Cycling Club

Please know that the team and family at The Williamsburg Winery is well aware of and tracking all developments related to the current events surrounding novel coronavirus COVID-19.

To help all continue to enjoy life, while also staying healthy and safe, we have made some adjustments to our operations, including postponing the Cycling Club ride scheduled for Sunday, a new date to be determined. We are so pleased to have a large group of dedicated cyclists to enjoy the beautiful Williamsburg area. Of course, with a large group comes safety concerns, and we have made the decision to follow the current guidance recommended by the federal government to avoid gatherings of 10 or more people to provide for adequate social distancing. It's up to each of us to flatten the curve of the novel Coronavirus and protect our community.

If you need to get outside – which we all should do for our health – please know that our Wessex Hundred farm property and its 400 acres (surrounded by another 2,000 acres of farms and federal parkway) remains open to all. This is one of the huge things that we can do for our community – offering a dose of fresh air free from pollution. Come and walk, hike, run, bike, sit. You do not need to be a customer, just come enjoy.

First Official Ride of the Season – TBD

We're excited to get the 2020 Williamsburg Winery Cycling Club series season rolling!  I've updated below the description on the page to include the changes for the upcoming season.  This description includes information about the ride options with mileage, pace, distance, etc. We will be offering two group ride options this year.  


We are proud to continue the partnership with Hincapie Sportswear by offering discounts to our club members. I have the honor of serving as an Ambassador for Hincapie Sportswear this year. 


Registration – 8:00AM - 8:50AM

Ride Route & Safety Review & Group Photo - 8:50AM

Wheels Up  - 9:00AM (Group A will depart first followed by B+ Group)


Join us at the Gabriel Archer Tavern for Brunch specials every Sunday after the ride and receive 15% off food only ! Also 15% off wine only at the retail shop located directly across from the tavern following each ride (no other discounts may be applied)


Ride Options

Option 1: A pace  - 42 miles with a rolling speed of 19-21 mph. 

(Regular Group Leaders: David Lassiter & John Lyons)


Option 2: B+ Pace  - 42 miles with a rolling speed of 17-19mph

(Regular Group Leaders: Simon Smith & James Clark)


We will offer a C ride option at certain rides throughout the year, this will be posted on the WW Cycling Club Facebook page.

We truly appreciate the support for the club, a huge thank you also to the ride leaders that ensure our safety and keep the ride rolling at the posted pace! 


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.


Join us for a group ride on September 20, 2020 beginning at the Williamsburg Winery! Cycling enthusiasts of all abilities are invited to join us for a ride through beautiful James City County, followed by an afterparty on the Wessex Lawn featuring live music from the Sammy Lee Trio, grill out favorites, and a raffle to win prizes such as an overnight stay at Wedmore Place, tickets to the Hincappie Gran Fondo, and more! Each ticket includes the ride, rest stops, lunch, a glass of wine, and a ticket to be entered into a raffle drawing. Must be 21+.

Ride Details 
Four groups will be available for varying levels of ability, each guest may choose the ride option that best suits their ability. All routes include a rest stop at Chickahominy Park, offering food, water and restroom facilities. Located at 1350 John Tyler Hwy, Williamsburg.

Registration begins at 8AM at the Williamsburg Winery, the ride begins at 9AM. A refreshments station and a Trek bike pre-adjustment area will be available. We suggest using a road bike as it is the best option to ride in groups. You can also ride a mountain bike, touring bike, or single speed (with two brakes). Triathlon bikes, Recumbent bikes, Tandem bikes, trailers and bike seats are not allowed for safety reasons. Helmets are required.

We highly encourage all participants to know basic safety and bike repair skills, including fixing a flat tire. Be prepared and bring your own pump and extra tubes for your bike. However, if you are still unable to make the repair, group leaders will be following all ride routes and can assist you with any minor mechanical issue you may have.

Ride Options  
8:00 AM - Registration 
9:00 AM - Wheels up!

11:00 AM - Afterparty

25 miles C Pace - 11-14mph rolling speed with Route GPS link

45 Miles B Pace - 15-17 mpg rolling speed with Route GPS link

60 Miles B+ Pace -17-19 mph rolling speed with Route GPS link

60 Miles A Pace - 19-22 mph rolling speed with Route GPS link

After Party Grill Out!

After returning to the Williamsburg Winery, enjoy an after party on the Wessex Lawn! From 11-2PM, enjoy live music from the Sammy Lee Trio, a glass of wine, and a delicious lunch. A cash bar will offer local beer and a signature cocktail.  In addition to the cash bar, our friends from Big Island Aquaculture Oysters will have a half dozen of their locally grown oysters available for purchase. The raffle drawing will take place at 1:30PM, winners must be present to collect prizes. 



Local Virginia Burger with Pimento Cheese

Garlic Aioli | Heirloom Tomato | Arugula | Local Cheese & Grilled Potato Salad. 


Edwards Sausage Grinder with Shishito Peppers

Caramelized Onions | Smoked Paprika Sour Cream | Grilled Potato Salad


Caprese Sandwich with Pesto

French Baguette | Arugula | Tomatoes | Balsamic Reduction | Side Salad


Alewerks Brownie Sundae 


Grilled Donut Bar

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 

Helmets are required!

Will. Ride. For. Wine! 

Cycling Club Special Event!
September 20, 2020
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.

  • Facebook Social Icon
  • Twitter Social Icon
  • Google+ Social Icon
  • Pinterest Social Icon
  • Instagram Social Icon
  • YouTube Social  Icon

The Williamsburg Winery
5800 Wessex Hundred
Williamsburg, VA



© 2020 The Williamsburg Winery, LLC. All Rights Reserved.

If you need assistance in viewing or accessing our website, please call 757-229-0999 ext. 190.

TASTING ROOM HOURS - Temporarily Closed; Wine Pavilion Open May 15

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



Daily 12:00pm - 5:00pm - Temporarily Closed

Job Opportunities at The Williamsburg Winery