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    1. Local experiences/
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    4. Horseback Riding/
    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• 137 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 (650) 414-7338

    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
    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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