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A few of the 10 bridges crossing the Delaware River between Sullivan County and Pennsylvania are listed on the National Register of Historic Places. None are more historic than the unusually-shaped Roebling Aqueduct, built in 1847 to carry the Delaware and Hudson Canal over the river. Today it still carries vehicle and foot traffic; it's been designated a National Historic Engineering Landmark as the oldest wire suspension bridge in continuous use in the U.S. Designer John Roebling applied what he learned here to one of his later projects, the Brooklyn Bridge. Even if you don't usually go out of your way to see historic bridges, this one is worth your time. It's managed by the National Park Service as part of the Upper Delaware Scenic and Recreational River, and worth the detour.
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On July 22, 1779, Patriot militia from Orange County bent on avenging a raid on what is now part of Port Jervis were decisively thwarted at this hill overlooking the Delaware River by British forces under the command of the legendary Iroquois leader Joseph Brant. Many of the dead lay there for 40 years before their remains could be retrieved. Today the site of the only major skirmish in the Upper Delaware during the Revolutionary War is a park with a memorial, interpretive center and trails that makes for a nice outing.
In the mid-2000s local entrepreneur Alan Gerry realized a long-held Sullivan County dream of capitalizing on the Woodstock festival site's potential as a tourist draw. The original site, at the southeast corner of the intersection of Hurd and West Shore roads, has been left undisturbed and accessible. On the hill nearby is a modern amphitheatre that has hosted performances by everyone from acts that appeared at the original festival to symphony orchestras. The nearby museum is also a must-see for anyone wanting to better appreciate the cultural significance of the surrounding acres of what was once Yasgur's Farm.
Located on the banks of Willowemoc Creek, this is an excellent introduction to the region's historic trout streams for both the experienced angler and the novice who'd like to give it a try.
Exhibits here are devoted to every aspect of fly fishing, with historic flies from the museum's extensive collection on display along with vintage bamboo rods and displays on Theodore Gordon and the others who made fly fishing what it is today while on the Catskill streams. They're changed regularly, so it's worth coming back. The museum's educational programs take advantage of its prime location on the banks of Willowemoc Creek, and offer something for everyone, from the novice to the seasoned angler and tyer who wants to explore rodmaking.