About the Inn

Meet Your Innkeeper

Hello!  I’m Amy.   Welcome to Brewster By The Sea Inn!

I purchased Brewster By The Sea Inn in 2016, after practicing law for a bit, and retiring from a 25-year career doing acquisition work for non-profit land conservation organizations, primarily in Oregon and California.  Growing up in the suburbs of New York, I came to the Cape each summer as a youngster, fell in love with it, and knew this was where I wanted to live someday.  So count me in as a another wash-a-shore, who loves everything about this magical spit of land, and enjoys sharing it with visitors from all over the world!

What to Expect at Brewster By The Sea Inn.

After the Covid pandemic, I reduced the number of rooms at the Inn from nine to four.   With just four rooms, and fewer guests coming and going, the Inn has a boutique feel to it — calm and quiet.

We don’t have too many formalities here.  My goal is to create a place where you can relax and unwind.  I am here to provide information and suggestions about what to see and do on the Cape, and of course, to make and serve you a delicious breakfast each morning.   I am happy to accommodate any type of dietary restrictions.

I do like to keep an eye out for you as you arrive, to welcome you, show you around, and to see if you need any assistance with your bags as you head toward your room.   I will text the room’s lock code to you on the morning of your arrival, and you are welcome to head straight to your room when you arrive – no need to go to the Main House to “check in.”

All of the rooms are located in the guest house, which is named, The Orchard House.  The Main House has a spacious Common Room, with a small library of books about the Cape ready for you to peruse.  This is where breakfast is served during the winter months, or rainy days in the summertime.  The salt-water pool with its surrounding mahogany deck, and screened-in gazebo are favorite lounging spots all summer long.  Our mini-Provence lavender garden in the yard behind the Orchard House is lovely to sit beside for the three Rs – rejuvenating, reading and relaxing.

Breakfast is served each morning between the hours of 8:00 and 9:30. As soon as it is warm enough, breakfast is served outdoors on the deck.  Once you have selected a table, I will first bring you coffee or tea, and describe the breakfast of the day.  I typically alternate between a sweet and savory breakfast each morning.  I’ll start you off with fresh fruit and a baked item that you may enjoy while I prepare your breakfast in the kitchen.

Brewster is the perfect central location from which to explore the Cape, and after breakfast, you’ll most likely be off on your daily adventure, be it biking on the rail trail, beaching it at one of the Cape’s fabulous beaches, shopping, antiquing, whale watching, hiking, fishing, golfing, or visiting museums and galleries.  And when you tire, come back to the Inn for a rejuvenating swim before you head back out for dinner.

I look forward to hosting you, and I thank you for making Brewster By The Sea Inn a part of your Cape Cod experience!

Amy Chesnut, owner of Brewster by the Sea.
Amy Chesnut, Owner and Innkeeper

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HISTORY

As you drive around Brewster you will notice that many of the streets bear the names of the families who settled in this area. Brewster By The Sea Inn’s roots are deeply connected to several of those families – The Dillinghams, The Fosters, and the Newcombs.

The Dillinghams

Just up the road, west of the Inn, is the oldest house in Brewster – the Dillingham House, which dates back to the late 1600’s.

John Dillingham was born in Sandwich, England in 1630. He and John Wing purchased much of the land in Brewster from three American Indians in 1676. John Dillingham built his house, lived a quiet and peaceful life here, and died in 1715. His only son, John, inherited his house.

John Dillingham, Jr., had a daughter Polly, who fell in love with Nathan Foster. The two were married in 1803, and lived in the Dillingham house with Polly’s parents.

John Dillingham passed away in xxxx, and, in 1846 when Polly’s mother died, the home passed to Polly’s older brother. Nathan and Polly left the home, and, while still on the Dillingham property, built a farmhouse which was to become Brewster By the Sea Inn. The front door of the farmhouse was located where the westside entrance is today. The house had a kitchen (the Emerson Room), a living room (the westerly portion of the main gathering room), and two bedrooms upstairs (the Loft Suite). The fireplaces in these rooms are the original fireplaces Nathan Foster built in 1846.

The Fosters

By the time Nathan and Polly Foster built their new home, they had already raised their children in the Dillingham house. Nathan was 68 years old, their children were 42, 39 and 35.

Nathan and Polly grew old together in their new house, and were taken care of by their unmarried niece, who also had the name Polly. When Nathan passed away, he gave his estate to his wife, and made provisions that his niece, Polly, could stay and live in the house for so long as she was single. In 1863, Polly Foster passed away, and the house was inherited by their only son, Nathan Foster Jr., who by that time had been a successful merchant in the town of Harwich for over 40 years.

Nathan Foster, Jr. lived in the home until his death in 1891. Not much more is known about him, other than he continued to farm the land.

The Newcombs

There must have been familial ties between the Fosters and the Newcombs, because the house passed through the Nathan Foster, Jr. estate to the Newcomb family – most likely Nathan Henry Newcomb. From there the home passed to Nathan Henry’s and his wife Evelyn’s two sons – Valentine Bernard Newcomb and Ahira Percy “AP” Newcomb. It is not clear when the house was enlarged from the original footprint, but it must have occurred by the time the Newcomb boys inherited it – because the two brothers and their wives lived in the house. It had two separate kitchens, living areas and bedrooms, because it is well- documented that the two brothers did not speak to each other for over 20 years!

Valentine Newcomb was a farmer, and was the one who maintained the land as an asparagus farm, with acres of orchards, as well as cattle, sheep and chickens. The kitchen in his part of the house is where the Garden Room is now.

AP Newcomb was Brewster’s town clerk and treasurer and his office was on the east side of the main house – where the kitchen is currently located. He held this office for many decades and it is said he was highly respected, (although the posting of properties in arrears on taxes was not always well advertised.)

What is now the Orchard House was the barn for the farm. In 1940 the garage was likely added to the property, for an automobile.

A Bed and Breakfast

In 1966, AP Newcomb died, and two gentlemen purchased the house. They restored the Old Farmhouse, by removing two upstairs and two downstairs bedrooms in what is now the gathering room and dining room, added the front breezeway and the deck and pool. They opened the house as a bed and breakfast and it became famous for hosting famous actors and actresses from the Playhouse Theatre. The parties and goings on were legendary!

In 1998, the old barn was renovated into what is now the Orchard House.

Between 1966 and 2004, ownership passed on to five other owners, all of whom continued to run it as a Bed and Breakfast. It kept the name of The Old Farmhouse, until one owner renamed it “The Pineapple Place” in tribute to the warmth and hospitality to be found here.

In 2004, Donna and Byron Cain purchased The Old Farmhouse, and renamed it, Brewster By The Sea Inn. They created a warm, inviting place for Cape-loving guests to stay.

Today:

In 2016, I bought the Inn from Donna and Byron Cain. I am particularly enamored with its history, and wonder about the genealogical connections. My roots go back to the Turner family, who were part of the Men of Kent who settled in Scituate as part of the original colonies. It is documented that the Foster family and the Turner family travelled at the same time from England to the colonies. Could they have known each other? It is something I often think about when I light a fire in the original fireplace. That and of all of those who have gone before me who have used that fireplace – to cook, to warm the house, to read by, to celebrate holidays. I love that the home and its history is enjoyed by hundreds of guests each year – every one of them (you) bringing your own remarkable stories and leaving a part of yourselves to become a thread in the fabric of this house’s story.

Thank you for staying with us!

The Best of Cape Cod