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ABOUT US
Founded in March of 2017 and incorporated as a 501(c)(3) public charity in March of 2019, Hillside Connection (HC) was established to “leverage the game of basketball to create pathways to opportunity for kids in Southern Colorado Springs.”
Beyond Basketball: A Year of Impact at Hillside Connection
At Hillside Connection, basketball is just the beginning. In 2025, we continued our mission of leveraging the game of basketball to create pathways to opportunity for kids in Southern Colorado Springs, serving over 1,000+.
Through intentional programming, strong partnerships, and deep community roots, we served youth and families across multiple districts—on the court, in classrooms, and throughout the community.
Our work is guided by a 5-Tiered Approach that ensures every young person has access to quality sports development, enrichment, competition, and support no matter where they start.
| | "HC ROOTS" - 2025 REAL IMPACT STORIES | | EVENT & PROGRAM SPOTLIGHTS | |
Hillside Annual Ball
Saturday, September 27, 2025
US Olympic & Paralympic Museum
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Hillside Connection proudly hosted the 3rd Annual Hillside Ball: A Night of Gratitude at the stunning U.S. Olympic & Paralympic Museum bringing together supporters, partners, and community champions for an evening centered on impact, connection, and purpose.
From delicious food and flowing drinks to a high-energy auction, the night was filled with excitement and generosity.
The program inspired and moved the room. Our keynote speaker, former Denver Bronco player Nick Ferguson, shared powerful reflections on perseverance, failure, and purpose. We were also deeply moved by our Youth Speaker, Gulong Craft, a State Track Champion and senior at Harrison High School, whose words embodied what is possible when opportunity meets support. Community leaders echoed that message, reinforcing a shared commitment to advancing our mission.
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Derrick White Signature Camp
Sierra High School
Saturday August 2, 2025
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Hillside Connection was honored to partner with Derrick White, Olympic gold medalist and NBA star for the Boston Celtics, for a powerful day of basketball, mentorship, and inspiration.
Derrick White teamed up with Hillside Connection to host a camp serving 100+ youth from Southeast Colorado Springs. Over five hours of instruction, athletes participated in skill development drills, competitive play, and meaningful conversations centered on work ethic, confidence, and believing in what’s possible. The camp was supported by 35 dedicated volunteers, helping ensure a high-quality, engaging experience for every participant.
Beyond basketball fundamentals, the camp provided our youth with rare exposure to elite-level leadership and positive role modeling. For many participants, this was their first opportunity to learn directly from a professional athlete which is definitely an experience that left a lasting impression both on and off the court.
We are grateful to Derrick White and Coach Mason for investing in our community and to every volunteer, partner, and family who helped make this day possible. Opportunities like this continue to advance our mission of leveraging basketball to create pathways to opportunity for youth across Southern Colorado.
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Dan O'Brien Speed and Agility Camp
Harrison High School
July 11, 2025
| | More than 35+ HC youth athletes showed up ready to run, learn, and grow at the FREE Speed & Agility Clinic with Gold Medal Olympian Dan O’Brien. Big appreciation to our partners U.S. Olympic & Paralympic Museum, TrueSport, Harrison High School Track & Field Harrison School District 2, Olympic City USA and all the youth and families who made this day unforgettable. Movement Mentorship Olympic Inspiration. That’s how we build something bigger than sports. | | | |
UCCS Holiday Camp
December 2025
Sixty-five Hillside Connection participants received a special invitation and scholarship to participate with Coach Jeff Culver and the UCCS Men's Basketball team at the Annual UCCS Holiday Camp.
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Winter Basketball Shooting Clinic
Hillside Community Center
November/December 2025
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This winter, Hillside Connection wrapped up an impactful Winter Shooting Clinic, serving over 150 youth participants from across Southern Colorado Springs. Each week brought high energy, focused instruction, and intentional support creating a well-rounded experience that developed athletes on and off the court.
To support youth through long training days, participants received weekly nourishment box lunches from Subway, Jersey Mike’s, and Bubba’s 33. These meals ensured athletes stayed fueled, focused, and ready to compete removing barriers and reinforcing the importance of proper nutrition.
Each session also included enrichment experiences that reinforced wellness, teamwork, and character:
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Yoga with Cambio Yoga, led by experienced instructors, helped athletes build flexibility, balance, and mindfulness tools that translate directly to performance and overall well-being.
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Teamwork and character presentations from TrueSport and USA Figure Skating challenged youth to think about respect, effort, and integrity both in sport and in life.
More than a clinic, the Winter Shooting Clinic reflected Hillside Connection’s commitment to holistic youth development combining skill-building, nourishment, enrichment, and mentorship in a safe and inspiring environment.
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9th Grade Transition Brunch
Hillside Community Center
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We celebrated our 9th graders; we are proud of their hard work and excellence thus far and encourage them to continue and grow beyond. This was not farewell; the HC family will be engaged with these kids every step of the way!
We invite these participants to stay connected via enrichment opportunities and give back as volunteers or coaches.
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CSD11 Spring Hoopster Basketball League
May 2025
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The CSD11 Spring Hoopster League launched its inaugural season in Spring 2025, marking an exciting milestone for expanding access to youth basketball in Colorado Springs. In its first season, 5 elementary schools participated, impacting 60+ 4th and 5th grade youth through structured, school-based competition.
This inaugural league reflected Hillside Connection’s commitment to putting youth and families first, creating opportunities that build confidence, teamwork, and school pride. We are grateful to the schools, coaches, families, and partners who helped bring this vision to life and look forward to the continued growth of the Hoopster League in the seasons ahead.
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HSD2 Fall Hoopster Basketball League
September - November 2025
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Hillside Connection and Harrison School District Two collaborated for a fourth season of elementary hoops in the heart of Southeast Colorado Springs! We're proud to partner with HSD2 to foster teamwork, community and school pride. Our goal is to help BUILD COMMUNITY and SCHOOL PRIDE to a struggling youth sports culture in Southern Colorado Springs. Every kid deserves access to quality sports programming!
THE HOOPSTER EXPERIENCE
- Over 200 4th/5th-grade boys and girls attended tryouts
- 13 Elementary Schools united | 16 teams | 200 participants
- Over 50 games played
- 2,000+ Attendees
- 26 Coaches Total | $700+ Average Stipend Per Coach
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Positive Coaching Alliance Preseason Coach Workshop
- Divisional play, championship tournament, jerseys, certified officials, and Nike basketball sneakers provided at no cost.
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7th Annual Boys 3V3 Basketball Tournament
Hillside Community Center | Memorial Park
| Hillside Connection’s Boys 3v3 Tournament brought energy, competition, and community together throughout Summer Jam 2025. Across six days of play, 55 youth participants competed in fast-paced games that emphasized teamwork, sportsmanship, and skill development. Supported by 35 volunteers, the tournament created a fun and competitive environment where athletes were challenged to grow both on and off the court. The Boys 3v3 Tournament set the tone for Summer Jam—showcasing the power of basketball to connect youth, build confidence, and create pathways to opportunity in Southeast Colorado Springs. | |
Girls 3V3 Basketball Tournament
Carmel Community School
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Second year of an exciting Girls 3v3 Tournament, welcoming 40 participants across 10 teams (five Hoopsters and five MiddleStars) for a weekend filled with competition, growth, and community. Athletes brought energy and heart to the court as they showcased teamwork, skill, and sportsmanship.
The tournament crowned champions in both divisions and was proudly Rocky Mountain State Games endorsed, with support from community partners and vendors who helped make the experience memorable. From inspiring guest speakers to meaningful prizes for standout performances, the event celebrated the strength and potential of our young female athletes.
Hillside Connection is proud to continue creating spaces where girls can compete, build confidence, and grow as leaders on and off the court.
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Business Immersion Series
Downtown Colorado Springs x COS Black Chamber
| | | | This Spring and Summer delivered an impactful Business Immersion Series with 10 of our business-minded young entrepreneurs, designed to empower youth with real-world entrepreneurial and career-ready skills. Through hands-on workshops, expert mentorship, and project-based learning, participants gained foundational business literacy and confidence to lead in any field. | |
4th Annual GameLikeHer Basketball Clinic
Carmel Community School
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Empowering the next generation of young women! Hillside Connection and NBA Skills Trainer (Kieon) hosted the 4th Annual GameLikeHer basketball clinic for 60+ elementary and middle school girls in the heart of Southeast!
The clinic consisted of basketball drills, vision board stations, brunch, and an impressive group of women empowerment panelists (see below).
“This is such an exceptional program for girl's empowerment! The panel for the GameLikeHer camp was phenomenal! Hearing stories of success from women of color was powerful! (My Daughter) really loved their stories and said it made her feel like she could do anything she puts her mind to.” Hillside Connection Parent
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Biddy Basketball Academy
Hillside Community Center
| | The Biddy Academy was all about learning, growing, and believing in what’s possible both on and off the court. Thanks to Biddy Academy, we had an incredible time helping young hoopers sharpen their skills, build confidence, and embrace the power of the game. Every kid also walked away with a copy of "What If" created by Hillside Alumni DeLovell Earls. The book that challenges us to dream big, push past fear, and ask what if I can? The journey doesn’t stop here keep dreaming, keep working, and keep believing. | | |
Heartbeat HoopRun:
Inaugural Year for High School Seniors
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This fall marked the inaugural year of Heartbeat HoopRun for high school seniors, creating a free, consistent space centered on competition, development, and fellowship. More than just open runs, Heartbeat HoopRun brought student-athletes together to build community on and off the court.
Over 10+ sessions from June through October, runs were hosted at Memorial Park, Palmer High School, and Sierra High School. Each session included competitive play and empowerment conversations that supported leadership and connection.
The season closed with a celebration featuring music, live games, prizes, and a free BBQ—ending a strong first year and setting the stage for continued growth.
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Summer Jam Finale and Giveback
August - September 2025
| | Our Summer Jam Community Day Block Party gave away over 200 HC branded backpacks stuffed with school supplies to get local students ready for the year ahead! | | Our team partnered with school districts to provide additional backpack and school supply support for young kids. | | |
Our Giveback was hosted at Solid Rock Food Center, where our efforts made a real impact, serving 519 individuals across 167 households.
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Looking Forward
January Activations
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