Gallery
Yale Shop
The Yale Shop on Bailey Island. This shop is also fondly remembered as Olive Mathieson’s store. She had a tea room and a soda fountain in the north end and a grocery story at the south end. The road behind is Rt. 24, the steamboat wharf is in front.
Tuna Tournament
A great day’s catch for the contestants in a week long tournament, held at Mackerel Cove, Bailey Island. circa 1940’s
Prince’s Point
Prince’s Point at the southern end of Orr’s Island, ME
The Pearl of Orr’s Island
In 1862, the novel, The Pearl of Orr’s Island, by Harriet Beecher Stowe, was published. In this photo, the Pearl House is in the bottom left corner with the southern end of Orr’s Island at the top.
Orr’s/Great Island Bridge
The bridge connecting Orr’s and Great Island was privately built between 1833 and 18 45. In 1852, the bridge was given to the town of Harpswell. The bridge was destroyed in 1857 and rebuilt by the town.
Orr’s Island
Orr’s Island, looking north with West Harpswell on the left. The road is Rt. 24
Mackerel Cove
This view is taken from Tip Top at the Southern end of Bailey Island, looking out the mouth of Mackerel Cove and across to Abner’s Point.
Land’s End
Land’s End Gift Shop on Bailey Island in 1945 at the end of World War II
Jennie Prince’s Ice Cream Parlor
Jennie Prince’s Ice Cream Parlor, located at the bottom right of Steamboat Road, Orr’s Island, Maine. circa 1915.
Ocean View Hotel
The Ocean View Hotel looked out of Mackerel Cove and to Abner’s Point. The road is Rt. 24. The Ocean View Hotel is no longer standing. Early 1900’s.
Antoine Fide’s Shooting Gallery
Antoine Fide’s Shooting Gallery located where the present Day Orr’s Island Post Office now stands.
Cribstone Bridge
The Cribstone Bridge, which spans Will’s Gut between Orr’s and Bailey Island, was open to traffic in September 1928. The 12 foot slabs pictured here are from Pownal and Yarmouth, Me. Gravity is the mortar.
Pebbly Beach, Bailey Island
Pebbly Beach, Bailey Island
Steamboat at Orr’s Island
Steamboat at Orr’s Island
Steamboat
Steamboat
Steamboat
Steamboat
Schoolhouse
Schoolhouse
Red and White
Red and White
Potts Point from the air
Potts Point from the air
!["The only one that anyone can identify is Oscar [Stuart]. The location is in front of Brehault's Haberdashery next toe Doctor Elliot's residence on the corner of Maine Street and Pleasant Street, the roof showing over the top of the stage is the Knights Pythias Building, present location of Loring, Short and Harmon*, formerly Chandler's and there was another owner before that." From letter from Virginia G Stuart to Mrs. F. W. Browne, (no date) *In 2011 it was Wylers.](https://harpswellhistorical.org/wp-content/uploads/2026/03/cundysharborstage2.jpg)
Cundy’s Harbor Stage
“The only one that anyone can identify is Oscar [Stuart]. The location is in front of Brehault’s Haberdashery next toe Doctor Elliot’s residence on the corner of Maine Street and Pleasant Street, the roof showing over the top of the stage is the Knights Pythias Building, present location of Loring, Short and Harmon*, formerly Chandler’s and there was another owner before that.” From letter from Virginia G Stuart to Mrs. F. W. Browne, (no date) *In 2011 it was Wylers.
Cundy’s Harbor Stage
“Oscar W. Stuart standing by his Cundy’s Harbor Stage is at his home in Cundy’s Harbor. The date is 1920. Oscar ran a regular daily schedule from Cundy’s Harbor to Brunswick, stopping at the train station, postoffice and hotelsd. He ran his route approximately 12 years.” From letter from Virginia G Stuart to Mrs. F. W. Browne, (no date)
Boat Landing, South Harpswell
Boat Landing, South Harpswell
Orr’s & Bailey Island from Harpswell Neck
Orr’s & Bailey Island from Harpswell Neck
General Store, Pott’s Point
General Store, Pott’s Point
General Store, Pott’s Point
General Store, Pott’s Point
map-of-Harpswell-1871
Orr’s Island from Bailey
Orr’s Island from Bailey
Southern Orr’s Island from the Air
Southern Orr’s Island from the Air
Steamer Landing, Orr’s Island
Steamer Landing, Orr’s Island
Orr’s Island Bridge
Orr’s Island Bridge
On the Shore of Orr’s Island
On the Shore of Orr’s Island
Beal’s Cove
Beal’s Cove
Orr’s Island Bridge Channel
Orr’s Island Bridge Channel
Town Hall
Town Hall
Bailey Store and Kellogg Church
Bailey Store and Kellogg Church
Steamboat Landing
Steamboat Landing
South Harpswell, ME Steamboat Landing
South Harpswell, ME Steamboat Landing
Schooner
Schooner
Sawyer’s Cove
Sawyer’s Cove
Orr’s Island from Bailey Island
Orr’s Island from Bailey Island
Orr’s Island Bridge
Orr’s Island Bridge
Orr’s Island Bridge
Orr’s Island Bridge
Nubble
Nubble
Moonlight, Bailey Island
Moonlight, Bailey Island
Merriman’s Store, North Harpswell
Merriman’s Store, North Harpswell
Mackerel Cove, Bailey Island
Mackerel Cove, Bailey Island
Mackerel Cove, Bailey Island
Mackerel Cove, Bailey Island
Dark Way, West Harpswell
Dark Way, West Harpswell
Mark Island Monument
Mark Island Monument
Kellogg Church, Harpswell Center
Kellogg Church, Harpswell Center
Kellogg Church, Harpswell Center
Kellogg Church, Harpswell Center
Meeting House, Harpswell Center
Harpswell Center, ME Old “Meeting House” built 1758-9. Used when saddle horses were tied outside and muskets stacked within. Attic was the arsenal for powder, flint and ball. Now is the Town House.
Old Town House, Kellogg Church and Store, Harpswell Center
Old Town House, Kellogg Church and Store, Harpswell Center
Old Town House, Kellogg Church and Store, Harpswell Center
Harpswell Center, Maine, The post office, town house and village church where Elijah Kellogg preached for many years.
Casco Bay, Harpswell Sound from Gurnet House
Casco Bay, Harpswell Sound from Gurnet House
Giant Stairs, Bailey Island, ME
Giant Stairs, Bailey Island, ME
Pearl of Orr’s Island
Pearl of Orr’s Island
backpathBack Path, Harpswell Center
Back Path, Harpswell Center
View from Auburn Colony, Harpswell
View from Auburn Colony, Harpswell
Driftwood and Edgecliff Hotels, Bailey Island
Driftwood and Edgecliff Hotels, Bailey Island
Sea Gables, South Harpswell, ME
The Sea Gables located at South Harpswell, Maine, is on a narrow neck of land extending about seven miles into Casco Bay; one of the most beautiful and attractive Summer Resorts along the Maine Coast, always ready to offer homelike hospitality and simplicity of summer life with the comfort and quietness which has made this place so popular in the past, with those seeking health, rest and recreation. Close by the water’s edge, it combines both country and seashore, overlooking Harpswell Harbor, Casco Bay and the ocean. From the many porches and sun room you have an excellent view of the many islands, woods and beautiful sunsets.
Sea Gables, South Harpswell, ME
The Sea Gables located at South Harpswell, Maine, is on a narrow neck of land extending about seven miles into Casco Bay; one of the most beautiful and attractive Summer Resorts along the Maine Coast, always ready to offer homelike hospitality and simplicity of summer life with the comfort and quietness which has made this place so popular in the past, with those seeking health, rest and recreation. Close by the water’s edge, it combines both country and seashore, overlooking Harpswell Harbor, Casco Bay and the ocean. From the many porches and sun room you have an excellent view of the many islands, woods and beautiful sunsets.
Sea Gables, South Harpswell, ME
The Sea Gables located at South Harpswell, Maine, is on a narrow neck of land extending about seven miles into Casco Bay; one of the most beautiful and attractive Summer Resorts along the Maine Coast, always ready to offer homelike hospitality and simplicity of summer life with the comfort and quietness which has made this place so popular in the past, with those seeking health, rest and recreation. Close by the water’s edge, it combines both country and seashore, overlooking Harpswell Harbor, Casco Bay and the ocean. From the many porches and sun room you have an excellent view of the many islands, woods and beautiful sunsets.
Sea Gables, South Harpswell, ME
The Sea Gables located at South Harpswell, Maine, is on a narrow neck of land extending about seven miles into Casco Bay; one of the most beautiful and attractive Summer Resorts along the Maine Coast, always ready to offer homelike hospitality and simplicity of summer life with the comfort and quietness which has made this place so popular in the past, with those seeking health, rest and recreation. Close by the water’s edge, it combines both country and seashore, overlooking Harpswell Harbor, Casco Bay and the ocean. From the many porches and sun room you have an excellent view of the many islands, woods and beautiful sunsets.
Otterbrook Farm, North Harpswell, ME
Otterbrook Farm operated by the Frank C. Dunning family 1901-1920 During a time of expansion they raised the entire first floor and built a new first floor under it as in the following photo. The capacity was 85 guests and they served 3 meals per day.
Otterbrook Farm, North Harpswell, ME
Otterbrook Farm operated by the Frank C. Dunning family 1901-1920 During a time of expansion they raised the entire first floor and built a new first floor under it as in the following photo. The capacity was 85 guests and they served 3 meals per day.
Old Fort Homestead, South Harpswell
Old Fort Homestead was owned by the Stover Family. This was originally an Indian fort. The house was passed down through generations of Stovers always with lots of children and each time excess guests showed up they would add another room eventually totaling 18 rambling from the main farm house plus the annex and at one point provided tenting platforms for the outdoors type. They were noted for various types exciting entertainment all summer long. Even when it was raining or foggy, they all had a good time. The Stovers set up for formal rentals in 1906. They advertised summer rentals in 1909 , the original farm house burned in1921 and the original old fort burned in 1926.
Old Fort Homestead, South Harpswell
Old Fort Homestead was owned by the Stover Family. This was originally an Indian fort. The house was passed down through generations of Stovers always with lots of children and each time excess guests showed up they would add another room eventually totaling 18 rambling from the main farm house plus the annex and at one point provided tenting platforms for the outdoors type. They were noted for various types exciting entertainment all summer long. Even when it was raining or foggy, they all had a good time. The Stovers set up for formal rentals in 1906. They advertised summer rentals in 1909 , the original farm house burned in1921 and the original old fort burned in 1926.
Old Fort Homestead, South Harpswell
Old Fort Homestead was owned by the Stover Family. This was originally an Indian fort. The house was passed down through generations of Stovers always with lots of children and each time excess guests showed up they would add another room eventually totaling 18 rambling from the main farm house plus the annex and at one point provided tenting platforms for the outdoors type. They were noted for various types exciting entertainment all summer long. Even when it was raining or foggy, they all had a good time. The Stovers set up for formal rentals in 1906. They advertised summer rentals in 1909 , the original farm house burned in1921 and the original old fort burned in 1926.
Oceanview Hotel, South Harpswell, ME
This was the biggest of the Hotels,built in 1884 first called Lawson’s Hotel . In 1901 it was bought by George Cambell who also owned the Merriconeag Hotel at the point 1901-1905. During it’s declining years one attempt at survival was to build a big swimming pool to attract guests. The foundation of this pool is still visible in the back yard of Mr. & Mrs. Ed Burkes’ house. The hotel burned in 1927 a mysterious 3 A.M. firm and story has it that the flames were so high the glow could be seen all the way to Brunswick. It burned so fast that the fire dept. could not save a thing and it was so hot that the cast iron tubs from the bathrooms three floors high actually stacked inside each other when the wooden floors gave way. Other owners were A.S. Young 1905-1911, Harry Lightfoot 1914, and Mrs. Lena Perry 1926 when it burned.
Oceanview Hotel, South Harpswell, ME
This was the biggest of the Hotels,built in 1884 first called Lawson’s Hotel . In 1901 it was bought by George Cambell who also owned the Merriconeag Hotel at the point 1901-1905. During it’s declining years one attempt at survival was to build a big swimming pool to attract guests. The foundation of this pool is still visible in the back yard of Mr. & Mrs. Ed Burkes’ house. The hotel burned in 1927 a mysterious 3 A.M. firm and story has it that the flames were so high the glow could be seen all the way to Brunswick. It burned so fast that the fire dept. could not save a thing and it was so hot that the cast iron tubs from the bathrooms three floors high actually stacked inside each other when the wooden floors gave way. Other owners were A.S. Young 1905-1911, Harry Lightfoot 1914, and Mrs. Lena Perry 1926 when it burned.
Oakledge, East Harpswell
Oakledge, East Harpswell
Oakledge, East Harpswell
Oakledge, East Harpswell
Oakledge, East Harpswell
Oakledge, East Harpswell
Nanatuck, West Harpswell
Nanatuck, West Harpswell
Merriconeag House, Potts Point, Harpswell Neck
Merriconeag House, Potts Point, Harpswell Neck
Merriconeag House, Potts Point, Harpswell Neck
Merriconeag House, Potts Point, Harpswell Neck
Merriconeag House, Potts Point, Harpswell Neck
Merriconeag House, Potts Point, Harpswell Neck
Merriconeag House, Potts Point, Harpswell Neck
Merriconeag House, Potts Point, Harpswell Neck
Merriconeag House, Potts Point, Harpswell Neck
Merriconeag House, Potts Point, Harpswell Neck
Lookout Point House
Summer inn was originally the old cookhouse of famed Lookout shipyard, which made sturdy vessels that sailed the Seven Seas.
Lookout Point House
Summer inn was originally the old cookhouse of famed Lookout shipyard, which made sturdy vessels that sailed the Seven Seas.
Lookout Point House
Summer inn was originally the old cookhouse of famed Lookout shipyard, which made sturdy vessels that sailed the Seven Seas.
Hildreth House
Hildreth House Opened in 1907 by Charles Hildreth and operated by various members of the Hildreth family It is on what is now called Hildreth Road. They featured shore dinners, out door and salt water activities with a 240 foot dock. Later owned by Dr. Otis Downs. The farm house still exists as is the residence of the Howlands.
Hildreth House
Hildreth House Opened in 1907 by Charles Hildreth and operated by various members of the Hildreth family It is on what is now called Hildreth Road. They featured shore dinners, out door and salt water activities with a 240 foot dock. Later owned by Dr. Otis Downs. The farm house still exists as is the residence of the Howlands.
Guernsey Villa, West Harpswell, ME
Guernsey Villa, West Harpswell, ME. Extensive shady lawns, commodius verandas fanned by sea breezes
Guernsey Villa, West Harpswell, ME
Guernsey Villa, West Harpswell, ME. Extensive shady lawns, commodius verandas fanned by sea breezes
Guernsey Villa, West Harpswell, ME
Guernsey Villa, West Harpswell, ME. Extensive shady lawns, commodius verandas fanned by sea breezes
Videos
Voices of Harpswell
These oral history videos were recorded in 2020 as part of the commemoration of the 200th anniversary of Maine statehood. They represent unique insights into the history of Harpswell by a broad cross-section of Harpswell residents.
Glimpses of Harpswell
This video is a compilation of photos from the book "Glimpses of Harpswell," which was made to commemorate the 200th anniversary of Maine statehood in 2020.