Only 20 years ago, the quirky cultural haven of Hudson, New York would have been an unlikely candidate to become a far north weekend colony of New York City.

This small city, about 125 miles north of Manhattan and just across the Hudson River from the bucolic Catskills Region, had spent decades in a steady slide, settling into a largely unremarkable and economically-depressed backwater by the mid 1980s.  But before that, in the early 20th Century, Hudson was known as a centre of prostitution and vice, and even earlier still, just after the Revolutionary War in the early 1800s, the city’s main industry – whaling – was one that would hardly appeal to most modern urbane sensibilities. Whales were hunted in the Atlantic Ocean and brought by ship up the Hudson River for processing, a grisly business that is commemorated today with a cheerful cartoon whale symbol on the city’s street signs.

But Hudson did not become a quirky weekend destination by ignoring its sordid history. In fact, Hudson’s seedy past seems to add to its appeal.  And the town’s longstanding economic struggles led to a neglected Victorian-era housing stock that  attracted artistic types who have transformed the homes of whalers and hookers into boutiques, bed and breakfasts and antique shops.  

This transformation was immeasurably aided by the presence of an Amtrak train station at the base of Warren Street, the city’s main drag, from where most of the town’s attractions are within walking distance. This has proven an irresistible magnet for non-driving urbanites who can ride the rails for just more than two hours to leave the city’s crowds and malodours behind. 

And the magnetic pull is only gaining power, as this city of just under 7,000 people is steadily attracting marquee names.  In the past year alone, the artist Marina Abramovic announced plans to open an Institute for the Preservation of Performance Art in Hudson, designed by the acclaimed architect Rem Koolhaas; two chefs that worked under Wylie Dufresne at Soho’s WD-50 opened a restaurant called Crimson Sparrow; a steady stream of celebrities including Claire Danes and Harrison Ford have been spotted shopping and dining in town; and rumours persist that the hip Ace Hotel chain of Portland, Oregon, and New York City fame is eyeing properties in town.  City dwellers will also recognise Le Gamin Country, a casual French restaurant with original locations in Brooklyn’s Greenpoint and Prospect Heights neighbourhoods, and sections of Warren Street have Tribeca-esque names like BeLo3 (Below Third Street). 

But this emulation of all things New York City should not detract from the serious creativity that has taken root here. Basilica Hudson, an arts venue in a large 19th-century factory in a desolate area near the rail tracks,  looks at first like the perfect place to carry out a crime, but actually hosts a steady series of eclectic programming including contemporary art exhibitions, sewing workshops, classical music concerts and art film screenings. Time and Space Limited, located in a brick building that was once a bakery, hosts art exhibits, quirky theatrical productions and independent movies. Across the street, Helsinki Hudson, also located in a renovated factory building, offers a diverse schedule of established musicians from Shawn Colvin and Pete Seeger to bands that deserve to be better known, like The Big Takeover, a rock/reggae band.

Helsinki Hudson, which opened in 2010, is also a popular restaurant, serving satisfying Southern food like the beautifully plated Aunt Thea’s Fried Chicken in an upscale setting. And this is just one of many newcomers to Hudson’s particularly strong dining scene.

Café Le Perche, a bakery with a liquor license that serves breakfast, lunch and dinner, frequently sells out of its outrageously delicious croissants and chocolate chip cookies. Another restaurant bound to become a Hudson institution is the Chai Shop, where authentic Indian food made from local ingredients, such as wild spinach pakora, is served inside a still-functioning home furnishing store.  For more casual fare, the new Grazin’ looks like a greasy spoon but it is the first restaurant in the US to be certified by Animal Welfare Approved, meaning that the grassfed Angus cattle are humanely treated – and also make a delicious burger. 

Shopping is also a key attraction in Hudson, and Warren Street is lined with high end but cheaper-than-the-city antique shops, boutiques and art galleries. Check out White Rice for women’s clothing and home furnishing;  Rural Residence for antiques; Five and Diamond for vintage clothing; Carrie Haddad Gallery for contemporary art and photography; and The Spotty Dog for books and micro brewed beer.

The one area where Hudson is still lacking is in accommodations, so visitors should book rooms well in advance. The Inn at Ca’ Mea, attached to a well-regarded Italian restaurant  with a lively bar, has an excellent location right on Warren Street. Another good choice is the meticulous Croff House Bed and Breakfast. And though Hudson is incredibly walkable, a car will add to your options of places to stay.  About 17 miles away, the sleepy town of Hillsdale, New York, for example, has the elegant Inn at Green River and the affordable and modern Silvanus Lodge.

A car also opens additional options to explore the surrounding rural landscape. Most notably there is Olana, the historic home of the Hudson River School painter Frederic Edwin Church. There are guided tours available of his sumptuous, Moorish-style house that overlooks the Hudson River, and there is a network of trails and pathways to explore the 250-acre estate. 

If you arrive in Hudson without a car, Olana is still within reach. Since it is just under four miles from downtown Hudson, taxis are more than used to taking city visitors to the site.