Vineyard Rides


Experience the beauty and serenity of Albemarle County on horseback. Our 5-star private, guided horseback rides through vineyards and orchards in the Charlottesville, Virginia area is an experience unlike any other. Indian Summer Guide Service has built relationships with Charlottesville’s finest wineries, farms, and cideries in order to offer guests access to some of the most breathtaking properties in the region.

Hop on the saddle with your significant other, your family, or your friends – whoever you decide to bring, the experience is shaped around the desires of your group. Each of our private horseback rides is led by one of our knowledgeable guides, who will ensure your safety as well as your enjoyment. After the ride, make your way to the tasting room to enjoy locally crafted wines or ciders and stock up on your favorites.

We’re currently offering horseback rides at the venues listed below, each just minutes from Charlottesville. We can accommodate groups of 2-6 riders. Rides range from an hour to an hour and a half, depending on the venue you choose.  No experience is necessary. All riders must be in good physical health and weigh no more than 250 lbs. Rides are available daily and year round. Hours vary with each winery. The last ride will go out well before the tasting rooms closes, so you’ll be sure to get the full experience.

Contact us directly at 434-531-9679 to inquire about larger groups of 10 or more.

Glass House Winery 

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Explore 48 beautiful acres that include a winery, tasting room, lake with floating dock, B&B, glass house conservatory, and 12 acres of vines where several varietals are grown. Don’t even think about leaving without trying the chocolates!

5898 Free Union Road, Free Union, Va 22940     (434)- 975-0094     Open Th-Su 12-5:30 (and holiday Mondays)

King Family Vineyards

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Located in the foothills of the Blue Ridge mountains, King Family’s wines showcase the remarkable quality and terroir of Monticello Viticultural area.

6550 Roseland Farm Crozet, Va 22932     (434) 823-7800     Open daily 10-5:30 (Rides are not available on Polo Sundays)

Pollak Vineyards

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Family owned winery nestled in Greenwood, Virginia. Explore the beautiful property and expansive 27 acre vineyard on horseback.

330 Newtown Road Greenwood, Va 22943     (540) 456-8844     Open daily  11-5

Veritas Vineyard & Winery

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Enjoy the essence of Virginia and the wondrous beauty of the Blue Ridge in Nelson County.

151 Veritas Lane Afton, Va 22920     (540) 456-8000    Hours: Mon-Fri 9:30-5:30, Sat/Sun 11-5

Keswick Vineyards

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Nestled in a valley of rolling farmland and surrounded by the Blue Ridge Mountains, this ride will lead you through the beautiful vineyard, around the historic estate home and finish up at the rustic tasting room.

1575 Keswick Winery Dr. Kewsick, Va 22947     (434) 244-3341                Open daily 9-5

Cunningham Creek Winery at Middle Fork Farm

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Ride through the vineyard, meander down the creek, brush past the strawberry fields, watch the goats play and end your ride with a wine tasting.

3304 Ruritan Lake Rd. Palmyra, VA 22963     (434) 591-6666      Hours: Mon, Thu, Fri 11-6, Sat 11-6, Sun 1-6.

Castle Hill Cider

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Explore the historic grounds through meadows, creeks, orchards, ponds, and wooded trails. Enjoy a tasting of award winning orchard ciders upon your return.

6065 Turkey Sag Rd, Keswick VA 22947     (434) 296-0047     Hours: Wed – Mon 11 – 5

The Market at Grelen

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Experience the breathtaking beauty and serenity of Grelen nursery and trails. Casual cafe, event venue, garden shop, hiking trails, and PYO farm.

15091 Yager Rd, Somerset VA 22972     (540) 672-7268     Hours: Wed – Sun 11 – 4