Building leaders and community, one game at a time.
Level Up Gloucester uses tabletop gaming, including board games and role playing games (such as Dungeons & Dragons), to teach essential life skills to children ages 6-13 through facilitated play.
Register for August 21 or 28 →See a sample schedule →
Mission Driven Play
Level Up Gloucester is a mission-driven community program that positions gaming not just as entertainment, but as a primary vehicle for teaching essential social and cognitive skills to the next generation.
We believe in the power of facilitated play. Through structured tabletop gaming and community events, we provide an accessible, educational environment where children develop soft skills, leadership, communication, and conflict resolution in real-time.
Starting October 2026, we're partnering with the Cape Ann YMCA to bring this programming into their after-school program.
Built for Every Kind of Player
Some of the best facilitators, DMs, and players we know are neurodivergent — our programming is designed with that in mind, not as an afterthought.
Our approach is grounded by board member Shruti Tekwani, LMHC, a licensed mental health counselor who helps shape how we run sessions for kids who think, focus, and process differently. Facilitators are trained specifically in neurodivergent-inclusive facilitation — recognizing sensory needs, adjusting pacing, and knowing when a child needs space rather than redirection.
Every session comes equipped with fidgets, noise-reducing headphones, and a quiet space kids can step into if they need a break — no explanation required. We're also exploring dedicated sessions built around specific needs, including ADHD and Autism Spectrum Disorder. If that's something your family is looking for, email us and let us know — we're building this out based on real requests from families like yours.
Meet Our Founder
Higher education leadership educator, dad of two, and Dungeon Master of 25 years.
Steve Rossi has spent his career in higher education as a leadership and social justice educator, building programs and large-scale events that help young people find their voice and their community. He brings that same experience to Level Up Gloucester — decades of watching students grow into confident, engaged leaders, now aimed at kids just starting that journey.
A father of two and a Dungeon Master for 25 years, Steve has run more campaigns around the kitchen table than he can count, and he's seen firsthand what a well-run game can teach: how to listen, how to problem-solve under pressure, and how to root for the person next to you. Level Up Gloucester grew out of that belief — that play, done with intention, is one of the most powerful tools we have for building leaders and community.
Meet the full Board of Directors →
Fostering Group Development & Inclusion
Our Programs
Summer Pilot Program
Two trial Fridays — August 21 & 28, 9am–3pm at Lanesville Community Center. Board games, card games, and guided role-playing-game adventures (such as Dungeons & Dragons) for kids ages 6-13. $65/child full day ($40/child half-day) — siblings save $30/$15, sliding scale available — no child turned away.
Register Now → See a sample schedule →After-school Programming
Ongoing youth gaming sessions held after school hours that focus on developing life skills through structured tabletop play, in partnership with the Cape Ann YMCA.
Click to Learn MoreSchool Partnerships
Collaborative programs that bring tabletop gaming curriculum and life-skills development directly to local schools and organizations.
Private D&D & Family Game Nights
Facilitated, private tabletop game sessions tailored for families, birthday groups, or small circles of friends at their preferred location.
Email for More Information See sample schedules →Junior Facilitator Program
A volunteer leadership role for high schoolers ages 14–18. Junior Facilitators train alongside our adult facilitators, mentor younger kids, and earn verified community service hours — plus a reference letter after three or more sessions.
Email to Apply