after. With the amazingly wide range of accommodations available, from a straightforward high-rise DoubleTree by Hilton to the Dome House Retreat in nearby New Paltz, there is something for everyone.

Editor’s Note: This story originally appeared in the MARCH 2024 issue of Plane & Pilot magazine.

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