23.3 miles. Mostly flat rail-trail. Rolling hills in other spots.

The day begins at the Wassaic Metro-North station which is located right at the southern end of the Harlem Valley Rail Trail. This is a beautiful car-free trail that takes you through the fertile farms and historic towns of the Harlem Valley. You will, however, have to ride on a quiet rural road along portions of this ride, since there are gaps in the trail. There are rolling hills in this section. The route is entirely paved and there are various stores and services along the route, as well as historical markers which explain the history of this fascinating region.

To get to Wassaic, you can take Metro-North from Grand Central Terminal or from any stop along the Harlem Line to access the Wassaic station. The train leaves Grand Central at 7:47 a.m.

Once you arrive in Wassaic, we will meet you at the train station and give you a small “go bag” containing an energy bar, fruit and water to get you on your way. The rail trail begins right in the train station parking lot, so you are on  your way!  Lunch is “on your own”, but there are plenty of places to stop, including the quaint Village of Millerton, which is about halfway along the route. Millerton has a wonderful farmer’s market where you can help us pick out what local food to make for dinner.

The rail trail ends at Taconic State Park in Copake Falls where camp would be set up. Since you will likely have time before dinner, you have the opportunity to explore a lot of what this park has to offer. Highlights include a short hike to Bash Bish Falls, exploring the historic iron works or swimming in an abandoned ore pit. Also, if you want to do additional bike riding, the roads around this park are ideal to explore on your bike.

Once we are settled in, dinner would be served in the park’s picnic pavilion, where will be doing a cook-out. There is also a deli nearby as well as a bar, for those seeking to purchase other items or enjoy a game of pool and music at the bar.

46.7 miles. Rolling hills, mostly downward.

Day 2 starts with breakfast served at the campground. Then, after breaking down camp and stowing gear in the van, the ride begins westward towards the Hudson River riding back roads with very little traffic. This will be a longer and more challenging ride than Day 1, but you also have all day so you can take your time. While the terrain is hillier on Day 2,  the good news is that you are generally moving from a higher to lower elevation.  So for every uphill climb you encounter, the downhill on the other side is much longer. So you’ll be spending more time riding down hills than up.

Lunch is again “on your own” but you will have plenty of opportunities for breaks. Highlights include the historic Village of Red Hook as well as a potential swim at Lake Taghkanic State Park. After vaulting across the Hudson River on the Kingston-Rhinecliff Bridge, you’ll also have an opportunity to explore historic Kingston before turning south for the last few miles, winding along the Roundout Creek on your way to Rosendale.

Rosendale is a town once known for its cement plant. Today it is better known as a local artists community featuring an interesting main street located in a steep valley along the Wallkill River. Live music is usually offered somewhere in Rosendale on any day, including at the Rail Trail Café which is near our camping spot. 

Day 3 – Choice of route, ranging between 19 or 41 miles. Mostly flat rail-trail. Rolling hills in other spots.

Day 3 starts with breakfast at the campground. After we pack up, we ride up to the top of a massive train trestle…which is now the Wallkill Valley Rail Trail. After taking your pictures of the gorgeous valley beneath you, you’ll start riding south on this beautiful pathway. This trailway is not paved – it has a gravel/stonedust surface, which could have muddy spots in places after a rain. Riders using road bikes will be given an alternate route using roads if they do not want to take their bikes on this trail. Hybrid bikes and mountain bikes will have no problem on this relatively smooth, yet unpaved trail.

The shorter distances of Day 3 allow for time to explore things along the way. Highlights include the Village of New Paltz, which is an ideal place to get lunch (again “on your own”). They also have a pool nearby if you want to go swimming. Those looking to ride the shortest route will get to experience the fantastic “Walkway over the Hudson”, an abandoned railroad trestle which was converted into a walkway that takes you to Poughkeepsie (the endpoint of the short ride). The Walkway is extremely scenic!

Those looking to do a longer ride will have the option to add on a distillery tour, vineyard and wine tastings. (Additional costs apply) Participants can choose to do any combination of these.

•          Take a tour and enjoy a tasting at Tuthilltown Spirits, New York’s first whisky distillery since prohibition, and makers of Hudson Whiskey.
•          Visit beautiful Whitecliff Vineyard for a tasting of their wines. Whatever you buy, we will pick up and carry for you!
•          Have lunch or check out even more Hudson Valley products the Gardiner Liquid Mercantile for a region-wide tasting of beer, wine, spirits and ciders. Again, whatever you buy, we will pick up!

If you do these options you can ride over to Poughkeepsie and the Walkway Over the Hudson, or push on to Beacon and ride across the Newburgh-Beacon Bridge. Both places have numerous restaurants and stores if you are looking to grab a bite (or a beer) before heading home. We can also shuttle you from the last wine tasting stop to the train station if you cannot finish the ride.

When the tour is over, we will take whatever you cannot carry home  (including any wine that you buy) back to our offices where you can pick everything up later in the week. If you signed up for our gear pick-up service, we will deliver your gear back to your home the same day the tour ends.