The seat of Dutchess County, Poughkeepsie was founded in 1683 and was designated the state capital in 1777. From the mid-1800s through the mid-1900s, the town was a major industrial center, serving as home base for IBM after World War II. But the late 20th century was not kind to Poughkeepsie. First, many of the factories closed down. Then urban renewal ravaged the city, replacing 19th-century brick buildings with stingy, low-slung edifices. Finally, in the 1990s, IBM laid off thousands upon thousands of employees.

Today, however, Poughkeepsie (Wappinger Indian for “reed-covered lodge by the little water place”) is in the midst of a radical upgrade. A $40 million waterfront project, which promises to revitalize the entire city, is under construction. Included in the project are a convention center, restaurants, shops, and a marina.

Downtown

Near the river and railroad station, where Union and Academy Streets intersect Main and Mill, are two bustling, restored historic districts filled with shops, pubs, and restaurants. Just up the hill from the restored historic district near the railroad station is the Cunneen-Hackett Cultural Center (9 and 12 Vassar St., 845/471-1221, 9 a.m.–5 p.m. Mon.–Fri., free).

The center occupies two handsome 1880s Italianate buildings built by the nephews of Matthew Vassar, the Poughkeepsie brewer who founded Vassar College. No. 9 now houses a small art gallery; No. 12 is home to another gallery and an exquisite Victorian auditorium—complete with gold-cushioned seats and stained-glass windows—where plays, concerts, and films are frequently presented.

The sloop Clearwater (112 Market St., 845/454-7673, www.clearwater.org) often docks downtown at the Main Street pier. Built by a handful of river-loving volunteers, Clearwater has been sailing the Hudson since 1969, bringing with it a message of environmental urgency. The vessel has been instrumental in helping to clean up the Hudson, and is the impetus behind the popular, three-day Clearwater Great Hudson River Festival, held in the region every June.

Entertainment

The county’s premier performing-arts venue is the Bardavon 1869 Opera House (35 Market St., 845/473-2072, www.bardavon.org). One of the oldest theaters in the country, it presents everything from top-caliber opera to serious drama. Two small but interesting professional theater groups connected with Vassar College are the New Day Repertory Co. (845/485-7399) and the Powerhouse Theatre (845/437-7235).

For live music, stop into The Chance (6 Crannel St., 845/471-1966), where nationally known artists playing everything from country to R&B perform. The weekend editions of the Poughkeepsie Journal contain good entertainment listings.