Spooky Sleepy Hollow Three Day Tour + ADD NEW ROUTE
38 in New York New York204 Miles
on November 1, 2007
- Trip Toolbox
Start your ride in Petersburgh, NY, just over the MA line at the meeting of RT 2 and 22. Take 22 South, and follow it all the way down to the hamlet of Millerton, which is in the gigantic town of Amenia. This is a long run along a fantastic scenic route through the foothills of the Berkshires. If you started the day at the beginning of this route, you'll be hungry. There's a cafe next to the movie theater in town, and a great pizza place. While in town, check out the glass blowing studio, and Saperstein's, which is an old fashioned dry goods store and a beloved Town Landmark. This leg of the trip will take you about 5 hours to make, so if you are done for the day, take 44 East into Lakeville, where there's tons of places to stay.
Otherwise, from Millerton, take 44 soutwest (she had east) to Poughkeepsie, and stay there. I'd suggest this, because it's a neat town, and one of the few places around here that doesn't roll up its sidewalks at 7 PM. Since Vassar College is here, there are lots of places to eat and stay in the vicinity.
In the morning, hop on 9 North, and go sightseeing at the Vanderbilt Mansion, the Mills Mansion, or the Old Rhinebeck Aerodrome. Somewhere along here is the OCC motorcycle site, if you happen to want to stop there to view gigantic egos at work.
Take 9 North until it meets with Route 23 in Hudson, New York. Take 23 East into Great Barrington, MA, where you might just want to stay for the night. Just South of town, on Route 7 is the Great Barrington Brewery, which serves some great food. There's tons of places to stay in, or just of town. In the morning, set out on Rt 7 North, another great ride, until it hits Route 2 in MA, and the ride's end.
Special note: I have an iron butt, and love long rides. You could pick out pretty much any section of this ride, and have a lovely time, though. If you are thinking of making a longer trip than a long weekend, look at my submissions for the Berkshires, or hook this trip up with a trip through the Adirondack State Park, just by getting on Route 22 North (it's SO Cool), and picking up on my directions in Comstock, NY.
The area covered by this ride is nestled between the Appalachian Mountain Range, and The Mighty Hudson River. This is Washington Irving Country, and there are many Dutch influences in the architecture, and the town names that you'll see. In the morning, because of the river and the mountains, there's often mist. Plus there's tons of covered bridges to see. Hit up coveredbridges.com to find them..
This route keeps you off the highways, and through mostly quiet towns. RT 22 can be very hilly, and twisty; so if that's not your thing, stay off it and get on the Taconic State Parkway heading North. Warning: the Taconic is known for speeding 18-wheelers, so stay out of their way. Also, RT 2 has a mighty steep hairpin turn right on the border of NY. If that isn't your cuppa, stay on 22, until you get to Route 9 in Hoosick, and take that to Bennington VT, and pick up on Rt 7 South, where you'll meet up with Rt 2.
I can't even list all the historic sites, spots to stop and wonder, and places to poke for antiques along this route. Also, additional roadside amenity information is included in the written directions below.
I do recommend before you start to fill your tank and bring snacks when you start the route. Rt 22 is lovely, but kind of sparse, until you hit Millerton.
I know Poughkeepsie is not an accepted international Hot Spot, but it's the best bet you have on this particular trip to walk around a decent sized town that has some interesting shops, eateries, and places to stay.
- View the weather forecast for this area from Yahoo weather.
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