The Food-Obsessed Traveler’s Guide to Road Tripping Through the Hudson Valley

New York State offers many verdant vacation destinations, most notably the Catskills, the Finger Lakes, and the Adirondacks. The Hudson Valley, which stretches from Westchester to Albany along both banks of the river, has never quite come into its own among them, being more a place for driving through rather than for lingering.

Yet apart from the wide, lazy river itself, and cliffs that tower on either side, the region has charms all its own, from numerous farm stands, to historical monuments predating the American Revolution, to a diversifying catalog of restaurants. I recently spent a week motoring through the Hudson Valley. Below, follow along through my travels, and perhaps take it along on your own road trip through the area, including a little detour to Massachusetts.

Poughkeepsie

After a recent piece extolling the Oaxacan food of New York City and New Brunswick, tipsters contacted me asking why I hadn’t included Poughkeepsie. This river town is home to effete Vassar College, but also has a thriving immigrant food scene, including more than a dozen Mexican restaurants. The phenomenon is not limited to Poughkeepsie: Cantinas of a modest sort have popped up on both sides of the river, so that you’re never far from a plate of enchiladas or a well-stuffed quesadilla in the Hudson Valley.

My traveling companion and I pulled up for lunch at Cocina Oaxaquena, a two-year-old Mexican café on a stretch of Poughkeepsie’s Main Street. The lime green interior had been freshly painted and is now decorated with hand-painted mural of Mexican pyramids. The menu featured commonplace dishes from several regions of the country, plus the usual burritos and nachos, though a sizable portion was devoted to Oaxacan and Pueblan cuisines.

Slathered with refried black beans, the tlayudas (crunchy round Oaxacan flatbreads) were magnificent in size and lushness of toppings, while the memelas had been freshly hand-patted. A place of this modest sort isn’t going to spend days making ancient moles, but there was a delightful version of chicken enmoladas — freeform enchiladas smothered in a Oaxacan black mole that was darker, sweeter, and toastier than mole poblano.

Across the river and into Newburgh

It’s a bit hard to get back in the car and see straight after eating such a gigantic meal. As we drove up the river on the eastern bank, we stayed on Rt. 9, which initially cleaves to the waterfront, but eventually veers off. It’s much slower than taking the Taconic or the New York Thruway, but well worth the extra time. Almost immediately we spotted the former railroad bridge now known as the Walkway Over the Hudson, which allows hikers and bicyclists to cross the river between Poughkeepsie and Highland, New York.

We drove northward through Hyde Park, home of FDR and the CIA (Culinary Institute of America), with its sprawling campus and public cafes and restaurants we chose not to stop at. Then past the Vanderbilt mansion, and though the towns of Rhinebeck and Red Hook. All along the way, we noticed barbecues, sometimes located in rambling wood frame houses with front lawns and outdoor seating. We’d eaten previously at Revenge BBQ (Irvington), uphill from the Hudson with views of the river, and found it excellent.

Hudson Valley’s list of barbecues restaurants is astounding. On my current list of places to check out: Round Up Texas BBQ (Cold Spring), Northern Smoke (Carmel), Barnstormer Barbeque (Ft. Montgomery), Pig Pit (Cohoes), Holy Smoke (Mahopac), Hickory BBQ Smokehouse (Kingston), Smoky Rock (Rhinebeck), American Glory (Hudson), Billy Bob’s BBQ (Poughkeepsie), Pik Nik BBQ (Tarrytown), Capital Q Smokehouse (Albany), Southbound BBQ (Chestnut Ridge), and at least 10 more. I’d recently been to Billy Joe’s Ribworks in Newburgh, and found the ribs and chicken, at least, to be tasty. These places tend to be open longer hours in the summer, when vacationers migrate upstate.

Claverack

After over a half day of driving, we reached our base camp in Claverack, just east of the railroad town of Hudson — which overlooks the river but doesn’t make much of its waterfront. Searching around in the vicinity for local specialties, we stumbled on the hot pepperoni hero. This Italian-American sandwich is made by slicing up a pepperoni, flooding it with marinara, and then stewing it in the tomato sauce until the normally hard sausage turns into delicious mush.

We found a great version at Keeler’s Eskimo Bar in Claverack. A soft hero loaf had been slit in the center, and the bright red pepperoni stew sluiced in. After trying to eat the thing like a regular Italian hero, we discovered that you are much better off using a knife and fork. The pepperoni tasted like a different meat product than when it appears on a pizza, with the black pepper standing out and orange paprika oil that seeped from the sausage fortifying the sauce.

The ice cream stand’s menu was littered with culinary oddities. Another is the Michigan dog, which turned out to be a regular hot dog in a bun smothered in red ground-meat sauce. This sauce didn’t taste like chili, but was sweet, flavored with bell pepper and onions like a sloppy joe. It tasted a lot like the loose meat sauce served on a bun and called Spanish hamburger in Milwaukee.

Indeed, the Hudson Valley and adjacent regions are crazy for hot dogs. While tube steaks have suffered discredit in New York City, and our consumption has doubtlessly decreased over the last half-century, along the river they are considered a regular meal, bought from trucks and quaint freestanding stores that have playful identities. In Troy, New York, just north of Albany, Famous Lunch (which originated in 1932) serves tiny hot dogs in tiny buns, topped with a ground-meat mélange called “zippy sauce.”

North Adams in Massachusetts

One day we darted across the nearby Massachusetts border to North Adams to tour the labyrinthine MASS MoCA (Massachusetts Museum of Contemporary Art), which occupies a former textile mill in the middle of town, now filled with massive art installations in a dozen high-ceilinged galleries. Naturally, we couldn’t resist stopping at Jack’s Hot Dog Stand, founded in 1917.

The hot dogs there are smallish, too, with a catalog of possible toppings that included chili, sauerkraut, mustard, mayo, bacon, and cheese, the latter not liquid but wrapped around the frank in slices. But when we saw the fresh looking patties of raw beef sail through the kitchen, we got a hamburger simply topped with mayo and bacon, and it was one of the best burgers we’d tried all year. We ate a second lunch at Korean Garden, where a drab cinderblock structure hides some very good and inexpensive Korean food.

Stephentown and Philmont

On the way back from North Adams to Claverack, we stopped at Gardner’s Ice Cream in Stephentown, one of the many soft-serve joints that still blanket Columbia County and come alive in the summers. The chocolate dipped cone tasted as great as the ones we remembered from childhood, and the nut-covered hot fudge sundae was great, too.

Just northeast of Claverack lies the hilly town of Philmont, which once boasted 17 textile mills. Now, it’s famous for its spectacular 150-foot waterfall, which can be enjoyed in an hour-long hike. Ensconced in an old filling station is Local 111, a hickster restaurant. It does a great job of using locally sourced meat and produce via chef and owner Josephine Proul. We loved the smoked lamb meatballs, but what really knocked us out was a twist on avocado toast that featured a slice of zucchini bread topped with sheep’s milk cheese, fresh peas, microgreens, pickled rhubarb, and crushed pistachios. Somehow, it worked.

Hudson

Next up is Hudson, the only Amtrak station before the state capital of Albany and frequently a disembarkation point for summer visitors and residents alike. Fancy restaurants line picturesque Warren Street, some of them quite good, others totally mediocre. There are probably 15 places where you can blow $75 dollars apiece on dinner, making it seem like Fort Greene in Brooklyn. Swoon is the oldest and the start of the trend, but Zak Pelaccio and Jori Emde’s Fish & Game is now the most prominent.

The compulsory prix fixe of the past is now gone, and the best way to approach this restaurant is by sitting in the barroom and snacking with a glass of house wine or beer. We did so and enjoyed wood-oven-roasted oysters, which remained liquid underneath a brown crust. Wednesday is pasta day, with a supplementary special menu. (Getting guests to eat at Hudson restaurants midweek is something of a challenge since many patrons visit the county mainly on weekends.) The wild mushroom and ricotta ravioli, with thickish wrappers, proved excellent.

Other places we tried in Hudson in the course of a week included Aeble, a new Scandinavian-inspired restaurant with a nifty outdoor seating area in front on Warren Street. The warm gougeres were magnificent, the chicken liver pate similarly so, while the pimento cheese with Triscuits was a misstep. The fried chicken was reminiscent of Pies ‘N Thighs.

Another newcomer to the Warren Street scene is Food Studio, which cultivates a relaxed ambiance in its deep and narrow storefront, into which sunlight streams in the early evening. An eggplant stir fry dotted with ground meat and slightly sweet was a favorite, the cocktails are strong but odd, and the frisee salad so copious two could share. The place flaunts its Vietnamese influences, but it’s difficult to put an actual Vietnamese meal together there.

And joining a couple other very ambitious pastry shops is Patisserie Lenox. A breakfast menu provides eggs and bacon, but you’re better off sticking with breakfast pastries.

Lake Taghkanic

As we zoomed out of town tired of hiking, touring, and eating, we made a last stop at what is probably the only body of freshwater in the county with a sand beach, Lake Taghkanic, with its own exit from the Taconic State Parkway. It offers a beach on the west side of the lake, a picnic area, and a concessions stand called Coppola between the two, all with magnificent views. The hamburgers and fries are exactly the kind of municipal lake park snack that Danny Meyer was seeking to evoke when he opened the first Shake Shack in Madison Square.

Here, the hamburgers are topped with white American cheese and optional serve-yourself condiments that include onions, pickle chips, lettuce, and fresh tomatoes. As at Shake Shack, the fries are seasoned with a thick crust. And the cheeseburger and fries eaten together — with your nostrils full of sun, sand, and spf 50 lotion — is an experience not to be missed.