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Things To Do in Boston This Weekend: June 20 – June 22

Boston’s summer scene is heating up with various food, music, and arts festivals taking place throughout the city. Indulge in slices at the Boston Pizza Festival, soak in creative energy…

Pizzeria glass window. Variety of italian pizzas in a shop display, street food. Kitchen workers arranging the pizzas.

Boston's summer scene is heating up with various food, music, and arts festivals taking place throughout the city. Indulge in slices at the Boston Pizza Festival, soak in creative energy at the Cambridge Arts River Festival, and celebrate LGBTQ+ voices at OUTLOUD Boston. The city's theaters also feature live music and comedy performances throughout the weekend.

Boston Pizza Festival

  • What: Boston Pizza Festival
  • When: Saturday, June 21, 2025, 11 a.m. to Sunday, June 22, 2025, 6 p.m.
  • Where: City Hall Plaza, 1 City Hall Plaza, Boston
  • Cost: Entry is $10 with two slices of pizza ($15 at the gate); add-ons include a three-slice pack for $11.99, a five-slice pack for $17.99, and a 10-slice pack for $31.99

The Boston Pizza Festival returns to City Hall Plaza, celebrating its sixth year as New England's largest consumer pizza event. Over 30 pizzerias — including local favorites and international guests — will serve slices from Marra Forni artisan ovens. Attendees can enjoy live music, cooking demonstrations, a kids' pizza-tossing station, and a beer and wine garden — all in a cashless, family-friendly setting.

Cambridge Arts River Festival

  • What: Cambridge Arts River Festival
  • When: Saturday, June 21, 2025, from 11 a.m. to 6 p.m.
  • Where: The banks of the Charles River along Memorial Drive, JFK Street, and Western Avenue in Cambridge
  • Cost: Free

The entirely free Cambridge Arts River Festival, beloved since the 1970s, came back to life in 2024. This year, the River Festival transforms the streets of Cambridge into an exciting hub of entertainment, featuring six stages of live music, dance, theater, and poetry. Highlights include a whimsical mermaid promenade, hands-on art-making activities, strolling performers, food trucks serving cuisine from around the world, and an art and crafts market featuring a diverse mix of talented artists. The River Festival brings together culture, creativity, and community, making it a staple summer event.

OUTLOUD Music Festival Boston

  • What: OUTLOUD Music Festival Boston
  • When: Saturday, June 21, 2025; gates open at 2 p.m.
  • Where: The Stage at Suffolk Downs, 525 William F. McClellan Highway, Boston
  • Cost: General Admission Lawn $69.42, General Admission Pit $99.50, and VIP $172.18

OUTLOUD Boston is a three-day LGBTQ+ music festival and celebration of queer artistry, community, and expression. Featuring headliners Kim Petras, a global pop sensation, and Trixie Mattel, a world-renowned drag performer, and numerous other artists, including Flo Milli, Rebecca Black, G Flip, and Frankie Grande, the festival will have you rocking all weekend long. Celebrate live music and the arts with immersive art installations, food, drink, and the awesome, vibrant OUTLOUD Boston community.

Other Events

Boston's theater district is packed with standout performances for all music lovers and comedy fans. From heartfelt tributes and Latin folk-pop to sharp-witted stand-up, the lineup promises memorable nights on stage.