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Spooky Sleepy Hollow Three Day Tour + ADD NEW ROUTE


38   in New York New York204 Miles

By KerriOber
on November 1, 2007

2.8out of 5

6 Riders rated

 Scenery

 Road Quality

 Roadside Amenities

Written Directions

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.

Scenery

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..

Road Quality

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.

Roadside Amenities

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.

Additional Info

- View the weather forecast for this area from Yahoo weather.

Nickname (optional) : KerriOber

What Riders Say About this Route Add Review & Rating

By Guest
on May 7, 2009 2 out of 2 members found this review useful.

No Rating Provided

Motorcycle Year 2006

Motorcycle Make Harley-Davidson

Motorcycle Type Sport-Touring

Just for your information . Trucks have never been alound on the Taconic PKY. With that out of the way .The rides looks nice. I am planing to give it a try.

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By Guest
on July 11, 2009 1 out of 1 members found this review useful.

2.5out of 5

Motorcycle Year 2003

Motorcycle Make BMW

Motorcycle Type Sport-Touring

I don't know why anyone would want to visit Poughkeepsie, nor ride north on route 9 (other than its on the map and heads conveniently north). There's virtually no view of the Hudson, so better route is probably north on 82 after you pass Millbrook.....but then that's just me. Prefer countryside to driving through one town after another (rt. 9).

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By Guest
on February 6, 2008 1 out of 1 members found this review useful.

No Rating Provided

Motorcycle Year 1982

Motorcycle Make Honda

Motorcycle Type Other

In case you haven't checked recently, they don't allow "18 Wheelers" on the Taconic Parkway. It's PASSENGER CARS ONLY. And that hairpin turn on Rt. 2 has one of the best views I've ever seen! Later.

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By Guest
on June 23, 2013 0 out of 0 members found this review useful.

3.0out of 5

Motorcycle Year 2007

Motorcycle Make Harley Davidson Electra Glide Standard

Motorcycle Type Touring

Great ride but I found the time lines way out of wack..I did this ride in a day....I didn't do it 100% to the detail for several reasons...One I was already in Lennox, MA at the start and second I didn't like the Rt 9 leg at all..I got off Rt 9 on Rt 41 E (great decision) 10 miles of awesome road...picked up the Taconic parkway N and then got off on Jackson Rd East back to 7.....really nice ziggin and zaggin...All in all a beautiful beautiful day

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By Guest
on October 10, 2012 0 out of 0 members found this review useful.

No Rating Provided

Motorcycle Year 2010

Motorcycle Make Harley

Motorcycle Type Touring

I have had the pleasure to ride these roads many times and they are fantastic. The Taconic is a good ride north of NY 55...and commercial trucks are not allowed on this road....

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By Guest
on September 29, 2008 0 out of 0 members found this review useful.

No Rating Provided

Motorcycle Year 2006

Motorcycle Make Honda

Motorcycle Type Touring

The Taconic only allows cars / Motorcycles .Be carefull of the deer OCC has never been in the Dutchess county ..OCC is located in Newburgh.If you want Night life with a small town feeling with plenty of sites to see and places to stay...Go to New Paltz..Just accross the Mid hudson Bridge a little North from PK.....Lot of wonderful sites & historic land marks and alot safer at night. You will not regreat spending time there....

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