Today’s Route 209 closely parallels Old Route 209, reputedly the oldest highway in America. Originally known as the Old Mine Road, the old route ran between the copper mines near Pahaquarry, New Jersey, and Kingston  on the Hudson, and was built sometime in the early 1600s.
Many old homes and markers commemorating Indian raids are situated along Old Route 209, which runs concurrently with today’s route in many places.
About six miles north of Accord (take Rte. 209 north to Rte. 213 east) is High Falls, where the D&H Canal Museum (Mohonk Rd. off Rte. 213, 845/687-9311, www.canalmuseum.org , 11 a.m.–5 p.m. Thurs.–Sat. and Mon. and 1–5 p.m. Sun. June–Sept., call for off-season hours, adults $3, children $1) tells the story of the Delaware and Hudson Canal. Built in the 1820s, the canal was originally used to ship coal from the mines of Pennsylvania to the factories of New York. Later it was used to ship cement made in the High Falls area to New York City . In the museum are dioramas of the canal; working models of locks; and maps, photos, and artifacts.
Overlooking Lock 16 is the DePuy Canal House (Rte. 213, 845/687-7700, www.depuycanalhouse.net ), built in 1797 by Simeon DePuy. Once an inn, the two-story building is now a renowned four-star restaurant serving innovative American cuisine in an intimate setting complete with fireplaces, steep staircases, and wide floorboards. Request the eagle eye view of the kitchen to check out the chef in action via attic seating. Multicourse prix fixe meals are a popular choice here: $65 for five courses, $80 for seven. The Canal House also features a handful of cozy guest rooms in its Locktender Cottage ($100–225 d).
For a simpler meal, try the Egg’s Nest (Rte. 213, at Bruceville Rd., 845/687-7255, $7), an eccentric spot offering tasty sandwiches and soups or the artsy Northern Spy Cafe (Rte. 213, 845/687-7295, $8–19), which serves everything from burgers to Thai chicken with ginger.
Stone Ridge Orchard (Route 213, Stone Ridge 845/687-2587, www.stoneridgeorchard.com ), Davenport Farms (3411 US HY 209, Stone Ridge, 845/687-0051, www.davenportfarms.com ), and Mr. Apples (Main St., High Falls, 845/687-0005 www.mrapples.com ), all offer country fresh prepared baked goods, you-pick apple, raspberry and peach acreage, and farm activities like cider pressing or hayrides on busy summer weekends.
Bed-and-breakfast fans have two excellent choices in Stone Ridge. Bakers’ (24 Old King’s Hwy., 845/687-9795, www.bakersbandb.com , $98–138 d) occupies a 1780 stone farmhouse furnished with period antiques and a fireplace. All six guest rooms have private baths, and breakfast is served on a deck overlooking the Shawangunks .
The Inn at Stone Ridge/Hasbrouck House (Rte. 209 just outside the village, 845/687-0736, www.innatstoneridge.com , $195–425 d) is an elegant 18th-century Colonial mansion. It offers 10 guest rooms, an antique billiard room, 40 acres of gardens and woods, and a lake.
Off Route 209 on the outskirts of Kingston  lies a small village of 24 meticulously restored stone cottages similar to those found in New Paltz . Almost all are private homes open to the public only on Hurley Stone House Day (the second Saturday in July), but they’re still interesting to view from afar.
Hurley dates back to 1651, when French Huguenots built wooden homes along Esopus Creek. The settlers didn’t treat the local Esopus Indians as well as they might have, and in 1663, the Indians retaliated by burning down the Huguenot settlement. Six years later, the settlers rebuilt—this time in stone.
Self-guided walking tours of Hurley can be picked up at the post office at the town’s entrance, or at the Hurley Library or Elmendorf House, both on Main Street. A plaque with a town map also stands by the library.
The Elmendorf House, built in the late 1600s, is believed to be the oldest house in Hurley. Known as the Half-Moon Tavern in Revolutionary days, it now houses a small museum run by the Hurley Heritage Society (52 Main St., 845/338-1661, www.hurleyheritagesociety.org , 10 a.m.–4 p.m. Sat. and 1–4 p.m. Sun. May–Oct.).
Also on Main Street is the Polly Crispell Cottage, equipped with a “witch catcher,” or set of iron spikes set into the chimney. Just west of Main Street is the Hardenberg House, where abolitionist and evangelist Sojourner Truth, born a slave in Ulster County, spent her first 11 years.