Weekends at Hillside are a time for exploration, enrichment, and fun. Seven day boarders (plus other students who elect to join in on activities) enjoy the many advantages of our proximity to Boston and a variety of historical, cultural, and sporting amenities. Each weekend, students choose from on- and off-campus options, from a trip to the beach to time in the Innovation Center. Adequate time to relax with friends and catch up on rest is also built into weekend schedules.

Hillside boarders are encouraged to join day or five day students who live locally for an occasional weekend homestay. Boston-based boys regularly invite their friends from across the country and around the world to become a part of their family for a weekend -- our international students particularly appreciate the chance to see and experience American culture firsthand.

Weekend activities and trip destinations include:

  • Ice Skating
  • Festival of Trees
  • Skiing/Snowboarding
  • Canoeing
  • Innovation Center
  • Escape Room
  • Tours of Boston-area colleges and universities
  • Old Sturbridge Village
  • Natural Museum of History
  • Boston Art Museums
  • Sports Simulators
  • Frisbee on the lawn
  • Go-Karts
  • Walden Pond
  • Boston Museum of Science
  • Local college athletic contests
  • Red Sox games
  • Boston Aquarium
  • Religious services
  • Freedom Trail of Boston
  • Events at the TD Garden (Bruins, Celtics)
  • Basketball Hall of Fame
  • Cape Cod National Seashore

A time for exploration, enrichment, and fun!

Hillside's weekend schedules take full advantage of the many enjoyable enrichment activities afforded by the School's proximity to historical, cultural and sporting amenities. Students are also ensured adequate time to relax with their friends and enjoy on-campus activities at the farm, pool, library, gym, etc.