1 / 2Westchester Trail Rides
📍 Croton-on-Hudson, NY
Guided horseback riding on thousands of acres of woodland trails in Westchester, led by Cowboy Bob who specialises in beginner riders. Small group experiences on gentle, well-matched horses.
I drove from NJ to ride horses here with my daughter. Unfortunately, we arrived when the horses were eating haha so we waited half an hour for them to finish but they were still eating. The ride was supposed to last 1 hour but we could only tolerate about 30 minutes. The horse I rod on, Apache, was uncooperative however, Bob, helped to make him move! Bob was very nice and braved the 8 degree weather we were out in! I had a special request to ride before sunrise but so I am grateful he accommodated us.
🏆 Family Action Verdict
Best for families with older children or teens ready for their first riding experience. Cowboy Bob's patient teaching style builds confidence quickly on gentle, well-behaved horses. The woodland trails are genuinely scenic — not a paddock loop.
ℹ️ What to Know Before You Go
💬 What Families Are Saying
View all reviews →129 Google reviews
Nikkie Livee
a month ago
“I drove from NJ to ride horses here with my daughter. Unfortunately, we arrived when the horses were eating haha so we waited half an hour for them to finish but they were still eating. The ride was supposed to last 1 hour but we could only tolerate about 30 minutes. The horse I rod on, Apache, was uncooperative however, Bob, helped to make him move! Bob was very nice and braved the 8 degree weather we were out in! I had a special request to ride before sunrise but so I am grateful he accommodated us.”
Josephine
5 months ago
“It was such a pleasure visiting this place for the first time today. Cowboy Bob was our trail guide for my fiancé and I and took us around the trails in the woods, keeping in mind we are beginner riders. He was a great teacher, very welcoming, and the trails were beautiful. I would highly recommend!”
Grace A
6 months ago
“I wanted to spend some time in the woods with the horse, and was lucky to have found Cowboy Bob’s Westchester Trail Rides. It was just me and Bob on the trail—peaceful and lovely. Thank you, Cowboy Bob, for a lovely time. I felt incredibly lucky to have spent time with Buddy in the woods.”
Richie Shaw
4 months ago
“Had a wonderful time. Planned a special occasion and proposed to my long time girlfriend during the ride. Cowboy bob was amazing. Took us to a beautiful spot and took many amazing pictures. The horses were kind and gentile suitable to all riders. Will most certainly be going again”
Reviews from Google
Overview
Westchester Trail Rides runs guided horseback rides through thousands of acres of untouched woodland trails just 30 miles north of New York City. Cowboy Bob personally matches riders to horses, provides beginner instruction, and narrates the trail. The experience is small-group and peaceful, with guides happy to photograph special occasions. Multilingual guides are available.
