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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• 137 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 (650) 414-7338

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    Reference #WHE8JZ

    1.5 Hour Ride

    $159

    0

    Why book through Greetwell?

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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
    137 reviews•Google Maps

    Indian Summer's guides clearly know how to make riders feel safe and comfortable, which comes through repeatedly in reviews. Ashton, Kathy, and Devon get called out by name for their patience, knowledge, and genuine care for both horses and guests. Several nervous riders mention conquering fears here, including one person who hadn't been on a horse in 13 years after being bucked off. The guides match horses thoughtfully to experience levels and take time answering questions, snapping photos, and adjusting to each rider's comfort zone. The Virginia vineyard settings at places like Veritas, Trump Albemarle, and Pollack deliver stunning backdrop rides that aren't the typical nose-to-tail trail experience. Groups with mixed experience levels do well here, and the horses like Gracie, JayJay, and Bo consistently get praise for being gentle and well-mannered. One cautionary note: there's a single incident where a guest experienced multiple spooking episodes with their horse and chose to cut the ride short due to safety concerns. This appears to be an isolated case among overwhelmingly positive experiences, but it's worth noting if you're particularly nervous about riding. Overall, this operation seems to strike the right balance between scenic adventure and attentive guidance.

    What people are saying

    Review 1 of 4
    5/5

    The mid-March ride we had at the Veritas Vineyard was incredibly picturesque, almost as though we were in a Thomas Kinkade painting. Being amongst the Blue Ridge mountains, the weather changed up on us last minute. Ashton, the owner, had clear and direct communication about timing & rebooking (due to potential inclement weather) up until the scheduled timeslot. Ashton & Riley were professional, knowledgeable, and well versed. They ensured that we had the most comfortable and risk-free ride possible. 5 stars no questions about it! ⭐️⭐️⭐️⭐️⭐️ We had a beautiful ride filled with pleasant conversation & laughs. After the ride we enjoyed a delicious wine tasting at Veritas Vineyard. Absolutely cannot wait for another ride with Indian Summer Guide Service!

    Photo of Veronica Torrez

    Veronica Torrez

    March 12, 2026

    Review 1 of 1
    5/5

    The mid-March ride we had at the Veritas Vineyard was incredibly picturesque, almost as though we were in a Thomas Kinkade painting. Being amongst the Blue Ridge mountains, the weather changed up on us last minute. Ashton, the owner, had clear and direct communication about timing & rebooking (due to potential inclement weather) up until the scheduled timeslot. Ashton & Riley were professional, knowledgeable, and well versed. They ensured that we had the most comfortable and risk-free ride possible. 5 stars no questions about it! ⭐️⭐️⭐️⭐️⭐️ We had a beautiful ride filled with pleasant conversation & laughs. After the ride we enjoyed a delicious wine tasting at Veritas Vineyard. Absolutely cannot wait for another ride with Indian Summer Guide Service!

    Photo of Veronica Torrez

    Veronica Torrez

    March 12, 2026

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