With Milford being located in the Tri-State area, rides in Pennsylvania, New Jersey, and New York are all within reach. Some days, all 3 states are incorporated in local rides, like Sunday, when we rode through each state with a Point Peter climb. But Tuesday was all about New York. Western Orange County has many beautiful roads. The roadway is well paved, the homes are stately, and the scenery is second to none.

I met up with Kyle at Action Bikes and Outdoor in Milford, and we pedaled down Rt.209/ Rt. 6 towards Matamoras. We veered left onto Mountain Avenue, hammered down to the Delaware River, and continued over the Port Jervis Bridge. Once in New York, we rode through the small river city, over to Port Jervis High School, and out onto Rt. 209 towards Middletown. This section of 209 is flat and fast. There is a narrow shoulder, but it’s enough to ride safely. As soon as you pass the horse farm on the right and Neversink Drive, go another mile and Peenpack Trail is on the left.

Peenpack is a nicely paved road that snakes up and around some well groomed country homes. You climb up Peenpack for about 4 miles, before dropping down across Rt. 42 and back up to a left hand turn on Old Forestburg Road. You basically just fly down until you reach Rt. 42 again, and make a right, pedaling another half mile you hang a sharp right onto Wilson Road.

Wilson immediately sends you back uphill, steeply at first but leveling out before capping the hill and flying down to Rt. 97. There, you make a right, and start the climb up to the Hawk’s Nest. Every 1/4 of a mile or so, there is a pull off that allows you some of the most breathtaking views of the Delaware River Valley. The road twists and turns for a few miles with a long descent back into Sparrowbush, NY. A right hand turn onto Sleepy Hollow Rd. puts you along the river and through Port Jervis’s West End neighborhood.

We cruised over the Port Jervis Bridge and back into Matamoras, PA. While pedaling along the PA side of the river, I realized how lucky we are to be able to ride in so many cool places and over such diverse terrain. After left a onto Mountain Avenue, we cooled down as we rode back into Milford.

Although the elevation gain is not terribly high, this is a difficult ride as it requires extremely good bike handling skills. The downhill sections are steep, and wind around corners before coming to sudden stops. Use caution whenever riding on Rt. 97.  A blinking red taillight alerts drivers that your sharing the road.