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    5. Private Winery Horseback Ride Near Charlottesville
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    Private Winery Horseback Ride Near Charlottesville

    Ride Chiswell Farm trails, then head to the tasting room

    5.0 stars• 145 reviews
    From$196/ personincl. taxes and fees

    Duration

    1 Hour

    Ideal For

    4 people

    Includes

    Private guided ride, 1 wine glass

    Highlights

    Saddle up for a private, guided horseback ride at Chiswell Farm & Winery, then wrap up back at the tasting room for light fare and wine.

    • Meet your wrangler and saddle up near the tasting room
    • Explore the property with Blue Ridge Mountain views
    • Ride at a walking pace with a knowledgeable guide
    • Return to the starting point and continue on to the tasting room
    • Follow ride rules including no alcohol or smoking during the ride

    What's Included

    • Private guided trail ride
    • One glass per rider

    Things to know

    Ages 21+ only. Minimum of 4 customers is required to run the ride. Closed-toed shoes and pants are required.

    Gratuity is customary; standard tip is 20%.

    Cancellation Policy

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

    FAQs

    You need a minimum of 4 customers for the ride to run. If that minimum isn’t met, you’ll be contacted to reschedule.

    Wear closed-toed shoes and pants.

    No. Helmets are available but not required.

    Meeting details

    Chiswell Farm & Winery

    Experience provided by Indian Summer Guide Service
    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

    Reference #F9NKB7

    Person

    $196.10

    For riders under 21+

    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
    145 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

    Had a tremendous experience, our guide was extremely knowledgeable and a great time to be around. Couldn’t recommend Indian Summer Guide Service enough!

    Photo of Stopel drewsky

    Stopel drewsky

    May 5, 2026

    Review 1 of 1
    5/5

    Had a tremendous experience, our guide was extremely knowledgeable and a great time to be around. Couldn’t recommend Indian Summer Guide Service enough!

    Photo of Stopel drewsky

    Stopel drewsky

    May 5, 2026

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