About
Oswego Baseball & Softball Association Travel Baseball focuses on baseball and softball skills, including fielding, hitting, throwing, and base running. Kids take part in tryouts where these skills are evaluated in a controlled setting, and selected players go on to play a minimum of 30 games as part of their team. The program is part of a progression that also includes an Instructional (In-House) League and a Competitive (In-House Tournament Team) after the recreational season.
• Ages: 5–17 years old
• Schedule: Separate, multi-day tryouts for each age bracket in mid to late July; most teams hold light practices in the fall, then practice once or twice a week starting in January; the travel game season runs from April to July
• Price: Costs for 9U–14U teams are estimated at $1,400.00–$1,800.00; high school level teams (15U and up) pay OBSA operating fees of approximately $140.00; a first installment of $400 is due upon acceptance, with remaining amounts split into equal monthly installments
Oswego Baseball & Softball Association Travel Baseball is a program of the Oswego Baseball and Softball Association PONY Baseball, created to offer a higher level of competition beyond its in-house recreational program and intended for talented and motivated baseball players who are willing to commit significant time to improving their skills in a team-focused environment. Eligibility for the OBSA Travel Division requires players 13U and under to live within the boundaries of Oswego School District #308, while the boundary is open for 14U and above. Tryouts evaluate players on fielding, hitting, throwing, and base running, and selected players are called within 48–72 hours of the final tryout. Kids are evaluated each year and given feedback on strengths, weaknesses, and ways to improve.
Each team plays at least 30 games, and player fees cover items such as uniforms, field house and batting cage rental, field maintenance costs, league scheduling, umpires, tournament team fees, a batting helmet, a bat bag, miscellaneous team equipment, and third-party team instruction. Player fees do not include traveling expenses, personal equipment, or personal expenses, and fundraising and sponsorship opportunities are available to reduce player fees. Player fee details also note that the fee includes a batting helmet, bat bag, and miscellaneous team equipment, but not personal equipment.
Since 1989, the Oswego Baseball and Softball Association has focused on providing youth baseball and softball experiences for boys and girls of Oswego SD #308. The organization states a mission to provide an opportunity for children ages 5 to 14 to learn baseball and/or softball in a safe, welcoming, and instructive environment while fostering a love for the game, encouraging sportsmanship, teamwork, building confidence, and having fun. OBSA describes itself as a community-based, volunteer-centric organization that has exposed thousands of kids to baseball and softball, with leagues and facilities growing along with the community through active help from families and local businesses. The travel baseball program is led by OBSA’s Director of Travel Baseball, Jason Kudelka, with Dan Malloy listed as a contact for more information about OBSA.
Last updated January 14, 2026.
• Ages: 5–17 years old
• Schedule: Separate, multi-day tryouts for each age bracket in mid to late July; most teams hold light practices in the fall, then practice once or twice a week starting in January; the travel game season runs from April to July
• Price: Costs for 9U–14U teams are estimated at $1,400.00–$1,800.00; high school level teams (15U and up) pay OBSA operating fees of approximately $140.00; a first installment of $400 is due upon acceptance, with remaining amounts split into equal monthly installments
Oswego Baseball & Softball Association Travel Baseball is a program of the Oswego Baseball and Softball Association PONY Baseball, created to offer a higher level of competition beyond its in-house recreational program and intended for talented and motivated baseball players who are willing to commit significant time to improving their skills in a team-focused environment. Eligibility for the OBSA Travel Division requires players 13U and under to live within the boundaries of Oswego School District #308, while the boundary is open for 14U and above. Tryouts evaluate players on fielding, hitting, throwing, and base running, and selected players are called within 48–72 hours of the final tryout. Kids are evaluated each year and given feedback on strengths, weaknesses, and ways to improve.
Each team plays at least 30 games, and player fees cover items such as uniforms, field house and batting cage rental, field maintenance costs, league scheduling, umpires, tournament team fees, a batting helmet, a bat bag, miscellaneous team equipment, and third-party team instruction. Player fees do not include traveling expenses, personal equipment, or personal expenses, and fundraising and sponsorship opportunities are available to reduce player fees. Player fee details also note that the fee includes a batting helmet, bat bag, and miscellaneous team equipment, but not personal equipment.
Since 1989, the Oswego Baseball and Softball Association has focused on providing youth baseball and softball experiences for boys and girls of Oswego SD #308. The organization states a mission to provide an opportunity for children ages 5 to 14 to learn baseball and/or softball in a safe, welcoming, and instructive environment while fostering a love for the game, encouraging sportsmanship, teamwork, building confidence, and having fun. OBSA describes itself as a community-based, volunteer-centric organization that has exposed thousands of kids to baseball and softball, with leagues and facilities growing along with the community through active help from families and local businesses. The travel baseball program is led by OBSA’s Director of Travel Baseball, Jason Kudelka, with Dan Malloy listed as a contact for more information about OBSA.
Last updated January 14, 2026.
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