Weekend in Highland, New York: A secret gem in the Hudson Valley

When the Poughkeepsie-Highland Railroad Bridge was built in 1889, spanning 1.28 miles over the Hudson River in upstate New York, the local newspaper called it “the great connector.” More recently, the bridge was converted into the Walkway Over the Hudson State Historic Park, the world’s longest elevated pedestrian bridge.

“I still feel like it’s the great connector,” says Jami Anson, director of events for the Walkway. “It connects Ulster County to Dutchess County, and it connects people from all over the world.”

This weekend, we’re heading to Highland, which is set at the approach to the Walkway—just across the river from Poughkeepsie. Jami is one of our insiders who is going to help show what makes this little hamlet so special. She’s got quite the pedigree herself: Her roots in this area go back seven generations to the 1800s. “The best thing about Highland is the sense of community and closeness. Everyone’s a friend, whether you’re a stranger or not,” says Jami. “It’s got that welcoming, small-town quality that the Hudson Valley is known for.”

I felt that welcoming spirit myself when I brought my 10-year-old daughter and her Girl Scout troop on a recent getaway to Rocking Horse Ranch. This family-owned resort has been taking kids on trail rides since 1958—and helped put Highland on the travel map. Now, thanks to the Walkway Over the Hudson and a host of new businesses (cool cafes, restaurants, shops), the town is attracting the next generation of travelers.

One local entrepreneur making a splash is artist Amy Dooley: She recently opened Studio 89, a gallery and artist’s collective with a mural by NYC graffiti artist Lady Pink on its outside wall. She and her partner also own a local realty company, Hello Dolly Real Estate, that specializes in Ulster County homes. What she loves about this area: “It’s really beautiful and there’s a lot to do—from hiking trails to the river to music and culture,” she says. “Plus, there’s so much art in Highland and the surrounding Hudson Valley towns.”

Say no more: We’re on our way.

-Laura Begley Bloom, New York's Senior WeekEnder Writer

Whether you’re looking for an all-inclusive resort, a charming B&B, or a high-design Airbnb, you’ll find some good options.

This all-inclusive family-friendly resort keeps kids (and grown-ups) entertained for days, with horseback riding, mountain tubing, waterslides, laser tag, canoeing, bonfires, and more. The food is surprisingly delicious, especially the prime rib.

Within walking distance of the Walkway Over the Hudson is this B&B with gracious hospitality. “A beautiful little hidden nugget that feels like a museum,” says Jami Anson.

Surrounded by orchards and a golf course, Sam's Cottage on the Greens is the place for nature lovers and travelers who want to be close to the greens.

This two-bedroom Craftsman-style Airbnb rental is just steps from the center of town and has bikes for guests to use.

Highland is small but has a thriving food scene, with restaurants housed in historic downtown buildings, as well as destination dining spots scattered throughout the countryside.

The Baker’s Tale - Get there early. Everything is made daily from scratch—matcha tea scones, sourdough bread—and sells out fast. The specialty breakfast sandwiches are named after Hudson Valley locations like the Gunk Slammer, with eggs, cheese, and a hash brown patty on a brioche bun. Also good: “Her quiches are off the charts,” says Jami Anson.

The Restaurant at Apple Greens - Hidden away on a golf course with views of Mohonk Mountain House, this restaurant has seriously good dining, from morning to night. “It’s my favorite breakfast spot, though the sunsets at dinner are also beautiful,” says Jami.

Sal’s Place - “This has been around as long as my family has been here. It’s a down-to-earth community bar that is like Cheers, where everyone knows your name,” says Jami, who recommends the heroes and soups.

Pomo D’oro Pizza Cafe - Italian classics and creative pizzas like the Firenze (topped with herbed ricotta, marinated spinach, smoked bacon, mozzarella, and fresh tomatoes). “He has the best chicken Francaise I’ve ever had,” says Jami.

Hapág Bistro - “A small-town cafe with a small-town spirit and authentic Filipino food,” says Jami.

El Paso - This little Mexican deli is decorated with colorful murals. Amy Dooley recommends the shrimp tacos, while Jami is a fan of the egg salad.

Asian Garden - If you’re in the mood for Chinese food or sushi, this is the place.

Underground Coffee And Ales - A café, beer bar, coffee shop, and bottle shop with more than 100 different brews, ciders, and funky drink options that change weekly, as well as healthy pub grub. Think chicken pesto sandwiches and Buffalo Brussels sprouts.

Hudson Ale Works - This small-batch craft brewery serves beers made in house, plus Asian and Latin-inspired bites like chili-spiced Mexican pulled pork. “It’s a relaxed environment with games for kids and adults and a fire pit outside,” says Amy.

Gunk Haus Restaurant - This German-themed gastropub has killer views of the Gunks and sophisticated dishes like steelhead trout with grilled asparagus and sunchoke-cheese dumplings in a caper-dill sauce. “Beautifully prepared food and a lot of vegan, vegetarian, and gluten-free options,” says Amy.

Vigneto Café - Italian dishes are made with locally grown organic ingredients like the fan favorite: Chicken Vigneto topped with eggplant, sauteed spinach, marinara sauce, ricotta, and mozzarella.

Bad Seed Cider - This craft cidery is set on the family-owned Wilklow Orchards (which offers pick-your-own berries in the summer and apples in the fall). “The hard cider is top-notch,” says Jami.

DuBois Farms - An enticing spot with something for everyone: tractor-pulled wagon rides, animal petting, a farm market, a winery, pick-your-own fruits and veggies, and more.

Highland gives travelers easy access to the nearby Shawangunk Mountains and the waterfalls of Minnewaska State Park, but if you want to avoid the crowds there’s great nature to discover right here.

Walkway Over the Hudson State Historic Park - Take in the epic views from this 1.28-mile bridge that stretches from Highland to Poughkeepsie 200 feet above the river. As if the Walkway weren’t great enough on its own, there are events like Walkway at Night (held after dark on the first Friday of every month), music every Thursday, history talks, and more.

Hudson Valley Rail Trail - Walkers, joggers, and cyclists flock to this 7.1-mile pedestrian-only trail that connects the town of Highland to the Walkway Over the Hudson. “It has a canopy of trees like you’re in a magical forest,” says Jami Anson.

Franny Reese State Park - A 251-acre state park with trails and magnificent views of the Hudson River and Poughkeepsie. “A sleeper hit where you can have a really good hike,” says Amy Dooley. “Not that many people know about it.”

Bob Shepard Highland Landing - Take in the Hudson River breezes from this newly built waterfront park just below the Walkway over the Hudson.

Makers and artisans set the scene in Highland.

Studio 89 - This artist-run workspace gives local creatives a place to gather and share ideas, while visitors are invited to shop, listen to music, and get into the Highland vibe.

Knaus Gallery & Wine Bar - Is it a wine bar? Is it a cafe? Is it a shop? It’s all of the above. This gallery sells art and pottery, along with glasses of wine and light bites.

MayFest Makers and Farmers Market - On May 20 and 21, this massive two-day event on the Highland side approach to the Walkway Over the Hudson will attract more than 180 local producers (artisans, farmers, food producers, distillers, brewers), along with music and entertainment. In October, there’s a similar event (the Walktoberfest).

Gpa’s Bike Shop - Owner Mark Elia is a beloved local character and master charcutier who fixes up old bikes, is a professor at the Culinary Institute of America, and also has a catering kitchen out back. (You can try his barbecue and sausages at MayFest.)

Kiltmaker’s Apprentice - If you’re in the market for an authentic kilt, there’s no need to travel to Scotland: Bob and Doreen Browning make custom kilts and supply them to customers the world over.