Rails to Trails

A new stretch of the Rail Trail is underway which will connect the Highland and New Paltz trails. You may have seen them working on it near the thruway in New Paltz, NY. Soon you will be able to bike or walk from Dutchess County, across the Walkway over the Hudson River, out to New Paltz then north or south to Gardiner and our farm. Use our google map to help you plan your Highland adventure.

Closest to New Paltz is parking just past Lowes on the south side of route 299. On the other side of the street is Hard Roll Deli which serves breakfast and lunch sandwiches and salads. Boars head meats and cheeses, DIY salads, French fries, bacon egg and cheese all YUM. Indoor seating tables near the back or at the counter in the front. Plenty of snacks and drinks to take along your hike. If you get your food to go you can have a picnic along the trail, there are plenty of spots to choose from.

Follow the trail east you will go through recently opened tunnel and end up at Tony William's Field.

Tony William's Field has public basket ball, tennis, pickleball courts and a baseball field. Plenty of parking, restrooms and direct access to the rail trail.

There is a great playground for the kids. It is in the sun so on a hot day be prepared with sunblock, hats and waters. The slides sometimes have puddles if you want to be really prepared bring a towel or prepare to use your butt. There are two shaded pavilions that you could have your picnic in before continuing on the walk in the woods. The trail fortunately is mostly shade. Beware there is poison ivy along the woods, so if your dog goes on an adventure you might want to wipe him down before the kids cuddle him.

There is an entrance to black creek along this stretch of the trail. I guess you could launch your blow up kayak in it, but there is a better launch near the road. See our float your boat blog to learn more and where to rent. The steps that lead down to the creek are a good way to get your cardio going and work our those glutes. Kids will have fun looking for turtles, fish, frogs or maybe even some tadpoles this time of year.

If you have worked up an appetite there are a few nearby options in walking distance, but with kids it might be easier to drive. A little hot dog stand, Mark's Hotdogs. Mark is one of the nicest guys around. Don't let the idea of a hotdog cart scare you, these dogs are YUMMY and served from the cleanest conditions. Try the New Yorker!

Luigi's has yummy Italian sandwiches made by an old school Highland family. Be prepared to be on European time as owner Lou Olson serves you up some homemade meatballs and other sandwiches that represent what being a 2nd generation immigrant American Italian is all about. Bring your pooch and enjoy your lunch outside. Take home some pasta and fresh filled cannolis, BEST CANNOLIS in the Hudson Valley!

Do you need a pick me up and the kids need a treat? Visit Lakeside Lick's get a shake, soft serve ice cream or your favorite flavor of hard ice cream. There is outside seating to share with your favorite four legged friend. If the kids need some more excitement they can play a round of mini golf. This is the perfect place for dad to practice his putting skills.

If you are still walking on the trail heading east you will reach the Highland Rotary parking area. There you will find an old school train car that kids can climb on.

Depending on how much you want to walk you could always plan ahead and leave a car at each end. The rail trail has so many pretty views along the way take time to enjoy the

If you keep on walking you will end up in the Hamlet of Highland with plenty of yummy food, drink, and play options. And if you go even further you will reach the Walkway Over the Hudson, maybe there will be a moon walk by this time. Take the elevator down to the Poughkeepsie Waterfront for even more FUN.