It is now run by Sally Middleton Littlefield wife of Jim Littlefield (now deceased) who took over the running of the business in 1965. This continues a proprietorship that was begun on July 4, 1889, with great hopes, by Jim's great-grandfather retired sea captain Emery H. Herrick and his wife Flavilla. It was Captain Herrick who hung a welcome sign over the door of their newly renovated homestead and proclaimed their new hotel venture open for business. That same sign greets Oakland House visitors to this very day.

Captain Herrick also gave his family name to the oceanfront landing on Eggemoggin Reach. This convenient ocean access was used for incoming rural mail delivery to Herrick's Landing and, in earlier days, for the lading of goods for export.

The land on which Oakland House was built had been acquired in 1767 through a grant to Jim's ancestors, John and Hannah Billings, from Britain's King George--a full nine years before the signing of the Declaration of Independence! The property has been handed down to direct heirs since then--from the Billings, through Flavilla Herrick and eventually, through Jim's father Elmir Littlefield (who also ran the hotel), to Jim Littlefield.

Back when the Billings owned the land, and Maine was struggling to gain a foothold in the young country's growing economy, the Billings used their naturally acquired "Yankee ingenuity" to find a niche in the commercial marketplace. In most areas of rural Maine--then and now--making a living can be a struggle. What they did was look to their own natural resources, which were granite and water, to make a living.

The elegantly beautiful granite that was abundant elsewhere in Maine also was present in great supply on the Billings' land. The quarry business had flourished in Maine for quite some time, and had supplied material for building projects worldwide. Granite from the Billings' land was used to build the towers and anchorages for the Brooklyn Bridge, and several Federal buildings, including the Bronx Court House in New York. During the Billings' ownership of the land an ice-cutting business was run on the property. Refrigeration was available, at that time, only by the direct and regular supply of ice to thousands of homes and businesses. The Billings' land had great access to spring-fed Lake Winnewaug (Walker Pond), a reservoir of clean, cold water which, during winter months, provided tons of crystal clear ice. The blocks were cut and stored in the "ice house" (now Oakland House's Hostel at Acorn), waiting to be shipped away on clipper ships to cities south of Portland, and to far away cities in California and China.

To this day, in places on the acreage that have since undergone subdivision, rusty narrow-gauge tracks can still be seen pointing in the direction of the water's edge. Jim's older brother Herrick remembers hopping in a small rail-cart, and zooming through the woods down towards the water...but there was no brake! He'll tell you the story; it's part of the charm of Oakland House.

Maine had, by that time, developed its primary industries of fishing and lumber harvesting but was, by a combination of geography and culture, out of the industrial mainstream. The Maine coast was pristine--an idyllic place of restful shorelines and hushed, wooded lands.

By the time Flavilla and the captain were married and had begun to raise a family, the need to earn a living and retain ownership of the land on the Eggemoggin Reach once again became an issue of paramount importance.

By the late 1800s, merchants, visitors, artists and writers brought images of Maine to the rest of the world. The great fashionable coastal summer "cottages" of the wealthy were providing an escape to the peace, quiet, and healthy environment offered there. City dwellers flocked to the countryside for a respite from city life.

Emery, intent on remaining on the land they loved, observed the successful development of coastal hotels and decided to turn the family homestead into a hotel. They sold his interests in ships, and sold off some of Flavilla's precious coastal land. The proceeds were used to expand the homestead into a hotel. They added the third story with its distinctive mansard-style roof. A sweeping verandah was added to provide visitors with a summer breeze no matter from which direction the wind was blowing. On that long-ago day, July 4th, in 1889, the Oakland House Hotel was opened for business.

From early summer into September, the captain would meet the steamboats and its passengers at the landing. He loaded the steamer trunks onto a wagon for the horses to pull up the hill to the hotel. The enthusiastic but exhausted guests would walk up the boardwalk from the landing, through the cooling oak grove, and arrive at the hotel just in time for lunch. Some of the cobbles from the Billings' granite works can still be seen on a few trails on the property. The frog pond is in a quarry depression.

In the early years it was not uncommon for guests--once they got the hang of it--to help milk the cows or work in the garden for a bit, such was their enjoyment of their country getaway. "Rusticators," they were called, eschewing the fancy city hotels in favor of a taste of country living.

The captain was able to continue his love for the sea by sharing with his guests the history of local islands and inlets, as he piloted them around the bay in a small passenger boat. It was no wonder that some families stayed at the Oakland House Hotel for a month or so at a stretch.

By the 1910-1920s the steamboats were giving way to other modes of transportation. Those folks daring enough to travel with "newfangled" horseless carriages started to arrive at the hotel from Boston, New Haven, and Philadelphia.

Back in those days guests made up their own fun, much as they do today. As yesterday's guests marveled at the rural environment, so do today's urban visitors. They have not only the fresh ocean breezes, delicious New England cuisine and crisp sheets, but also ample time away from telephones, faxes, televisions and newspapers. They have, also, an opportunity to bask in the tradition and history that made the Oakland House Cottages by the Side of the Sea and Hostel at Acorn what they are today.

Four Generations of Innkeeping--A Message from Oakland House's Present Innkeeper Sally Littlefield, Wife of Jim Littlefield (now deceased).

As a young woman, Josie (later called Gumma by her grand children) tended the lighthouse at Pumpkin Island, across the Eggemoggin Reach. Perhaps that's how she met the "other" sea captain in our family's lives, Jim's Grandfather Littlefield. However, his heart was at sea unlike Capt. Herrick's. Josie was soon running the hotel on her own, while raising Jim's father Elmir and his Uncle Frederic. Elmir obtained his higher education from Tufts University and brought his skills back home. He put the first plumbing into the historic Oakland House hotel in the 1920's and 30's and engineered the construction of the new cottages.

There also is a photograph of Jim's father, Elmir, and his mother, Katrina Littlefield, side by side. Elmir died when Jim was 14, so he started learning early about innkeeping, to help his mother to run the hotel. Jim loved it and couldn't imagine doing anything else.

Jim and I (Sally Middleton Littlefield) were married in a beautiful outdoor setting in the spring of 1994. Between us are four children: James, Bryan, Sally and Tim. One of my own ancestral cousins Arthur Middleton signed the Declaration of Independence (South Carolina)--the same year Jim's ancestor John Billings became a Selectman in the town of Brooksville, Maine.

I am grateful to Jim's brother Herrick Littlefield, our family historian, who compiled most of our family history. He has researched the contents of dusty old books, old photo albums, family letters, and visited libraries for bits of information. He set up countless interviews with relatives who knew of, or could remember, details of past events.

A guest who came to Oakland House first as a baby sent the fabulous old photo of the hotel building to us. The photo was in her parents photo album. We are grateful to her for making it available to share with you. We thank all of our guests, past and present, for allowing me to continue my family's tradition of welcoming you to Herrick's Landing and to the Oakland House Seaside Resort!

We posed for the photograph in June, 2007. From left to right in front is Jim's brother Herrick Littlefield, his sister Nancy Stine, Jim, and his brother John Littlefield. Behind us from left to right are: Herrick's daughter Lyn and her husband Claude Hoopes, Nancy's husband Fred Stine, Sally Middleton Littlefield, Jim's daughter Sally McGuigan, and John's wife Karen Littlefield.


OF JIM'S PASSING ON. Many of you have been vacationing at Oakland House for more years than I have been here. Jim Littlefield, 4th generation innkeeper, and I were married in 1994. He was the love of my life and I his. For 16 years we worked together in the operation of his family's coastal resort. At times Jim's daughter Sally and her husband Sean were with us. At times my sons Bryan and James worked here too. Bryan met his wife Justyna here. We had plenty of help.

In early 2007 Jim was diagnosed with multiple myeloma. Many, many of you were in touch with Jim through out his last 3 1/2 years and were well aware of his optimism and cheerful attitude toward life and living with his disease. Modern science and the best doctors were able to give Jim and me some wonderful extra time together. He enjoyed and revelled in each and every day. We had great moments.

While many people live many years with the disease, Jim's was more aggressive and it eventually took it's course. Jim lived to the fullest and died unexpectedly and peacefully on June 25, 2010 leaving a wonderful legacy and a strong group of guests and friends at his passing. His memorial service was held on September 4, 2010 with a large gathering of friends and family at Blue Hill First Congregational Church. His Obituary can be found on line. It is quite endearing and fun to read.

Of course every one asks me, "What are you going to do?" Now, with Jim as my mentor and spiritual guide, I'm continuing with the rental of cottages and private rooms in Acorn much as we did before. Time has been good to Oakland House and we've had good seasons as we've increased the number of cottages and private rooms available once again. With much of the same staff in place we will continue offering the same beautiful vacation opportunities Oakland House has since 1889. Our children, while not on site are helping in the background in many ways which continue to make this possible. We now are blessed with 7 grandchildren.

We look forward to hearing from you and seeing you in the coming season.