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 kids ages 6–15 through facilitated play.
Join Us at Pokéfest — Nov 15 →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.
Level Up Inc. is a Massachusetts 501(c)(3) nonprofit. Today we run a monthly Board Game Bonanza with the Sawyer Free Library, a free monthly Community Commander Night at the Gloucester Fraternity Club, and starting December 2026, the Level Up Game Club with the Cape Ann YMCA's after-school program at five elementary school sites.
This summer's two trial days at Lanesville Community Center confirmed what we hoped: real kids, real growth. One parent told us their son “definitely gained more confidence in D&D, and also brought back his interest in Pokémon cards.” Another said hers “met new friends and connected with friends from other schools.”
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 holds a Master's degree in Higher Education and has spent 20 years as a leadership and social justice educator at the college level — today as an adjunct professor teaching leadership at several Massachusetts colleges — building programs and large-scale events that help young people find their voice and their community. He brings that same academic grounding in leadership development 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
Pokéfest
A free, family-friendly Pokémon TCG community event — trading, battles, Learn to Play sessions, a Pikachu photo op, food, and local vendors. Sunday, November 15, 2026, 11am–4pm at the Gloucester Fraternity Club, 27 Webster St. Free entry, all ages welcome.
Follow for Updates →Level Up Game Club (After-school)
Facilitated tabletop gaming sessions in the Cape Ann YMCA's after-school program, focused on teamwork, sportsmanship, and leadership. Launching December 2026 at five elementary school sites across Gloucester and Rockport.
Click to Learn MoreBoard Game Bonanza at the Sawyer Free Library
A monthly drop-in game session for kids and their grown-ups at the Sawyer Free Library: board games, card games, and friendly facilitators. Free and open to Gloucester families.
See the Library CalendarCommunity Commander Night
A free monthly Magic: The Gathering Commander night at the Gloucester Fraternity Club, 27 Webster St. New and returning players welcome. Thanks to the GFC for donating the room.
See Upcoming Dates →School 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 15–18 (mature 15-year-olds welcome). 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 ApplyGet Involved
Donate
Every dollar buys games, trains facilitators, and keeps our community programs free. Level Up Inc. is a 501(c)(3) nonprofit, so your gift is tax-deductible to the extent allowed by law.
Give Now →Volunteer
Teach a game, run a table, or help at events. Adult volunteers complete a CORI/SORI background check and facilitator training. High schoolers can join our Junior Facilitator Program.
Email to VolunteerPartner or Sponsor
Local businesses can sponsor a program, a game library, or a community event, with recognition on our site and at events. Schools and youth organizations: let's talk about bringing Level Up to your kids.
Become a PartnerJoin Our Board
We're growing our Board of Directors. We're especially looking for people with finance or bookkeeping, education or school counseling, and fundraising experience, and for parents of kids in our programs.
Express InterestWith thanks to our partners and supporters: Cape Ann YMCA · Sawyer Free Library · Gloucester Fraternity Club · Cummings Foundation