Cycling Club

Ride, Dine, Imbibe, Repeat!

On Sundays, join cycling enthusiasts from The Williamsburg Winery team on a group ride through the Historic Triangle and back to the Winery for wine and brunch specials at the Gabriel Archer Tavern. We ride every Sunday (weather permitting) from March 17th-November 17th. There's no fee to participate!


The Williamsburg Winery Cycling Club is back and better than ever! We're beyond grateful for everyone's support over the last year; we've learned a lot and are excited for the year ahead. Due to feedback, both good and critical, that we've received, we're going to be making some enhancements this year. This is a group ride, and our expectations are that we ride together, with and for one another, making each ride fun, safe and enjoyable. Our rides will no longer be published as a "final average pace" instead; we will have groups designated by average "rolling" speed, meaning that we'll ride within that pace range on the flats, slower on the hills and faster on the descents. We'll also have "sprint zones" for those who want the challenge followed by designated meet up points. The purpose of our Club is to have fun, exercise, raise awareness for the world-class cycling experience in Greater Williamsburg, and most importantly, to make it back safe and sound so that we can enjoy great Virginia Wine, Virginia Craft Beer, and savor delicious local food. We hope you'll join us for many two-wheeled adventures this year. Cheers!

Sunday Group Ride Options:  
8:30 AM - Registration begins, refreshment station available
9:00 AM - Wheels up!

Option 1: Group will be riding 42 miles rolling between 18 - 20 mph. This route takes you along the Virginia Capital Trail to Brick Bat Road, left onto Centerville Rd and to the first entrance to Freedom Park,  to Jolly Pond Road and back to the Winery. No drop ride.

Option 2: Group will be riding approximately 30 miles along the Virginia Capital Trail rolling between 14 - 16 mph. No drop ride.


Discounts for Cyclists:

  • NEW! – All cyclists will receive 15% off wine only in the Wessex Hundred Retail Shop and Tasting Room following each ride. No other discounts apply.

  • All cyclists will receive 15% off food only at the Gabriel Archer Tavern following each ride. No other discounts apply.

  • After cyclists complete their 5th ride they will receive a Williamsburg Winery Cycling Club t-shirt.


Please join our Strava group: WILLIAMSBURG WINERY CYCLING CLUB 

Our rides will once again be supported by our good friends at Conte's Bike Shop of Williamsburg!

Helmets are required!

Will. Ride. For. Wine! 

Williamsburg Winery Cycling Club riders receive 10% off all repair services at Conte's Bike Shop of Williamsburg!  Our good friends at Conte's will be on-site every Sunday to assist with pre-ride adjustments and for post-ride pick-up and return repair services.  Post-ride repairs will not be done on-site at The Williamsburg Winery.  Repairs will take place at Conte's Bike Shop of Williamsburg and can be picked-up at the Shop or returned (no delivery charge) the following Sunday at The Williamsburg Winery.  For any questions about Conte's Bike Shop Repair Services please call  (757) 903-0702.

The Williamsburg Winery Cycling Kit by Hincapie Sportswear

Velocity Short Sleeve Jersey: $95*


  • 3 roomy back pockets provide plenty of storage for longer rides 

  • Full length hidden zipper

  • Hincapie Gel-Grip™ on elastic at back of waist to hold jersey in place 

  • ProGrip™ arm bands for enhanced comfort 

  • Comfortable raglan sleeves 



  • TourTek™ - A lightweight, moisture-wicking Lycra® fabric that moves with the body to provide the ultimate fit and flexibility. SunSmart™ technology is built into the fabric so it won't wash out; the fibers provide UPF 30+ protection of the harmful effects of both UVA and UVB radiation. 

  • ProGrip™ - Constructed of lightweight, laser-cut fabric, these bands feature a light silicone application to hold bands comfortably and securely in place against the skin. 

  • Hincapie Gel-Gripper™ - A flexible, non-slip strip that provides comfortable traction against any surface to help garments remain in place during activity. 

  • A polyester/Lycra® blended flat knit mesh with wide eyelet openings. This unique construction provides a combination of full coverage in a printable surface and excellent temperature regulation properties

Velocity Bibshort: $115*


  • Sublimated back panel is double-layered to prevent show-through 

  • Soft Diamond Mesh bib top 

  • ProGrip leg bands ensure garment stays in place 

  • Reflective tab out outer leg seams for added visibility in all conditions 

*Available in Mens and Womens style

Email Simon Smith at to place your pre-order now! 

Note: dates subject to change.

Find out more about our Overnight Cycling Packages

Located just 2 miles from the historic Colonial Parkway and just over 5 miles from the start of the renowned Virginia Capital Trail, Wessex Hundred is ideally located for cycling enthusiasts looking for a romantic wine getaway.

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© 2019 The Williamsburg Winery, LLC. All Rights Reserved.

The Williamsburg Winery
5800 Wessex Hundred
Williamsburg, VA


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November 1 - March 15

Sunday-Friday 12:00pm -4:30pm | Saturday 11:00am-5:30pm

March 16 - October 31

Sunday-Friday 12:00pm-5:30pm | Saturday 11:00am-6:30pm



Monday - Saturday 12:00pm - 7:00pm | Sunday 12:00pm - 6:00pm

Job Opportunities at The Williamsburg Winery