Weekends are busy, vibrant times at Kents Hill School; no-one can claimed to be bored! On any given weekend, students will be found:
- Shopping in Freeport, Portland or Bangor...
- Playing pool in the Husky Den...
- Skiing at Sugarloaf or Sunday River...
- Taking in a movie in Augusta...
- Doing a midnight run to L.L. Bean or Denny's...
- Hiking, kayaking or fishing...
- Climbing with the Outing Club ...
- Working out, skating or shooting hoops in the Alfond Center...
- Hanging out at the Friday or Saturday night pizza, movie and skiing/riding party at the Ski Lodge...
Each weekend, trips are organized into town for shopping, movies and more. In addition, on-duty faculty organize ad hoc trips, depending on student desires and interest. Students and faculty have organized trips to Boston, dinner outings to various ethnic restaurants, trips to concerts in Portland, trips to performances and lectures at Colby, Bates or Bowdoin Colleges among others.