This route fills my desire for vast open skies and rolling hills. I start on the Kingston-Rhinecliff Bridge heading east into Dutchess County. The first left takes you to County Route 103, a scenic two-lane road which skirts by Poet’s Walk Park, where Washington Irving reputedly came up with the idea for “Rip Van Winkle.” The road leads us through the grounds of Bard College, whose stately stone buildings are in sharp contrast with Frank Gehry’s ultramodern Fisher Center for the Performing Arts.
From here we turn left onto Route 9G, and views of the Hudson and Catskills appear. Continuing north we approach the Rip Van Winkle Bridge, then head east to Route 82.
Now we are in real farm country, full of barns, horse farms, silos, vegetable stands, antiques stores — and open skies. After passing Lake Taghkanic State Park, I head west on Route 199, then connect with Route 308 to Rhinebeck, stopping for a cup of coffee at Bread Alone or skizza at Gigi’s Trattoria. Making a right turn, we’re back on Route 103, also known as River Road. This stretch is lined with beautiful and historic houses — one of which is Astor Courts, where Chelsea Clinton tied the knot in 2010. From time to time I enjoy exploring the many side roads in this area. The main route becomes the starting point as I weave in and out; in a way, it is a metaphor for my adventures in life.
For a longer ride, you can continue south on Route 82 to Clinton Corners, then make your way west back to Route 103.
Route 9G features great views of the Catskills as it heads north of Tivoli. A patriotic barn is another notable sight in northern Dutchess.
Dutchess Loop Directions:
- Cross the Kingston-Rhinecliff Bridge heading to Rhinebeck.
- Turn left onto County Rte 103 and continue for five miles.
- Turn left onto Rte 9G.
- Continue on Rte 9G for seven miles until you reach the Rip Van Winkle Bridge.
- Turn right onto Rte 23 heading east.
- Continue for 15 miles.
- At the intersection of Rte 23 and Rte 82, continue onto Rte 82.
- Travel for 30 miles, passing Amcram and Pine Plains.
- Continue west on Rte 199 for five miles until it connects with Rte 308.
- Travel through Rhinebeck for five miles.
- Turn right onto River Rd.
- Cross the Kingston-Rhinecliff Bridge.
- Enjoy your ride!