Formerly a village hall and jailhouse, this historical building is now home to one of Nyack’s most-loved restaurants. Although you won’t run the risk of being locked up, you’ll find yourself never wanting to leave – thanks chiefly to its Mediterranean-inspired menu and spritely atmosphere. Expect to dine on Berkshire pork chops served on a bed of white beans, chorizo and fennel, alongside classic strip steaks and fresh oysters with horseradish granita.

Roundhouse’s floor-to-ceiling windows that look directly out over the Fishkill Creek waterfalls, you’ll find it hard to draw your eyes away from the view – but trust us, the food will do a fine job of distracting you. The menu is ever-changing but has a distinct American focus; barbecue flavors are a fixture, with staples like hickory smoked chicken, beef brisket and ribs with all the trimmings. If the weather permits, dine outdoors on the patio next to the falls.

Upstate New York might not be a destination you think of as a leading American wine region, but it is in fact home to America’s oldest winery, Benmarl Winery, and a range of award-winning vineyards. Wine growing in the region dates back to as early as the 17th century, while Benmarl Winery was started in the 1800s by Andrew Jackson Caywood, before being bought by the Miller family in 1957. Stop by to get a taste for this history and its selection of wines; the rosé comes highly recommended.

Holding the title of the world’s longest elevated pedestrian bridge, the Walkway Over the Hudson is a must-visit while on a trip upstate. At a length of about 1mi (2km), it offers a decent workout if you walk or jog from one side to the other – but while doing so, take in the panoramic views of the Hudson River below. The walkway was constructed in 1889 as a railroad bridge, so visit with a guide to take away a history lesson too.

This Scandi-style space with its exposed concrete walls and blonde furniture is exactly the kind of restaurant you’ll wish was your local neighborhood spot. The restaurant serves up an Italian menu of antipasti like fritto misto and stracciatella on freshly baked bread, alongside a range of pastas and pizzas like spaghetti vongole and pepperoni pizza drizzled with chili honey.

You’ll find the design-led Hotel Kinsley in a former bank between the Catskill Mountains and the Hudson River. Revived at the hands of lauded interior designer Robert McKinley, this place has all the honeypot items that attract the well-heeled – like sumptuous Turkish rugs, a Farrow & Ball color palette and mid-century furnishings. Chuck in an uber-chic restaurant that serves an American-accented menu – highlighting local produce with dishes like New England clam chowder.

The Hudson River is hard to miss, flowing from north to south through the state of New York – and it acts as the beating heart of upstate New York, with many towns built on its banks. Dedicate some time to exploring it from a boat, soaking up the sun as you take in the river’s history. Your guide will narrate the significance of the cultural sights as you cruise past.