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    5. Private 1-Hour Winery Horseback Ride Near Charlottesville
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    Private 1-Hour Winery Horseback Ride Near Charlottesville

    Private 1-hour horseback ride through vineyard and creek at Cunningham Creek Winery

    5.0 stars• 145 reviews
    From$159/ personincl. taxes and fees

    Duration

    1 Hours

    Includes

    Guided ride, Safety equipment

    Highlights

    Ride with your group and a guide on a private, walking-pace horseback tour at Cunningham Creek Winery. Follow paths through the vineyard and along the creek, then head to the winery after your ride for tasting and bottles.

    • Meet your guide for a private ride with just your party
    • Ride at a walking pace through vineyard and farm scenery
    • Watch for goats and pass by strawberry fields along the route
    • Finish the ride and make your way to the winery for wine tasting
    • Plan to tip your wrangler; 20% gratuity is customary
    • Confirm you have 4+ riders; tours require a 4-person minimum

    What's Included

    • Guide
    • Safety equipment
    • Helmet (available)

    Things to know

    Ages 12+; riders under 12 must have riding experience. Closed-toe shoes and pants are required. Alcohol and smoking are not permitted on rides.

    Cancellation Policy

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

    FAQs

    Yes. You need a minimum of 4 riders for this ride. If you don’t have 4 customers, the operator will reach out to reschedule.

    Wear closed-toe shoes and pants.

    No. Helmets are available, but not required.

    Meeting details

    Please meet us at Cunningham Creek Wine, 3304 Ruritan Lake Road, Palmyra, VA 22963.

    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 #WHE8JZ

    1.5 Hour Ride

    $159

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

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      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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