See the Clintons with One of the Best Westchester Bike Trails

The hottest time of the year is not the most ideal to be riding bicycles over a rather hilly region, but it beats doing it in the coldest time of the year! We at the Stanton House Inn still believe that bicycling is the best way to see our town and other towns near Greenwich CT. You can take your time, you can stop when and where you like, and if you take-up a wide enough berth in the road, car drivers will just passively-aggressively resent you rather than sideswipe you or honk! Here’s an opportunity to enjoy one of the best Westchester bike trails through beautiful Westchester County, New York.

westchester bike trails to see fall colors
Although if you wait until the fall, you’ll get sights like this! Generally, peak leaf-peeping here is late October and early November.
Credit: Paul Robinson/Flickr

For this suggestion for visitors looking for great Westchester bike trails, we were thinking a tour of the Hudson River Valley, the hills and inland towns and villages of upper Westchester County, and finally backcountry Greenwich before arriving here at the Stanton House Inn. As with the previous tour of the Gold Coast of Connecticut, one of the best parts is that the tour begins and ends near train stations on the Metro-North rail line for easy accessibility for those who don’t want to deal with a car (or don’t have one).

Westchester bike trails to see the Croton Falls
This is pretty cool, right?
Credit: Jon Dawson/Flickr

Westchester Bike Trails along the Hudson

First, take a ride up the Hudson Line of the Metro-North train system from New York City (heading towards Poughkeepsie) to the Croton-Harmon train station. Croton-on-Hudson is a beautiful little town right on the Hudson River with parks and plenty of activities, including the Clearwater’s Hudson River Revival Festival. The Alexander Hamilton House is a lovely little inn on a cliff overlooking the Hudson River in-town. You can check-out their website (and make reservations) click here.

Westchester Bike Trails through Chappaqua

After a night in Croton-on-Hudson, bike down to Ossining before heading into the hills above the Hudson and heading towards Chappaqua. Does this hamlet sound familiar? It should, it’s the current home of the Clintons as well as other notables such as Governor Andrew Cuomo. The Old Chappaqua Historic District is on the National Registry of Historic Places, and I hear both the Inn and restaurant at Crabtree’s Kittle House are pretty good. To check-out the Crabtree Kittle House Inn’s rooms or restaurant,click here.

Westchester bike trails go by beautiful fall foliage
I know all the pictures are Autumn, but doesn’t it look spectacular!?
Credit: WalkingGeek/Flickr

Westchester Bike Trails in Bedford NY

When you’re ready to move-on from Chappaqua, you can bike through the farms and residences of Bedford, New York (stopping-in to Bedford wouldn’t be a bad idea, either) until you reach Roundhill Road, which leads down into Greenwich. There are a lot of gorgeous homes (both mansions and old historic farmsteads) and forests along this way, including some beautiful ponds, lakes, and streams (just don’t drink out of them). Follow Roundhill Road until it ends near North Maple Avenue, which you can then follow down to Maple Avenue and find us here at the Stanton House Inn.

The best part of this trip is you get to avoid paying these ridiculous prices for gas! Well, not the best, but a nice part.
Credit: Alan Light/Flickr

Alternatives to Westchester Bike Trails

This bike trail will take almost three and a half hours if you biked it directly from Croton-on-Hudson to Greenwich in one sitting, but as with any trip getting there is half the fun. For those who don’t want to face the uphill trip from the Hudson River Valley inland, there’s a train station on the Harlem Line in Chappaqua, as well.

So check-out our map (which we created on Google maps) and see why we think this would be a great way to spend a long weekend, or maybe even a week!

And for even more recommendations on things to do in Westchester County or things to do in Greenwich CT, be sure to download our free Vacation Guide!