Explore 400 years of history on a bike tour to Upper Shirley Vineyards. Engage in dialogue, enjoy wine, and support local conservation efforts.
Explore 400 years of history on a bike tour to Upper Shirley Vineyards. Engage in dialogue, enjoy wine, and support local conservation efforts.
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Upper Shirley Vineyards - The journey begins at Upper Shirley Vineyards, located just outside Richmond, VA. Here, participants will enjoy a tour highlighting the rich history of Charles City County and the stunning James River, also known as Yeokanta, famously referred to as The River Where America Began*.
Cycling along the dedicated Virginia…
- Upper Shirley Vineyards - The journey begins at Upper Shirley Vineyards, located just outside Richmond, VA. Here, participants will enjoy a tour highlighting the rich history of Charles City County and the stunning James River, also known as Yeokanta, famously referred to as The River Where America Began*.
Cycling along the dedicated Virginia Capital Trail, participants will encounter the inspiring and sometimes challenging truths of history. The tour will also look towards America’s future by introducing VCU’s Rice Rivers Center and their efforts in water quality and river health preservation. The ride continues to the Historic Westover Parish Church and grounds, established in 1730, where a comfort station is available. The route then leads back to the vineyard, which is situated on the original grounds of Historic Shirley, America’s oldest working farm.
After the trail tour, participants will gather at Upper Shirley Vineyards to enjoy a glass of wine and an optional riverside lunch, providing an opportunity to connect and reflect.

- Glass of wine from Upper Shirley Vineyards
- Stylish helmet, signature snack, bottle of water
- Comfortable, chic, 3 speed, Priority bicycle fitted with Nantucket bike basket and custom liner
- Experienced Guide
- Glass of wine from Upper Shirley Vineyards
- Stylish helmet, signature snack, bottle of water
- Comfortable, chic, 3 speed, Priority bicycle fitted with Nantucket bike basket and custom liner
- Experienced Guide
- Gratuities
- Gratuities
This bike tour offers more than just a pleasant ride through beautiful landscapes; it provides a chance to reflect on the past, comprehend the present, and contribute to a fairer and more equitable future. Participants will journey through 400 years of history, culminating at a modern vineyard to enjoy wine and celebrate friendships and shared…
This bike tour offers more than just a pleasant ride through beautiful landscapes; it provides a chance to reflect on the past, comprehend the present, and contribute to a fairer and more equitable future. Participants will journey through 400 years of history, culminating at a modern vineyard to enjoy wine and celebrate friendships and shared connections.
What makes this tour truly unique?
The tour delivers a balanced and nuanced portrayal of history, recognizing the complexities and contradictions that have shaped America’s identity.
It promotes open dialogue and respectful idea exchange, fostering shared understanding and empathy.
The tour emphasizes responsible travel practices that reduce environmental impact and support local communities.
A percentage of each tour is donated to local conservation groups such as Capital Trees, VCU Rice Rivers Center, and the James River Association.
- Outside food is not allowed at the vineyard.
- E-Waiver Required for each traveler - https://waiver.smartwaiver.com/v/basketbiketours/
- Booking requires a minimum of 4 people; once met, additional bookings of 1–10 are allowed (max 14).
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.