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History of East Hill Farm: The Early Years

What a journey the past 74 years have been!  From the early days of housing only 30 guests, to our current capacity of 140, we have been fortunate to meet and make many lifelong friends that call East Hill Farm their home away from home. You are truly our extended Farm family!

The Inn at East Hill Farm will be celebrating our 75th Anniversary during the weekend of February 4-6, 2022. As with all celebrations, it is more fun to have your friends and loved ones to celebrate with. Please mark your calendars and consider joining us for this momentous occasion!

We will be sharing photos, behind the scenes and fun stories in a series of monthly blog, Instagram, and Facebook posts leading up to the celebration. While the Inn’s history dates to 1772, we are focusing on what it has been since right after WWII, an agritourism destination. 

In our first post we begin with the earliest days of the Inn…

In 1765, Silas Fife, the first resident of East Hill Farm lived in a dugout cave, near the present-day skating rink, where nightly fires were kept burning to ward off mountain lions and wolves which roamed the area. Soon Silas married, built a log cabin, and cleared the land for farming to provide for a family of ten children.

In 1810, the farm was sold to Caleb Perry of Fitchburg, Ma. During this time, East Hill, Monadnock Number Five was incorporated as the town of Troy. The territory was formerly part of Marlborough, Fitzwilliam, Swanzey, and Richmond. On July 20, 1815, the first town meeting was held. Caleb Perry was elected town selectman. 

Able Baker, of Marlborough, married Cordelia Perry (Caleb’s daughter) in 1821. He bought the farm from his father-in-law and was active in town affairs. He taught school during the winter and farmed in the summer.

Baker sold the farm in 1828, to Amasa Aldrich of Richmond, NH. He was also busy with town affairs and served on the school committee.  

In 1867, Oliver and Ellen (Parker) Whitcomb bought the farm from Amasa Aldrich. They were very busy operating the farm. Oliver cut hay by hand for the first two years, farmed 35 acres, planted corn and potatoes, and raised milk cows. The Whitcombs raised five children, Frank Albert, Nettie, Emma, Jennie, and James (who was born in 1888).

The Whitcomb children in front of east hill farm house
Nettie, Emma, Jennie, and Ellen Whitcomb

Oliver kept cows for farmers from Massachusetts as well as his own. Farmers from nearby Wayland and Maynard, Massachusetts would drive (by foot and on horseback) their cattle (around 400 or so) to New Hampshire to graze the pastureland on Gap Mountain and Mount Monadnock for the summer. The farmers, for a mere seventy-five cents, would stay overnight at the inn, and enjoy two hearty meals before returning home. These were the inn’s first paying guests.

shepherd with flock of sheep at east hill farm

Other livestock that grazed the pastures were sheep. They were washed at what was properly called “The Sheep Hole”, located down past the waterfall on the way to Gap Mountain.

Ellen was, by all accounts, a first-rate cook. Her daughter Emma wrote home longingly for her mother’s blackberry pies, gingerbread, cream cakes, and the like. And Jennie learned to make biscuits and crabapple jelly with recipes from her mother. 

The early 1900s brought about a barn raising and new additions to the main inn. After Ellen passed away in 1920, Jennie started taking in “summer people”. The first cabin was built around the same time. By 1934, a large two-story addition was built at the back of the inn.

Oliver passed away in 1936 at age 90.  

east hill farm house 1836

Join us next month as we pick up the story when Parker Whitcomb (Oliver and Ellen’s grandson and son of Jim Whitcomb) returns from war with a plan for change.

Post submitted by Holly LeClair


  1. mary muir on February 20, 2021 at 5:43 pm

    wow thanks for sharing this I love reading it and making special connections to the Inns past. It is not surprising how close you all are to the energy, ethos and essence of what makes it such a special place looking forward to hearing the Rest of the Story

    • Jennifer on February 21, 2021 at 10:30 am

      Thanks for reading the blog and for your comments. We look forward to sharing more of the story. Stay tuned!

    • Sarah Bernardi on February 22, 2021 at 12:09 pm

      Thank you for sharing this! It was wonderful to read! Such a fascinating history! I’m looking forward to the next chapters!

      • Jennifer on February 22, 2021 at 1:50 pm

        We have lots of fun looking through old pictures and documents to gather and present the history to you. Looking forward to the next year of sharing!

  2. Daphne Negron on February 21, 2021 at 3:13 pm

    Wow! Interesting information. I can’t wait to hear the rest!

    • Jennifer on February 21, 2021 at 3:50 pm

      Thanks for the feedback! We look forward to sharing more with you in the coming months.

  3. Daniel Bisaccio on February 22, 2021 at 9:52 am

    Enjoyed reading the first installment of the history of EHF! Interesting genealogy and evolution of of a farm in the Monadnock region.

    • Jennifer on February 22, 2021 at 10:34 am

      Thank you! We are looking forward to continuing the story. Stay tuned.

  4. Patti Colombo on February 22, 2021 at 11:44 am

    Wonderful to read and learn about our favorite place and the state we call home. Also, to have photos was the icing on the cake! I look forward to reading more and to seeing more photos—thank you for sharing!

    • Jennifer on February 22, 2021 at 11:46 am

      We are glad you enjoyed a bit of EHF history. Stay tuned for more of the story!

  5. Ann Merritt-Mullins on February 22, 2021 at 12:39 pm

    Love seeing Mom’s photos and info about the homestead being shared!!
    Ann Merritt-Mullins

    • Jennifer on February 22, 2021 at 1:48 pm

      Thanks to you and your family for the contributions you have made over the years as we collect and share history of East Hill Farm.

  6. Anonymous on February 22, 2021 at 2:37 pm

    Absolutely wonderful!

    • Jennifer on February 22, 2021 at 2:41 pm

      Thank you!

  7. Jan Merritt on February 22, 2021 at 2:43 pm

    As a Whitcomb-daughter of Jim Whitcomb and granddaughter of Oliver and Ellen- I can only say Keep it up. !Wonderful to see all this story so others can enjoy too. East Hill Farm has happy memories for many besides family!

    • Jennifer on February 22, 2021 at 3:25 pm

      We always appreciate and welcome your stories. Please share what you would like as we travel through time.

  8. Judy Luopa on February 22, 2021 at 2:55 pm

    That was very interesting ! I grew up on the same Road back when Parker& Julie owned it. I love reading this history ! Please keep it coming . will look forward to the celebration !

    • Jennifer on February 22, 2021 at 3:24 pm

      Please add to the story when we get to the era of Parker & Julie. We would love to hear your stories.

  9. Carrie Mattson on February 22, 2021 at 4:43 pm

    Thank you for sharing very interesting. I have read the history but this is a great story that deserves reading many times! Troy is blessed to have East Hill Farm❤️ Carrie

    • Jennifer on February 22, 2021 at 5:03 pm

      Thank you so much! We can’t wait to keep sharing the story.

  10. Brian Bernhardt on March 25, 2021 at 11:00 am

    I am Brian Bernhardt and my parents Ralph and Eleanor stayed at the Inn for most of 60’s the first two weeks of July and over New Years. They were good friends with Parker and Julie. They also knew Anna Whitcomb. The other families that stayed there at the same time were the Kings and Guaraldi.s to name a few. This went on for many years. When I was younger going to the Inn was the highlight of my year! At the time Dave was the handy man and Sally was a waitress. If you let Dave and Sally know I wrote this, I am sure they will remember me, my family, and the families that I mentioned. I do have movies that my father took of the Fourth of July parade, water skiing at Silver Lake, skiing from rope tow on the hill behind the Inn and the cocktail parties with manhattans. I know where these movies are and will try to have them transferred to a flash drive for you to look at. Tell Dave and Sally I say hi! I live in Milwaukee WI now.

    • Jennifer on March 25, 2021 at 11:25 am

      Hello Brian- Thanks so much for sharing you wonderful memories of East Hill Farm. I will pass on your message to Dave and Sally. It is so fun to think about how many of the traditions from the early days of East Hill Farm are still continuing today. We would love to see your movies if you are able to get them into digital format. Cheers! Jennifer (Dave & Sally’s daughter)

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