League Operation

Softball games will be scheduled for Tuesday and Thursday mornings. Each team will play a single game per play date. The early games begin at 9:00 am while the later games begin at 10:30 am. Games are 7 innings with a time limit of 80 minutes. Game schedules are posted on this website along with game scores and current standings. Cancellations, rain-outs and other changes will be posted here as well (home page).

Each team will have a manager and one or more assistants. Managers will be responsible for creating lineups and making decisions during games. Typically managers communicate with their team members by email, text or other means as needed.

The league does not use paid umpires. Instead, teams will provide umpires from their rosters. Players from the other game(s) will be selected to umpire. Umpires are those who have been trained or will receive training before the season begins.

Divisions

WSSL teams are organized in two divisions.
  • The Yorktown Division (men 50 - 65; women 40 - 55) is a bit more competitive intense and players tend to be somewhat more skilled and mobile.
  • The Jamestown Division (men 66+ and women 56+) still plays competitive softball but in a less intense environment.
Each division will have 4 or more teams. There will be no inter-division games. Players may play in only one division, although it is possible that they might move from one division to the other during the regular season.

Calendar

Games in 2026 will be organized as a single season with a six-week break in mid summer. A player draft will occur in late March to form the teams. Prior to the regular season games, the latter part of March and early April is reserved for team practice sessions. Regular season games begin in early to mid April. Games end in late October, followed by two All-Star Games.

Schedule

The 2026 season will be conducted with teams of 12-14 players, depending on division. Normally, each team will play one game on Tuesday and another game on Thursday. On some weeks a team will have a bye and play only one game. Games will be either at 9:00 am or 10:30 am.

The season game schedule will be available as a PDF file as we approach the start of the season.

Rosters

Teams for the WSSL season will be formed in late March. Information on team rosters and managers will become available at that time.

Facilities

The Yorktown Division will play at Quarterpath Park, 202 Quarterpath Road, Williamsburg, VA 23185. The Jamestown Division will play at Kiwanis Park, 125 Longhill Rd, Williamsburg, VA 23185.

Both of these fields are maintained by Williamsburg Parks and Recreation. WSSL pays a usage fee for the fields. Note that alcoholic beverages are prohibited at both parks.

For a backup venue, we might also use the JCC Rec Center fields, 5301 Longhill Road, Williamsburg, VA 23188. The JCC fields are maintained by the JCC Department of Parks and Recreation. WSSL pays a usage fee for the fields. Note that alcoholic beverages are prohibited at these fields.
League-owned equipment will be available for transport and use at the fields. Included will be game balls, bases, plates, pitchers' masks, first aid kits and miscellaneous supplies. Players and teams are responsible for bringing their own gloves, bats and additional safety gear, such as shin guards.
Quarterpath Park
Kiwanis Park

Uniforms

The league will provide players with shirts and hats. Players are expected to wear these during games. Players may dress as they see fit for the optional practice sessions. All players will receive navy blue hats with the league logo on the front. Shirts will be provided in colors assigned to the various teams.

For Newcomers to Senior Softball

If you have played adult softball before but have not played in a senior league, you should know that there are some differences. To see the details, click the button below.