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Fun things to do at New England Boarding Schools in the fall

Photo by Jason Lee '15

Photo by Jason Lee '15

Fall in New England is a favorite time of year for many. From foliage to fall food favorites, there’s a definite culture that can be found in this area, and at many of the boarding schools in New England.  We’ve picked our top 5 favorite fall activities that many New England boarding schools offer for both boarding students and day students as weekend activities.


Check your weekend activity calendar and be sure to sign up to go apple picking at a local orchard. Wandering the rows of apple trees picking the reddest and ripest apples is something every New Englander has done in their lifetime. Whether Gala, Red Delicious, McIntosh, Cortland or Honeycrisp, most of the orchards also offer fresh cider, cider donuts, apple pie, and maple candy, too. Ask a dorm parent to sponsor an apple pie bake-off or make your own candy apples or caramel apples. The Town of Cheshire itself has three apple farms for optimal picking.


IMG_5991Foliage Viewing

You might even find this activity right on your own campus. With most New England boarding schools situated on more than one hundred of acres of land, chances are there are myriad opportunities to watch the leaves change colors. A day trip to Vermont, known for it’s fabulous foliage, might be offered, too. And for those digital photography students out there, don’t forget your camera. Happy leaf peeping!



For many, this goes hand in hand with scoping out the foliage, but the cool, crisp weather is perfect for hiking around New England. Boarding schools often offer trips to local mountains and trails where you can take in gorgeous scenery, get some exercise, and have fun with friends. For example, Sleeping Giant Mountain in nearby Hamden overlooks Cheshire Academy and offers up amazing trails for every level of hiker.


Ask your student life office if they can book a biking day trip for students. From local rail trails to mountain biking in state parks, the fall is an ideal time to explore the area. Coastal areas even offer routes along the shoreline.

Corner of 45th and 65 S.Pumpkin Picking

With fall officially in full swing and Halloween right around the corner, pumpkin picking is a perfect activity. Wandering the pumpkin patches in search of the ideal pumpkin can be a wonderful weekend activity. And once you get home, show your creativity and carve a jack o'lantern. You might even be able to convince your dorm parents to help you roast some pumpkin seeds or make a pumpkin pie.


If these activities aren’t offered at your boarding school already, ask your student life office if it’s possible. Chances are, they’ll make it happen!

Stacy Jagodowski

Written by Stacy Jagodowski

Ms. Jago joined the Cheshire Academy community in August 2013 as the director of strategic marketing and communications. Prior to coming to Cheshire Academy, she spent six years working in communications offices at both colleges and private school, as well as five years in admission at both boarding schools and day schools.

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