12 of The Best Fall Drives in The Hudson Valley and Catskills

Posted by Amy Wallace on Thursday, October 22nd, 2015 at 2:40pm

12 Best Fall Drives

Where can you get the best recommendation for a fall leaf peeping drive in the Hudson Valley and Catskills?

Hudson Valley and Catskills Real Estate Agents are the perfect resource for this! We spend our lives in our cars. It's our business to know the most beautiful spots on every country road.  So, some of us got together and discussed our all-time favorites, and we're sharing them with you. Have a great drive through our territory and stop in at any of our 6 offices to pay us a visit. If you're interested in passing by some properties for sale as you motor down any of these routes, just contact us and let us know which route your planning on taking. We'll give you the skinny on what you can drive by, or even meet one of us to take a tour!


Dutchess and Columbia County Fall Drive 

 "Dutchess County, NY is a prime spot for autumn leaf peeping. Located near the northwest corner of Dutchess County, it is home to descendants of the Livingston, Astor and Montgomery families, and the legendary Beekman Arms, America’s oldest continuously operating inn, from 1766. Rhinebeck boasts 35 miles of meadowland, streams and wooded hills with lovely mountain vistas across the Hudson River. From village Victorians to farms and pre-Revolutionary War homes, there are many quaint bed and breakfasts and a wide variety of  fine culinary destinations. Rhinebeck was selected as one of the Top 10 Fall Foliage Spots in the Nation by MSN.com."


From the Taconic Parkway, take Rt. 44 East to Millbrook.
Continue on Rt. 44 to Amenia.
North on 22 to Millerton.
Continue on 22 North
(a wonderful stop is at Bash Bish Water Falls, Route 344 East off Rt. 22, A quick 20 minutes walk from Parking area).
Continue on Rt. 22 North to Hillsdale.
Take Rt. 23 West to Hudson.
Take 9G to Rhinebeck and have a great Lunch or Dinner.
Take Rt. 308 east – chages to Rt. 199 back to the Taconic Parkway.

 Peter and Stella Ilani


Orange County Fall Drives

I've loved the drive along the "Hawk's Nest" on Route 94 since I was a little kid. I even remember this Porsche commercial form the 80's (this is a serious throwback). Below it is a recent amateur video taken recently during the fall. Amazing how much the quality of cameras has changed! But the beauty of this road hasn't. If you follow Route 94 all the way to Newburgh you can stop on the waterfront (Bluepoint is great) and have some lunch and then head on up the Taconic to hook up with Peter and Stella's route above." Becky Matta-Candela



In Orange County there so are many beautiful drives but two of my favorites are the drive on Route 302 into Pine Bush with a spectacular view of the Shawangunk Mountains off in the distance to your left, and the other is Orrs Mill Road...a country road shortcut from Salisbury Mills into Cornwall with a gorgeous view of mountains, valleys and the high in the sky Metro North railroad tressle!
- Nancy Warner


I've spent considerable time between Orange an Ulster County and lucky for me I've found a absolutely beautiful ride from New Paltz. Albany Post Rd through the quaint village of Montgomery and the across Rt. 416 to Rt. 208 into the historic village of Goshen. - Joan Lonergan




Ulster County Fall Drives


My favorite drive(s) in the Fall are going from New Paltz across "the Ridge" to High Falls via Mountain Rest Rd. There are beautiful wooded areas on both sides of the road on the first part of the drive that goes up to the entrance to the Mohonk Resort, and then as you start down the other side, there are spectacular views of the farmlands below plus the Catskill Mountains in the distance.

Another favorite is the route from New Paltz west on Route 299 past Wallkill View Farms where you see rolled bales of hay, cornstalks, and pumpkins in the fields waiting to be picked on the way up the Ridge, and then after connecting with Route 44-55 west, more spectacular views of the Catskills and the valley below on the way to Kerhonkson.

On a sunny October afternoon with the darker blue sky and clouds, and the sun shining on the falling leaves as I drive, it's a beautiful sight! - Cheryl Wherry

Karen Schneck agrees with Cheryl - here's her description of Cheryl's first route above.

I myself am a fan of the double whammy drive complete with iconic views of both the Shawangunk Ridge and Albert Smiley Memorial Tower atop and beautiful spread to the west of the Catskills:  From New Paltz, Exit 18 off of I87, turn left on 299 W.  Follow 299W over the Walkill River; bear right on Gatehouse road (second right after crossing the bridge) passing the historic Mohonk gatehouse on your left; park for a photo op or walk along the old carriage trail or alternately park down the road on Butterville to walk into the Mohonk preserve (if you plan to hike on the preserve Day passes are available at the Mohonk Visiotr's Center, assorted trailheads or memberships are available online); turn right on Butterville Road to four way stop; left on Mountain Rest Road up over the mountain for a gorgeous view of the Catskills; Mountain Rest turns into Mohonk road once you travel over the mountain; follow Mohonk Road all the way into High Falls; Turn left on 213 west for yummy food at the charming Luncheonette,  across the street at the quirky local institution, The Eggs Nest, or just down the block at The Last Bite.  If it's Sunday make a pit stop at the D&H Canal Historical Societies weekly flea market.  Continue down 213 W a short distance to cap off the afternoon with Pick-your-own apples at Mr. Apples on the left or a mile or two more down 213W on the right at, "ecologically grown, "Stone Ridge Orchards. - Karen Schneck


One of my favorite drives is Clove Valley Rd from Gardiner to High Falls.  It actually runs through the Mohonk Preserve with spectacular views of the usually “unseen” part of the Shawangunk cliffs.

My next favorite is High Point Mountain Rd from Samsonville Rd to Watson Holllow Road with some great views of the Ashokan Reservoir.

"I like observing from the top of the overlook trail in Woodstock, it’s a pretty hike to the top, and if you make it up the water tower the horizon is unbelievable, you almost see the earth bend in the distance. And if you like taking pictures the old abandon hotel and leaf peeping are its finest.

Here's a little tought on fall....

Losing the leafs, your disappointment won’t let you appreciate the trees, as they bear and shed themselves, there left more vulnerable. All trees possess natural beauty, all different yet the same, they reach deep into the earth, observe life- they stand tall and naked, sometimes fighting with each other creating the wind, there branches clanking like mating Antelope. Thru this process they show off their true colors and then sleep until they can start anew. “

Greene County Route 25 (just off Route 23C just after you pass through Haines Falls (heading West)  which runs through Onteora Park up in Greene County.   The vintage estates and vistas are fantastic to see.  At the top is the Arboretum with beautiful trees, landscaping, and gardens.  Definitely worth the trip.

Route 28 once you pass Phoenicia is very nice too.  Open mountain views that run along the Esopus Creek.  The Catskill Mountain Railroad runs leaf peeping tours on their vintage trains on most weekends as well.





 Greene County Fall Drives

Rt. 23 C West Jewett Center traveling westerly into Lexington and ending at Rt.  23 A Prattsville   You get to view the Phoenicia Notch and multi mountain ranges in either direction absolutely stunning


Can't not mention CR 20  "Designated Scenic Byway"  aka Cunningham Rd back side of Windham heading towards Albany the "back way"....  mind bending views of the valley, range and distant river views too- knock your socks off!  http://durhamvalley.com/scenic_byway.html



 Cunningham Rd, Durham> Magnificent views... jaw dropping, plus fabulous color.





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Amy Wallace - Marketing Director - Coldwell Banker Village Green Realty

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