Catskill, the Greene County seat, sits on the sloping banks of the Hudson at the mouth of Catskill Creek. The natural harbor here helped the town grow steadily after its founding in the late 1600s. By the early 1900s, Catskill was the prosperous home of small knitting factories, brickyards, and distilleries.
During Prohibition, the town was known for its “retailers of liquid damnation.” Catskill applejack was brewed in the hills surrounding town and buried in jugs whenever the law came around. The lucrative moonshine trade coupled with the inaccessible hills made Catskill a favorite haunt of New York City  gangsters Legs Diamond and Vincent Coll. Diamond was once tried in the Greene County Courthouse, an imposing neoclassical building that still stands at the corner of Main and Bridge Streets.
Today, the town feels well worn around the edges, but retains a distinct charm. Besides the courthouse, Main Street showcases one big wooden building after another, many housing friendly old-fashioned businesses. Catskill Gallery (398 Main St., 518/943-3400, 10 a.m.–4 p.m. Tues.–Sat.), run by the Greene County Council on the Arts, presents exhibits, concerts, readings, and plays throughout the year. Running parallel to Main Street is Spring Street, a treasure trove of Victorian homes.
In the summer, check out the HI-Way Drive-In Theater (10769 State Route 9W Coxsackie, 518/731-8672, nightly May–Oct., $8 adults, $3 children 3–12, , show starts at dusk) which offers three screens and FM radio-generated audio for the double features shown nightly, complete with dancing popcorn and nightly games of chance during intermission.
The father of the Hudson River School, Thomas Cole lived in Catskill much of his adult life. Born in England in 1801, Cole came to New York City  in 1818. He taught himself to paint landscapes, and in 1825 took his first sketching trip up the Hudson. The works he produced on that trip won him instant recognition.
Cole’s former home, Cedar Grove (218 Spring St., 518/943-7465, www.thomascole.org , 10 a.m.–4 p.m. Fri.–Sun. May–Oct., adults $5, children under 12 free) is a big yellow-and-white affair with a wide veranda overlooking the Hudson. The house features exhibits on Cole and his family, other Hudson River artists such as Frederic Church, and the Catskills . Also on display are a few small works by Cole, and memorabilia such as his paint box and Bible. Out back is Cole’s old studio, housed in what were once slave quarters.
About four miles north of Catskill on Route 385 is the attractive village of Athens, first settled by the Dutch in 1686. At one time or another, the town has been a center for brickmaking, shipbuilding, ice-harvesting, and mushroom-growing (grown in the abandoned icehouses, after the advent of refrigeration).
Today Athens feels like a smaller and sleepier version of Catskill. Its streets, too, are lined with big old wooden buildings, many of them from the Victorian age, and the village hovers on an economic edge between neglect and gentrification. Route 385 south of Athens parallels the Hudson at water level, offering splendid views of the river and the 1874 Hudson-Athens lighthouse (518/828-5294, tours offered in summer).
Downtown, smack on the shores of the Hudson, is the Victorian Stewart House (2 N. Water St., 518/945-1357, www.stewarthouse.com; average dinner entrée $17, average bistro fare $11). Downstairs is a formal dining room and more casual bar/bistro area where contemporary American and French fare is served. Upstairs are five guest rooms ($100–125 d).