Signature Rides at Upper Shirley Vineyards

Signature Ride

Departing and ending at Upper Shirley Vineyards, enjoy a leisurely, 14-mile, guided bicycle tour along the Virginia Capital Trail.

March-December, Wed-Sun. $135 per person.

Petite Signature Ride

Shorter version of our Signature history/nature/wine tour. 6-mile, guided bicycle tour of the Virginia Capital Trail.

March-December, Wed-Sun. $115 per person.

Both tours include:

• Guided tour filled with stories of Virginia and American history, nature, and viticulture

• Comfortable, chic, 3 speed, Priority bicycle fitted with Nantucket bike basket and custom liner

• Stylish helmet, signature snack, bottle of water

• Glass of wine from Upper Shirley Vineyards

• Wed-Sun. 10am-1pm Signature Ride. 10am-12pm Petite Ride (allow extra time after for wine and optional lunch)

• Optional: Dine after your ride at Upper Shirley Vineyards Winery Restaurant. Prepay with us or purchase onsite. Veranda, patio, and indoor seating are available but fill up quickly on weekends. We recommend bringing a blanket or chairs for setting up your own spot on the lawn by the river. No outside food allowed.

  • Prepay add-on lunch options (includes service, tax, gratuity). From $35.

    • Lunch on the lawn

    • Reservation inside with additional grazing board

    • Simple and Chic picnic setup

    • Ask us about an upgrade to a specialized picnic setup (great for anniversaries, reunions, birthdays, bridal)

Contact us if you’d like to reserve a private tour, or would like your entire group (6 or more) to upgrade to RVA on Wheels Pedego electric bikes.

Our ride begins at Upper Shirley Vineyards, just outside Richmond, VA, with a tour devoted to the history of the Charles City County area and the beautiful James River, aka Yeokanta, that has rightly been called The River Where America Began*. Three nations came together to form this country we know as America—from early English settlers, who created a new nation of freedom on the shores of this river, to the Africans who arrived in chains to bear the brunt of the work in building the industries of cotton and tobacco, to the Native American Algonquins who already called this home some 15,000 years before.

As we pedal through cotton fields and past plantation land of Westover and Berkeley, we will face the inspiring and often uncomfortable truths of our history. We will bring in America’s future, introducing you to VCU’s Rice Rivers Center and their work on water quality and preserving the health of all rivers. We will bike on to a quest at Historic Westover Parish Church and grounds, established in 1613 and still in use today. We pedal back to the vineyard on what was once the original grounds of Shirley Plantation, American’s oldest working farm, to be reminded, this history is our story, and the truthful telling of it, our legacy. 

Rising up from the same ground where tobacco once grew, there is now a vineyard. After our tour along the trail, we will come together at Upper Shirley Vineyards to offer you the chance to connect over a glass of wine and riverside lunch. We will have wheeled our way through 400 years of history to a modern vineyard for wine and celebrating good friends and shared connections.

*Note:  The River Where America Began:  A Journey Along the James is also the title of a book published in 2007 by Richmond native, Bob Deans.

$5 of each rider goes to support our conservation and community partners: Capital Trees, VCU Rice Rivers Center, and the Virginia Capital Trail Foundation.