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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My sisters and I still share fond recollections of meeting up with kids from other vacationing families and the resulting grade-school crushes, plucking clams and mussels from sandbars at low tide for appetizers, and listening to the local radio station, WRKO, which convinced us that FM was destined to rule over AM.

The interminable nature of the road trip was a clear downside, though, and the stay never was long enough. While giddy anticipation countered some of the boredom on the voyage from home, we could rely on the return trip for a deep letdown.

We stayed in Wellfleet, largely because that town’s quiet, rural setting was suitable for feral children. But each year the highlight was a side trip to Provincetown, which forms the hand at the tip of Cape Cod’s bending arm. It was a festive, welcoming hub in those days—the perfect escape from subdued neighboring towns. It still is, and flying in is a particular pleasure.

Plan the Flight

Starting into the flight planning from Sussex, New Jersey (KFWN) to Provincetown (KPVC) sparked nostalgia, so instead of a basic, out-and-back route, I flew an acute triangle that first took me over Buzzards Bay, Falmouth, and along the upper arm of the Cape before turning north over Chatham (KCQX) at the elbow. 

As I made my way up the forearm, I felt the anticipation return, as strong as ever, perhaps because I had not spent any time there in nearly 20 years. The excitement was at an all-time high because I was at the controls of Annie, our Commander 114B, finally living the childhood dream of flying  the length of the Cape—an endeavor that can seem to take all day in the car. At last I could look down at narrow, winding Route 6, essentially the only way in or out, and not worry about its traffic snarls.

From 3,500 feet, Wellfleet looked the same. I could see Ocean View Drive and the turnoff for the beach we frequented, where I learned to surf cast and fly aerobatic kites. Apparently the general store at the corner, where we bought patches for our inflatable rafts and eventually new rafts, is still there.

I would recommend flying “up the arm” to any pilot considering a trip to Provincetown. The flight reveals so much about this odd spit of land that seems to grow increasingly rural the farther out you go. Mile after mile of beautiful beaches unroll below until you get to the end, and suddenly there is a lot going on.

• READ MORE: Long-Distance Weather Planning For Personal Flying

Soon it was time to switch from childhood flashbacks to a sterile cockpit for the approach to Provincetown’s 3,502-foot strip. The wind favored Runway 25, which required flying north over the water to enter a right-hand pattern. A hazy sky made the ocean even less useful as a visual reference than usual. Best to stash the iPad, phone, and other loose, distracting items before beginning the descent.

With ground-hugging scrub trees on the approach end of 25 and beach on the departure end, obstacles are not much of an issue for pilots, and the runway’s generous 100-foot width makes handling gusts and crosswinds less difficult.

Airport Details

Cape Air, the island-hopping airline known for its venerable Cessna 402s, runs a brisk schedule of arrivals and departures, so the small terminal has a significant staff of TSA personnel and secure zones inside and on the ramp that GA visitors have to avoid. The $10 parking fee seemed like a nice deal compared with other Northeast resort destinations I have visited.

A pilot friend told me to bring inline skates if I ever flew to Provincetown because they are the best way to get around, and the airport is just over a mile from town. To lessen the likelihood of broken bones, I chose a Brompton folding bicycle, which another friend recommended. It was ideal on the hilly bike paths and roads that lead to Commercial Street—the teeming, scenic retail center next to the harbor.

What’s Around Town

If you enjoy walking, eating, drinking, shopping, gallery hopping and people watching, I do not think I can name a better place to visit. Long a destination for LGBTQIA+ communities, the place has a welcoming vibe that does not seem to leave anyone out. One could draw parallels with Oak Bluffs, the Martha’s Vineyard town to which African Americans and other people of color have gravitated for generations. Both places stand out as diverse, uninhibited hot spots. If you go just for the day, like I did, you might wind up feeling silly—more time is needed to fully enjoy the scene.

The Lighthouse and Other Sights

Perhaps the best reason to have a car in Provincetown, preferably with all-wheel drive, is so you can get to the Race Point Lighthouse. Race Point Road, unpaved and sandy, was too much for my folding bike, but I watched many people stop their cars and let air out of the tires in preparation for traversing the point. Race Point Beach is also a must-see. Remember, the beach is close to the departure end of 25, so you can hike there on paths around the airport. 

The tower that is visible from nearly anywhere in town is the Pilgrim Monument, completed in 1910 to commemorate the Mayflower pilgrims’ landing there in 1620. After a few weeks, they sailed on to Plymouth, now home to an airport (KPYM) that is another handy waypoint for pilots crossing Cape Cod Bay.

Cool Side Trips

Provincetown makes a nice base of operations if you want to visit Nantucket, Block Island, Martha’s Vineyard, the Hamptons, and other classic Northeast shore destinations reachable by a short flight. One problem is that you need to spend at least a week or two in any of those places to do them justice. Another potential snag is that if you start off in Provincetown, you might have a hard time finding reasons to leave.

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