A River Runs Through It: Weekend Train Hopping in the Hudson Valley

Many thanks to the Metro North Transit Authority, Visit Westchester NY, and Dutchess Tourism for supplying train and event tickets and for hosting me overnight on this trip. The support of businesses and organizations such as these helps me to create useful guides for readers like you. All opinions are my own.

Breakneck Ridge, Cold Spring, Garrison, Manitou. I’d glimpsed the names of these Hudson Valley towns from the window of the Metro North commuter train dozens of times before, but never did more than wonder how many miles they were to my destination in New York City. I was, I reasoned, too busy to stop at every little town along the way, regardless if it had a tranquil waterfront park or an abundance of attractive cafés and storefronts. Without noticing, I’d tumbled into the same trap that befalls many of us who live in the region: I’d treated the train as a one-and-done method for getting to the city and back again.

There isn’t much I’d like to thank the pandemic for, but it has forced me to slow down. A lot. One side benefit is that I’m getting out into, and getting to know, my local region better. I’m letting the train be my guide, taking me to cities I’ve long traveled through without a second glance—and this time I’m stopping to notice, to explore, to breathe.

Exploring Beacon

My husband and I arrived in Beacon at 10:00 a.m. on a Saturday, and struck the jackpot: the chilly weather of the past two weeks had given way to an unseasonably warm day. We had our pick of parking spots at Beacon Station. This is one of the sharp points of the double-edged sword of pandemic-depleted tourism; while devastating for local businesses, it has eased congestion in up-and-coming cities like Beacon, which throng with visitors in the warmer seasons.

We had just enough time for an amble along Long Dock Park, only a few blocks beyond the station, before boarding the Bannerman Island Tour boat. A mist enshrouded the Hudson as we motored across to Newburgh—once General George Washington’s headquarters—and idled along a handsomely renovation strip of waterfront restaurants. This isn’t a usual part of the tour, but a time-killing detour to allow the island staff to ready for visitors. I sat, listening to Lionel Richie sing over the speakers about being easy, and letting the slight breeze lift the hair off my forehead and the sun warm my bare arms.

Though most people, even those who run the boat tours, refer to the 6.5 acres of mostly barren rock as Bannerman Island, its actual name is Pollepel. In 1900, Scottish-born merchant Francis Bannerman, the world’s largest purveyor of used arms and munitions, purchased the island.

He built his storehouse—the turreted, rust-colored ruin that’s visible from the train—of Hudson River bricks, and packed it with massive stores of munitions. Nearly 125 feet up the hill from what was essentially a three-story powder keg, he built a Scottish-style castle for his family.

Even this late in the season, the manmade garden overlooking the armory was still blooming with bright pink and purple flowers that buzzed with the industry of fat, furry bumblebees and monarch butterflies. Our guide paused frequently to let the growl of a passing boat or the bleating of the train’s horn subside. A spontaneous 1920 explosion that rocked the armory, he explained, was heard for 400 miles around, and blew a 25-foot slab of building clear across the river and onto the railroad tracks, where it blocked traffic for three days. Miraculously, Bannerman’s widow and children were unharmed. In 1969, what remained of the weapons stash went up in a blazing, three-day inferno.

The tour lasted longer than expected—nearly 2.5 hours, including boat trips—and we were running late for lunch. We rushed off the docks to meet a local colleague. In the two and a half hours we were away, the streets, shops, and restaurants of the downtown had populated with people. There’s a common misconception that the upstate region grinds to a halt once the leaves drop. That may have been true a decade or two ago, but these days, if you can’t find something to do in the fall or winter, you’re probably not looking very hard.

We met at the Roundhouse, a circa-1800 brick industrial complex that was one of the city’s first factories. Following a minimalist, design-minded overhaul, it was transformed into a luxury hotel, restaurant, bar, and event space, much of it overlooking the roaring Fishkill Creek. The service was friendly, the outdoor patio humming with conversation and the splash of the waterfall just beyond its railed enclosure. We shared an oozy wheel of burrata with toast, apple slices, and blackberries as big as nickels. Over a satisfying portion of spicy lobster mac and cheese—velvety and full of flavor, if not especially spicy—I peppered my colleague with questions about the city.

After lunch, we made a quick tour of the downtown, with stops in industrial-hip Dennings Point Distillery and Glazed Over Donuts, a rustic, wood-paneled shop where you can watch through the kitchen window as bakers assemble standard cake doughnuts with customizable glaze-topping-drizzle combinations. I chose a caramel glaze, cinnamon sugar, and vanilla drizzle; my husband opts for the curious combination of lemon, graham cracker, and raspberry.

With afternoon sliding toward early evening, we scrapped our plan to try some of Beacon’s many walking and hiking trails around Madam Brett Park and Mount Beacon. Instead, we made a final stop at the Mount Gulian Historic Site. Though my colleage drove us, it’s easily accessible from the train station by bike, Uber, or Zipcar. I could see why she loves this place. Where downtown Beacon is constant movement and energy, Mount Gulian is hushed and serene, from its small Heritage Garden to the expanse of thick lawn that tumbles down to the river’s edge. The handsome wood-and-stone Dutch manor house, once used as a military headquarters during the Revolutionary War, was closed for tours, but usually hosts a variety of educational and social events, including a holiday tea.

Beyond its significance to military history, Mount Gulian boasts another important connection. James F. Brown, who was born into slavery in Maryland and escaped north via the Underground Railroad, worked here for decades as a gardener and coachman. Brown kept detailed journals of his life—some of the rare few we have that draw an authentic picture of the Black experience in early America. (He’s buried a few miles away in St. Luke’s Cemetery.)

While waiting for the train, we loitered on a small dock beside the station. Feet dangling above the water, we ate our doughnuts, licking the sticky glaze off our fingers.

Exploring Peekskill

The train chugged into motion. A few months ago, I wouldn’t have considered taking public transit. But safety protocols—and my own perspective—have evolved with our knowledge of how to travel safely and responsibly. I’ll admit that it’s a lot simpler to do when there are fewer people. The MTA estimates that train ridership is down 80 percent, meaning most times of day are low traffic and social distancing easy.

I shielded my face from the late-day sun that flashed between the trees. The extravagant colors of autumn rushed by, blending into brushstrokes of red, burgundy, gold, green, and bright yellow, an abstract painting come to life. In twenty scenic minutes, we arrived in Peekskill. A city of about 24,000, it has the gritty-artsy feeling of a town on the rise. The hilly walk from the station turned out to be a workout, albeit a rewarding one with commanding views of the river.

As Hudson River towns go, Peekskill is remarkably diverse, with significant Latinx (37 percent) and Black (19 percent) populations, and a growing number of Islamic residents. By my unofficial count, there were at least ten restaurants, coffee shops, bars, and delis, representing a wide range of global cuisines, within a five-block radius.

On South Water Street, by the river, Peekskill Brewery, decked out with small round tables under brilliant red umbrellas, was doing brisk business. Another busy spot: North and South Division streets, where the city had blocked off part of the road for outdoor dining. Looking up at the signs for Guatemalan, Mexican, Caribbean, and New American food, I wished I’d been less eager to fill up at lunch.

We detoured into Bruised Apple Books, a community landmark since 1993. The shop boasts 50,000 used, out-of-print, and rare books, plus CDs, LPs, and movies on DVD and VHS. With about 200 topic areas, it’s impossible not to find something of interest.

I lingered, as I always do in bookshops with floor-to-ceiling bookcases and floorboards that creak with years of devoted use, too long. My husband tapped my shoulder and turned the screen of his phone toward me. It was 6:00 p.m. Daylight was fading, and our train would leave in a half hour. I put down the copy of Jasper Fforde’s The Eyre Affair, its smooth cover and uncracked spine crisp in my hands, and reluctantly exited the shop.

Ignoring the blister forming under the ball of my left foot, I speed-walked back toward the station. I’d hoped to view many of the 30 public art displays, from mural to metal sculpture, located around Peekskill’s downtown. Instead, we made a hasty tour of the paintings of local artist Peter Bynum decorating an overpass, and the sculptures at Peekskill Landing Park, just in front of the train station.

With barely a minute to spare, we jogged up the steps to the platform. Sweat flecked my forehead and ringed my shoulders under my backpack straps. Across the way, the electronic board flashed a message: the train is 12 minutes late. I sighed and dropped my pack to the ground. 

Exploring Tarrytown & Nyack

During the 25-minute ride to Tarrytown, dark and fatigue set in. The hotel is about a 10-minute walk from train station, but we broke down and hailed an Uber. The doors of the DoubleTree by Hilton Hotel Tarrytown shushed open, the air-conditioning like a balm against my clammy skin. The check-in line was long, and we waited, shifting back and forth over tired feet, draining bottles of water in three gulps. Though we were given a room with two double beds instead of the requested queen, I didn’t argue. At that point, I could’ve fallen asleep on a towel in the hallway.

We ordered takeout from the hotel restaurant and headed up to the room. I’d planned to make the trip to the Sleepy Hollow Cemetery to photograph a lantern-lit night tour, but it was already after 8:00 p.m. We sat cross-legged on a bed, passing the wax-lined cardboard containers back and forth in the light of the TV, the laugh track from a rerun of The Big Bang Theory playing in the background.

Having slept a dreamless, rocklike sleep the night before, I was ready to go early in the morning. We stashed our backpacks at the hotel desk in anticipation of our first trip of the day, across the 3.6-mile expanse of the Governor Mario M. Cuomo Bridge, which connects Tarrytown to Nyack. A new pedestrian and bike path have been added along one side of the bridge, with regular Plexiglass-walled overlooks and seating areas. The pathway also features the work of a variety of local painters and sculptors, making it one of the country’s longest open-air galleries.

We used the TravelStorys app to narrate the journey. Walking close together, the volume jacked up above the ever-present noise of traffic, we listened to the histories—Native American, Dutch, and Revolutionary—of the different towns and the scenic lookouts that honor them. The Half Moon overlook, for example, pays tribute to sailors and explorers, and has a seating area shaped to mimic the prow of a ship. The Painters Point overlook, my favorite, honors the Hudson River School artists, with a bronze and wood canopy that cleverly frames Hook Mountain.

The trip took about an hour and fifteen minutes on foot. Biking shortens it to 20 minutes, but bike rental shops aren’t open before 10:00 a.m. on a Sunday, and rentals ($15 per hour or $50 per day) are in short supply as people continue to seek out novel experiences that allow for physical distancing. We exited the path on the Nyack side just as foot and bike traffic had doubled, and followed the shaded walking path into the village.

Though most shops and galleries weren’t open—either because of the time of day or pandemic restrictions on hours—we took an unhurried walk around some of the streets to admire the meticulously preserved Victorian, Greek Revival, and Federal architecture, and the cheery community garden.

We’d been on our feet for over 5 miles now, and decided to take a load off at True Food, a tiny but friendly healthy-foods café with a variety of vegetarian, vegan, and organic options. Cyclists zipped past our table—Nyack, it turns out, is one of the most bike-friendly towns in the area. I crunched into an avocado toast with microgreens and savor the easiness of the town, a quiet antidote to the commotion of the bridge.

Exploring Sleepy Hollow

For the return trip to Tarrytown, we took the mostly empty city bus—a bargain at $3—and headed a few blocks past the hotel to await the Line 13 bus into Sleepy Hollow. We’d prepared. We’d looked it up, and have $3 in cash per person at the ready. But when we stepped on, the driver informed us that a MetroCard or coins are the only accepted payment methods. Either because the bus had only a handful of riders or because we looked like people who’ve been on their feet for miles, he silently motioned us on for the 8-mile ride to the Sleepy Hollow Cemetery.

The graveyard was massive, filled with upwards of 45,000 internments, and nearly silent, despite dozens of visitors. On this 80-degree, relentlessly sunny day, we stuck mostly to the partially shaded paths, where patches of sunlight filter through the trees and dry leaves crackle underfoot. In one area, death’s-head headstones dating back to the 1700s tilted, topsy-turvy, toward one other. In another, we stared up at mausoleums larger than the average house, the final resting place of people with surnames like Rockefeller and Helmsley. We visited Andrew Carnegie’s Celtic cross–marked grave, and the modest, round-shouldered stone of Sleepy Hollow’s favorite son, Washington Irving, a skilled writer who managed to create a deeply funny and pointed story about social climbers and the spooks who love them.

We curved around the seventeenth-century Old Dutch Reformed Church, and exited through the main entrance, in search of the Headless Horseman Bridge, a crucial setting in Irving’s story. We did a double-take when we realized we’ve walked over the small concrete structure without realizing it. Twice. Since nearby Philipsburg Manor, a much-photographed 1750 English manor house, and Kykuit, the former estate of the Rockefellers, were both closed for the duration of 2020, we turned toward the downtown.

On Valley Street, in the commercial section of town, we stopped at Santorini. Old school and small, the Greek restaurant has a homey interior with chunky wood tables and chairs, tile floors, and coastal paintings on the walls. Only one other table was occupied, though a few customers filtered in to pick up orders. We took solace in the air-conditioned dining room, examining the remainder of our itinerary over stuffed grape leaves, a felafel wrap almost too large to hold, and an order of brandy-steeped saganaki that the waiter lit on fire with a flourish.   

A few blocks away, we crossed onto Main Street in Tarrytown. It’s lined with shops, restaurants, and an attractive historic Queen Anne building, composed of brick with peaked rooflines and dormers, that houses the town’s music hall. It was also lined with people, out for what would probably be the last summerlike day for six months. I peeked through doorways, but with many stores at capacity and the sun at its height in the sky, standing in line for more than a few minutes wasn’t an option. We headed back toward the train station—which is, thankfully, all downhill.

Beyond the station lies Pierson Park. Agreeable and spacious, it features a winding riverwalk, a ribbon of rocky shoreline, and a railed pier that looks out onto the Cuomo Bridge to the west and the Sleepy Hollow Lighthouse to the east.

We weren’t the only people there to enjoy the park. Families and groups of friends gathered under the pavilions or on blankets spread over the lawn. Cheerful helium balloons were tethered to the legs of picnic tables or the wrists of giggling, running children. A woman sliced a birthday cake topped with pink rosettes and dropped the squares onto plates, which another woman, so close in appearance that they must be sisters, handed around a table.   

We swerved to avoid a brindle-colored dog catching a frisbee, and padded onto the green. My husband, tired from walking since 8:00 a.m., parked himself at a picnic table in the shade of a tree, secured headphones over his ears, closed his eyes, and lay one cheek against his backpack. I left him to rest as I paced the riverwalk, snapping images of a trio of kids climbing the rocks, and a woman paddling a fire-engine-red kayak, her life vest bobbing up under her ears on the upstroke. 

Croton-on-Hudson: The Great Jack o’ Lantern Blaze

We arrived in Croton-on-Hudson for our final stop of the trip, the Great Jack o’ Lantern Blaze. I would have liked to stop at the dam and waterfall in Croton Gorge Park, but the unexpected heat of the day made walking the 3.5 miles impractical. We aimed for the village center, where Baked by Susan beckoned on South Riverside Avenue.

Bright and cheerful with a glass-walled front, the cafe is an oasis of cool and quiet. We ordered snacks and a pair of fresh-brewed iced teas, pulled up red metal chairs to a table in the corner, and plugged in our phones to charge. During our stay, only three other customers filtered in and out. It’s not a reflection on quality, but a sobering reminder of what business is like for small operators these days.   

With opening time of the Blaze at hand, we walked down the street to Van Cortlandt Manor, a seventeenth-century estate founded by an enterprising family of Dutch settlers that once owned 86,000 acres in the region. While the manor is operated as a historic house, like many museums this year, it’s closed to tours. The Great Jack o’ Lantern Blaze, which takes place on the manor’s grounds, is an exception.

Now in its fifteenth year, the 2020 Blaze was the biggest and most elaborate yet, with 7,000 pumpkins carved by a small army of artisan volunteers. Mask are required for visitors, and capacity has been reduced by two-thirds.

Before I came to the Blaze, I fully expected a rinky-dink country festival. (I say this as someone who lives in a region that hosts numerous rinky-dink fairs, and who finds them both fascinating and fun.) But right out of the gate, the Great Jack o’ Lantern Blaze surprises. I’ve seen some wild jack o’ lanterns, but not bunches of them clustered into world-famous artworks like the Mona Lisa or The Scream. Nor did I expect a rotating merry-go-round made of creepy carved horses, a spooky garden with dozens of gourd-carved eyes watching me from the trees, or a “Headless Horseman Bridge” made of dozens of jack o’ lanterns that’s far cooler than the real thing.

By the time I got to the final installation, a sprawling graveyard populated by ghoulish figures and the larger-than-life headstones—made of, you guessed it, jack o’ lanterns—of the Van Cortlandt family, I was happily speechless. 

We boarded the commuter train for our trip back to Beacon. I sank against my seat, flushed with the kind of tired that comes from new experiences and knowledge. I watched in the glow of streetlamps as my window revealed the neatly trimmed waterfront buildings of Cortlandt and Garrison and Cold Spring, towns I don’t know yet, but look forward to boarding the train for soon.

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