Horseback Riding Adventures in Upstate New York

Looking for a fun adventure? How about a horseback riding adventure through gorgeous trails in Upstate New York? Whether you’re seeking some solitude or a fun “family bonding” time, a trail ride is the perfect way to spend the day during a stay at the Caldwell House Bed and Breakfast. We’ve got some fantastic options below for horse lovers close by our home. Lessons, rides and more for all ages and abilities.

Ivy Rock Farms – New Windsor, NY – 6 minutes from our B&B – Owner, Shelley Gray, started Ivy Rock Farms 30 years ago with the goal to provide a facility that allows children & adults, from all walks of life, to enjoy horses safely, affordably and with excellent instruction. Take a 60-minute private lesson or one of their “learn to ride” packages. They also offer 90-minute or two-hour trail and gaming lessons. They provide professional and qualified instructors, volunteers and horses for all riders.

Twin View Stables – Campbell Hall, NY – 15 minutes from our B&B – Twin View Stables is a family run business that welcomes all ages and levels. Their gorgeous property is located on 60-acres of land on top of a hill that offers riders panoramic views and beautiful trails throughout the woods. They offer a wide range of services that includes lessons, training and trail rides and seasonal events throughout the year.

Juckas Stables – Pine Bush, NY – 30 minutes from our B&B – Offering scenic Hudson Valley horseback riding, Juckas Stables is a great place to go for a fantastic trail ride. Take advantage of their very popular 45-minute trail ride with an experienced guide who will take you around 117 acres of breathtaking farmland and trails. Their guides are experienced and knowledgeable equestrians, so you can rest assured you’re in good hands. They take time to get to know you, fit you to the right horse, and will give you the appropriate riding instruction so you feel safe and confident. The trail rides are mostly walking with occasional trotting only. Their staff will also help you take photos along the way! It is a fun adventure the whole family can enjoy!

Westchester Trail Rides – Croton-On-Hudson – 40 minutes from our B&B – Spend a day in Mother Nature! With acres of beautiful untouched land, enjoy a memorable trail ride with the folks at Westchester Trail Ride. They have a team of experienced guides to give you a ride with your family and friends that you will remember for years to come. Ethan Capshaw, known as “The Trailmaster,” knows every inch of the property and speaks four languages! Contact them for more information on rates for trail rides and anything else you need to know for a comfortable day on the trails.

You’ll be filled to the brim with a homemade, gourmet breakfast at the inn and then after a day on the trails, enjoy a relaxing dinner at one of our favorite local restaurants nearby. Our guests have enjoyed Blu Pointe, Bella Luna Ristorante Italiano, 1839 Restaurant and Bar, Liberty Street Bistro, and Loughran’s Irish Pub to name a few! Cap the night off with a game in our Living/Game Room, or with a book in our parlor. Book your getaay online today or contact us anytime with questions or for assistance booking your next Hudson Valley adventure!

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