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Winchester Wheelmen


Winchester Wheelmen club rides


The Winchester Wheelmen offer group rides on Monday, Tuesday, Wednesday, Thursday and Saturday during riding season (typically March through October) for all levels of rider - so whether you are a beginner or a fast, ambitious rider you will find a ride to match your skill level. We allow the use of battery, pedal-assist e-bikes on group rides in Class 1 and Class 3. Class 2 bikes with a twist throttle are NOT covered by club insurance and NOT allowed on rides without exception  

Traditionally rides on Tuesdays and Thursdays are the most popular. Therefore we have ride leaders available on these days to offer rides at specific pace levels (typically 14mph, 16mph, 18 mph).  Ride leaders ensure adherence to the pace goal as well as regrouping efforts at pre-determined locations as well as major intersections. There is usually a “fast group” that will ride at their own pace without a dedicated ride leader.

Detailed information about all club rides (incl. Ride Leader contact details) can be found on the “Ride Calendar”

Please be ready to push off at the posted times - it is good practice to arrive 10-15 minutes early to allow ample time for a quick, final equipment check.

Note: Approved helmets are required for all rides. If you are not a club member, you must sign a waiver prior to the ride. Non-members may only ride one ride as a guest. Membership is a requirement following that guest ride per club LAB insurance requirements.

Photo Credit: Renee Lynn Photography

Ride Categories

To help participants identify an appropriate ride level for our members we have developed the following ride categories:

View Ride Categories

Beginner/Casual rides

If you are new to the sport - or try to get re-acquainted after a long hiatus there is a group ride just for you - Tuesday afternoons starting from White Post restoration. 

Tuesday Casual Group Ride – all WW club members are welcome to join us.

Begins April 2nd, 2024 at 6 pm (please be at ride location 10-15 min prior to 6 pm start).  Be sure to have a spring checkup for your bike prior to your first ride.  We’ll take a few minutes to talk about the rules of the road before we begin.  Helmets and lights/reflectors are a must!

White Post Restoration – 1 Old Car Drive- White Post, VA 22663

Our route will initially be a 6-mile loop.  Over the course of the season, we have several options for these casual rides. We will progress to an 18–24-mile ride as we get more comfortable with group rides in the beautiful countryside near Winchester.

Average riding pace is 8-10 mph- to 10-12 mph.  We will stop for rest and regrouping as needed.

Beginning July 2, 2024, we will ride from the 7-11 on Kimble Road in Berryville.  Please be at ride location 10-15 min prior to 6 pm start.  Beginning September3, 2024, we’ll ride at 5:30 pm for safety purposes.

Location:  Berryville 7-11 (north side of Rt 7) on Kimble Road and Route 7.  Please Park at the back edge of the parking lot.

Barbara Weber – ride leader- phone –(978) 390-4330 email-

Women only/specific ride

In 2020, a cycling initiative was organized to target women who wanted to improve their weekly mileage and serve as a network to increase interest in cycling camaraderie in the local Winchester area.

The ride starts from various locations during the week (Wednesdays) with a starting mileage of 17.4 miles with a goal to increase mileage or elevation gradually. This is not a beginner ride, we ride in two groups with targeted pace of 12-14 mph and 14 mph and above respectively. Ride leaders ensure adherence to the pace goal as well as regrouping efforts at pre-determined locations as well as major intersections. The faster group starts ahead ensuring everyone finishes together for some additional socializing time

We have planned the following ride locations (see Calendar for details): 1st-  beginning at White Post Restorations (White Post) and is a 17.4 mile with  700 feet of elevation- Ride begins on April 3rd  2024, - ends on May 29th

2nd  location will be at the 7-11 store and Kimball Road (Berryville) 21 miles- 482 feet of elevation. Ride begins on June 5st and ends July 31th. 

3rd  location is at Boyce elementary school (Boyce) 18 mile –  600 feet elevation. Ride begins on August 7thand ends on September 31 th

Paceline Ride

This is a hard-working paceline group with an expected pace of 20mph and greater. We use a relatively flat, 34 mile loop starting from a Berryville, VA location on Thursday evenings.

Photo Credit: Renee Lynn Photography


Mondays - Road Ride - Whitehall, VA

Distance: 25.3 miles

Elevation Gain: 1,350 ft.

Start: Ride from White Hall United Methodist Church, 3265 Apple Pie Ridge Rd, Winchester, VA 22603  - Google Maps


Push off time: 6:00 PM

Usually a casual ride to loosen up tired legs after some longer rides on the weekend.

Tuesdays - Road Ride - Stephens City, VA

Distance: 34.1 miles

Elevation Gain: 1,300 ft.

Start Location: Shop n Save Plaza east of Stephens City on VA 277 (380 Fairfax Pike, Stephens City, VA 22655). - Google Maps

Push off time: 6:00 PM


In the past, we have tried to structure this ride in different groups.  It has been very inconsistent and difficult to execute.  The result in 2024 is that there are typically two groups that show regularly: an A+ group that rides 21-23mph, and a B+ group that rides about  17-18mph.

There can be other groups that ride.  We ask that if you want to do this ride at less than 17-18mph to please post to the WW Google Group at   Or read postings from there for the same.  (As with all things, there is some "critical mass" needed to start a ride group.  Please share your intent or desire, as others have the same ideas.)

If you would like to be added to the WW Google Group to receive emails or make postings, please send a note to and you will be added.  The group is only for WW club members, but you are not added automatically as some club members do not want the automatic subscription.

Push is promptly 6:00 PM (18:00)

The ride meanders through two subdivisions and finishes at the Shop&Save parking lot after 34 miles.

Wednesday - Mixed Surface Ride

Distance: 22 miles

Elevation Gain: 1,310 ft

Start Location: Park at the Sherando Park Outdoor Fitness Gym, at Sherando  Park, off Warrior Drive in Stephens City.  Google Maps.  

Start time: 6:00 PM

Ride with GPS Link:

No ride leader. Pace determined by those who show up. Some steep hills (up and down) on gravel, but not too demanding. As per map, about 9 miles on gravel and dirt.

Women’s Ride 

Distance: 17.4 miles,

Elevation Gain: 700 ft

Start Location: White Post Restorations, 

Start Time: 6pm

This is a “women only ride” that will have two groups with designated ride leaders riding at 12-14mph and 14mph and above resp. average pace. Ride leaders ensure adherence to the pace goal as well as regrouping efforts at pre-determined locations as well as major intersections. The slower group will start first to ensure that everybody arrives back at the same time to allow for some additional "social time".

Ride location changes June 1.


Retired/Day-off Rides 

Start time: 10am/9am - depending on season

Start Location: Changes weekly - see Newsletter / Calendar for details

These rides are at easy to moderate pace starting at various locations which will be posted in the monthly newsletter Ride length is between 20 to 30 miles, with an average speed of 12-15 MPH. The rides usually have a lunch break stop or lunch after

White Post Ride

Distance: 17 miles

Elevation Gain: 700 ft.

Start Location: White Post Restorations, 1 Old Car Dr, White Post, VA  22663 - Google Maps

Start time: 6pm


As mentioned above ride leaders will be available for two differently paced groups - or you can just ride to your heart's content with the “A or B Team”. See the calendar for ride leader contacts.

As of April 5, 2022 we will offer to ride with a ride leader at either a 12mph or 15 mph average pace.  (Just a quick reminder that we are aiming for an AVERAGE pace - meaning that we will ride at higher or lower pace in sections of the route depending on terrain and traffic). Ride leaders ensure adherence to the pace goal as well as regrouping efforts at pre-determined locations as well as major intersections. Referencing our Ride Category Table these would be classified as B (15mph) or C+ (12mph).

These two groups will leave White Post Restoration parking lot approx. 2 minutes apart. The first 2 miles (10-15 minutes) will be ridden at a warm-up pace until we reach”Mile Marker 2” where we stop to regroup and ensure everybody is ok with pace etc.

Short stops/regroups follow at (or as needed):

Mile 5 at the intersection of Rockland Rd and Bowling Green Rd.

Mile 6.5 before we turn onto Rt 661 aka Fairground Rd.

Mile 9.7 after “1st climb”

Mile 13.5 at the Intersection of Red Gate Rd and Nelson Rd

Mile 14.5 Top of Hill in front of entrance to Longwood

Then we will make our way back to White Post to finish after 17.4 miles at the advertised average pace.

Total ride time for 12mph approx. 90 minutes, for 15mph group approx. 75 minutes.

Thursdays - Berryville, VA. - PACELINE

Distance: 32 miles - PACELINE

Elevation Gain: 800 ft.

Start time: 6:00 PM

Start Location: DG Cooley School,  Lower Campus, 34 Westwood Road, Berryville, VA 22611 - Google Maps


We have started this ride again for 2024. It is intended to have two groups:

Group 1: Slower group at nominal 18mph avg for the entire 32 mile loop. If you'd like to experience paceline in a controlled environment, this is the place to start. As point of reference, if you can self-pace at 15mph for 2hrs in the regional terrain, you can draft and participate in a paceline at 18mph. Safety and cooperation is very important in this ride. RE: No drinking with a rider directly behind you (wait until you rotate off the front for a drink) and no aerobars. There will be a modest warmup in this ride for about 15mins following push.

Group 2: For well-experienced paceline riders only. Pace is faster at 21-23mph (32 WW Paceline - Long). If you participate in this group, please familiarize yourself with the loop/map.

For both rides, push time is 6:00 PM (18:00) sharp.

This is at a school. There is no WC on the grounds. Please plan ahead. There are facilities within Chet Monet Park just to the west of the school, accessed from West Main Street (Business VA 7).


This is also a very good opportunity for anybody how is new to the sport, getting re-acquainted with cycling, getting back after an injury or simply wants to enjoy scenery at a casual pace. 

Depending on the group’s needs this ride can be shortened by using several shortcuts (anywhere between 6 and 12 or the full 17 miles).There will be another dedicated ride leader assisting the group in keeping pace and regroup (see above).

Saturday - Road Ride (aka the Shop Ride)

There are two Saturday morning shop ride loops. Both follow the same route until the intersection of Barley Lane and Middle Rd at mile 8.9.

Due to its popularity, participants usually form 2-3 groups at different levels. We have seen everything from a very casual pace to ambitious training groups. 

Start Location: Blue Ridge Bicycles, 2228 Papermill Rd., Winchester, VA 22601

Push off time: 8:00AM (May - September) & 9:00 AM (April & October)

Basic Loop: 20.7 mile ride


Added Distance Loop: 28 miles



Winchester Wheelmen METRIC CENTURY

Traditionally held during early October we organize a Metric Century ride for Members only. The event is fully supported with rest stops, breakfast at the start and lots of camaraderie. We also offer shorter rides to make the event accessible of all members - including families.

Ride time is 11:00 AM from White Post Restorations. Breakfast food will be there at 10:15 AM, and the ride will formally start at 11:00 AM. There will be a porta-potty present for everyones convenience.

Google Maps

Ride with GPS (RWGPS) maps have been updated for the day:

17.4 miles -

21.7 miles -

37.5 miles - (Rest area at Cooley School, west of Berryville, VA)

62.5 miles - (Rest areas at Cooley School and on Box Factory Road in Jefferson County, WV).

4th of July Ride

Another popular event is our 4th of July ride - usually around 25-35 miles at casual pace.

Thanksgiving Ride

Morning ride on Thanksgiving day to make room for the meals.

Winchester Wheelmen Google Group - Impromptu Rides

Our Google Group is very popular amongst members to arrange Impromptu Rides (mainly on the weekends). This is a great tool to meet with friends to exercise together. There is a ride posted almost every weekend with distances varying between 25-70 miles and usually moderate pace goals.

Visit Our Google Group

Winchester Wheelmen

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