Trail Rides in the Wild West

  • All experience levels are welcome

  • Riders must be 8 years or older

  • Maximum of four riders per group

  • All trail rides are by appointment only

  • Ride times: 9 AM, 11 AM, 12 PM, and 1:30 PM

  • Rides are not confirmed until a credit card is on file and a confirmation email has been received

  • A 20% gratuity will be added to all trail ride bookings and goes directly to your wrangler

  • Closed-toe shoes are required for all riders

  • Riders should arrive 15 minutes prior to their scheduled ride for safety briefings

  • Weight limit: Riders must weigh under 220 lbs to ensure horse and rider safety

  • Helmets are provided and required for riders under 18. Helmets are optional but recommended for adult riders

  • Cancellations must be made at least 24 hours in advance to avoid a cancellation fee

  • We reserve the right to cancel rides due to inclement weather for the safety of our horses and riders

  • Fill out the trail riding form below and we will be in touch soon!

Trail Riding at Long Hollow Ranch

  • 1 - Hour Trail Ride

    1 - Hour Trail Ride

    $129 per rider

    Embark on a guided ride through the open landscapes of Sisters, Oregon, aboard our calm, well-trained trail horses. Our experienced wranglers focus on safety, comfort, and a relaxed pace, making this experience enjoyable for riders of all levels.

    To maintain a personalized and intimate ride, each group is limited to a maximum of four riders.

    A 20% gratuity will be added to all bookings and goes directly to your wranglers.

  • Wine N' Ride

    $379 per rider

    Enjoy a 2-hour guided ride through the high desert trails, taking in the wide-open landscapes and historic paths of our 130-year-old ranch. With time to slow down and connect, you’ll have the opportunity to bond with your horse and fully take in the experience.

    Upon returning from the trail, unwind with a curated wine tasting and a thoughtfully prepared charcuterie board on the porch of our Ranch House, overlooking rolling hay fields.

    A 20% gratuity will be added to all bookings and goes directly to your wranglers.

  • Ride & Reel

    $449 per rider

    Enjoy a relaxed 45-minute trail ride out to our private, fully stocked pond. Once you arrive at Two Pines Pond, spend up to two hours fishing, exploring, or simply unwinding in this quiet, scenic setting.

    We provide fishing poles, bait, trail snacks, and non-alcoholic beverages so you can settle in and enjoy the experience. Catch and release trout, bass, or crappie, then mount back up for a peaceful ride back to the ranch.

    A 20% gratuity will be added to all bookings and goes directly to your wranglers.

  • Trail Ride + Picnic Lunch

    $249 per rider

    Enjoy a 2-hour guided trail ride with a relaxing lunch break at our private Two Pines Pond.

    Midway through your ride, you’ll dismount and enjoy a quiet, scenic setting while taking in the views and slowing down for a true ranch experience.

    Lunch includes a freshly prepared sandwich, chips, fruit, a cookie, and bottled water. Meals are ordered fresh for each ride. Please let us know of any allergies or dietary restrictions when booking.

    Special lunch requests may be accommodated for an additional fee.

    A 20% gratuity will be added to all bookings and goes directly to your wranglers.

  • 1.5 - Trail Ride

    $189 per rider

    Enjoy a scenic 1.5-hour trail ride along the Long Hollow Ranch ridge, featuring sweeping views of the surrounding landscape.

    Your wrangler will guide you to a picture-perfect overlook and capture a photo of you on horseback so you can take a piece of the experience home with you. Photos will be shared with all riders following your ride.

    A 20% gratuity will be added to all bookings and goes directly to your wranglers.

  • Wrangler Experience Add-On

    Wrangler Experience Add-On

    +$75 per rider (add-on to 1-hour trail ride only)

    Step into the boots of a wrangler with this hands-on experience. Guests will spend additional time catching and grooming their horse, followed by a 30-minute arena session to learn foundational riding skills before heading out on a 1-hour trail ride.

    This add-on is designed for those wanting more one-on-one time with their horse and a deeper connection to the riding experience. Perfect for kids, beginners, or anyone looking to slow things down and learn more.

    Available exclusively as an add-on to the 1-hour trail ride.

    A 20% gratuity will be added to all bookings and goes directly to your wrangler.

Fill Our Our Trail Riding Questionnaire!