Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /Things to do in Scottsville…
    3. /Land Activities
    4. /Horseback Riding
    5. /Private 1.5-Hour Horseback Ride in Keswick Vineyards
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Resources

    • Travel Guides
    • Experience Gift Cards
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Product image 2
    Product image 3
    Product image 4
    Product image 5
    Gallery image
    Gallery image 1
    Gallery image 2
    Gallery image 3
    Gallery image 5

    Private 1.5-Hour Horseback Ride in Keswick Vineyards

    Ride a private guided trail through Keswick Vineyards, then enjoy a complimentary glass

    5.0 stars• 156 reviews

    Duration

    1.5 Hours

    Includes

    Private guided ride, 1 glass

    Highlights

    Saddle up for a private, guided horseback ride at Keswick Vineyards, led at a walking pace. Explore wooded trails and vineyard views, then head back to the tasting room afterward.

    • Meet your wrangler near the tasting room and saddle up
    • Ride wooded trails and take in views of the Southwest Mountains
    • Pass the pond and look for the swans
    • Stop at the LOVE sign for a photo
    • End where you started, then make your way to the tasting room
    • Tip your wrangler after the ride; 20% gratuity is customary

    What's Included

    • Private guided trail ride
    • One glass of wine per rider
    • Safety equipment

    Things to know

    Minimum of 2 customers is required to run this ride. Ages 12+; riders under 12 must have some riding experience. Closed-toe shoes and pants are required; helmets are available but not required.

    Cancellation Policy

    Cancel 7+ days before for a 90% refund (booking fees non-refundable). Cancel 48+ hours before for a gift card. Full refund or gift card if the operator cancels due to weather or other unforeseen circumstances. No-shows or cancellations under 48 hours are charged full price.

    Product ID: QKJC97

    FAQs

    Yes. You need at least 2 customers for the ride to run. If there aren’t enough riders, the operator will reach out to reschedule.

    Wear closed-toe shoes and pants.

    No. Helmets are available but not required.

    Meeting details

    Keswick Vineyards

    Experience provided by Indian Summer Guide Service

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    1.5 Hour Ride

    $196.10

    For ages 12+, riders under 12 must have some riding experience

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    5.0
    Excellent
    156 reviews•Google Maps
    144
    0
    0
    0
    1

    Ashton and his team have built something genuinely special here, pairing horseback riding with some of Virginia's most scenic vineyard settings. Rides take place at locations like Veritas, Merrie Mill, and Pollack Vineyards, weaving through fields, forests, and wine country with views that reviewers consistently describe as breathtaking. The guides are a clear standout, patient and knowledgeable with beginners while keeping things relaxed and fun for more experienced riders. What comes through repeatedly is how well the team handles nervous or first-time riders. Multiple people mention conquering fears or being surprised by how comfortable they felt, which says a lot about the tone Ashton and his guides set. The horses themselves get high marks too, described as gentle, well-mannered, and obviously well cared for. Groups ranging from bachelorette parties to family outings all seem to leave happy, and many mention already planning a return visit.

    What people are saying

    Review 1 of 5
    5/5

    My wife and I had an extraordinary experience horseback riding through MerrieMill Farm and Vineyard. We had a private ride and our two guides were Riley and Cameron. They were professional, courteous, funny, and nice and made our experience that much better. We were on excellent horses which matched our experience and size. We rode on Bart and Barbie. The horses were beautiful and made sure our ride was easy and simple. Riley even stopped twice to take photos of the two of us. One photo will definitely go up on our wall of our travel photos. Many thanks to both Riley and Cameron and also to Ashton the owner.

    Photo of Eric Morris

    Eric Morris

    July 28, 2026

    Review 1 of 1
    5/5

    My wife and I had an extraordinary experience horseback riding through MerrieMill Farm and Vineyard. We had a private ride and our two guides were Riley and Cameron. They were professional, courteous, funny, and nice and made our experience that much better. We were on excellent horses which matched our experience and size. We rode on Bart and Barbie. The horses were beautiful and made sure our ride was easy and simple. Riley even stopped twice to take photos of the two of us. One photo will definitely go up on our wall of our travel photos. Many thanks to both Riley and Cameron and also to Ashton the owner.

    Photo of Eric Morris

    Eric Morris

    July 28, 2026

    Nearby activities

    Private Horseback Ride at Merrie Mill Farm & Vineyard
    Private Horseback RidesUp to 4

    Private Horseback Ride at Merrie Mill Farm & Vineyard

    Explore Keswick vineyards on a private guided ride with mountain views

    Explore Keswick vineyards on a private guided ride with mountain views
    5.0 • 156 reviews
    $196/ person
    Summer Sauna & Cold Plunge in Charlottesville
    Aromatherapy

    Summer Sauna & Cold Plunge in Charlottesville

    Wood-Fired Sauna, Cold Tubs, and Riverfront Community

    Wood-Fired Sauna, Cold Tubs, and Riverfront Community
    4.8 • 220 reviews
    $40/ person
    5-Hour Charlottesville Wine & Brewery Tour
    Wine Tours

    5-Hour Charlottesville Wine & Brewery Tour

    Build your own Charlottesville wine and brewery route with a private driver

    Build your own Charlottesville wine and brewery route with a private driver
    5.0 • 470 reviews
    $583
    Charlottesville Wine & Brewery Tour
    Wine Tours

    Charlottesville Wine & Brewery Tour

    Plan a private, driver-led tasting route through Charlottesville’s local drink scene

    Plan a private, driver-led tasting route through Charlottesville’s local drink scene
    5.0 • 470 reviews
    $424
    5-Hour Charlottesville Wine & Brewery Tour
    Wine Tours

    5-Hour Charlottesville Wine & Brewery Tour

    Choose your Charlottesville tasting stops and leave the driving to a private van

    Choose your Charlottesville tasting stops and leave the driving to a private van
    5.0 • 470 reviews
    $795
    Charlottesville Beer, Wine & Cider Tour
    Wine Tours

    Charlottesville Beer, Wine & Cider Tour

    Build your own three-stop Afton beverage outing with round-trip transportation

    Build your own three-stop Afton beverage outing with round-trip transportation
    4.9 • 229 reviews
    $74/ person