Chester Guild Cottage // 1902

One of the many stunning summer “cottages” built in the Cape Arundel summer colony of Kennebunkport, Maine, is this turn-of-the-century Shingle style dwelling built for Chester Guild of Boston. Chester Guild III was born into the wealthy Guild Family of Roxbury with his father being a successful leather dealer. Chester Guild spent summers with his family in Kennebunkport beginning in the 1890s, eventually had this cottage built in 1902. The Shingle style dwelling remained in the family for five generations and is very well-preserved, showcasing the hallmark elements of the ubiquitous coastal Maine architectural style.

The Billingsgate Cottage // 1892

In 1892, this large summer “cottage” was built in the Land’s End section on the coast of Rockport, Massachusetts. The large summer residence was built for the Thatcher sisters of Roxbury and was named “The Billingsgate” after their mother’s maiden name, Billings. Caroline Billings Thatcher would summer here with upwards of her four other sisters, Lillian, Margaret, Mary, and Elizabeth, to escape from the city. The large summer cottage features a rubblestone first floor with stone columns supporting the shingled floor above. A large gambrel roof and dormers punctuate the façade and showcase the simplicity and elegance of the Shingle style.

Windswept Cottage // 1909

The coastal towns of Gloucester, Manchester, and Beverly on the North Shore of Massachusetts often are known for their historic summer “cottages” but great examples can be found right here in Rockport! This is “Windswept”, the W. W. Blunt cottage, located in the Headlands section of town, just south of the harbor. Walton W. Blunt worked as the Treasurer and General Manager of the Boston Journal newspaper and resided in Boston, later purchasing multiple adjoining house lots in Rockport for a summer residence. The two-and-a-half story house was designed by a Rutherford Smith, who sought to utilize fieldstone found nearby for the foundation and chimneys and shingle siding above. Detailed descriptions of the new house were featured in a local newspaper in 1909 and mentioned tennis courts on the grounds, an apartment for servants, and a billiard room in the third floor. It is not clear when the house got its name, “Windswept”, but the name is just too fitting!

Streeter Cottage // 1882

In 1881, Gilbert Streeter and his wife Rebecca purchased a small house lot in the Salem Willows for a summer cottage for them to retreat across town to during the warmer months. Gilbert Streeter was an amateur historian, businessman, publisher of the Salem Observer and was able to afford a second residence in his hometown. The Streeter cottage was built by 1882 and stands out not only for its excellent state of preservation, but for its unique architecture. The cross-gabled form cottage is covered in board-and-batten siding with bargeboards lining the eaves.

Joseph P. Allen Cottage // 1877

One of the most picturesque and charming summer cottages (now year-round residences) in the Salem Willows neighborhood in Salem, Massachusetts is this Victorian on Bay View Avenue. The cottage was built around 1877 for Joseph Pray Allen (1822-1897) who was a police officer who likely climbed the ranks in the force to afford a second home in the city. The 1 1/2-story cottage has decorative bargeboards at the eaves and stick bracket at the gable. Perfection!

Patrick Dempsey Cottage // c.1875

This charming mini-mansard summer cottage is located in the coastal neighborhood of Salem Willows, in Salem, Massachusetts. The neighborhood developed in the 1870s-1900s as a summer colony for middle-income families who wanted a second home away from the hustle-and-bustle of urban living in favor of ocean breezes. The cottage likely dates to the mid-1870s as one of the earliest summer homes in the neighborhood, and historic maps show it was owned by a P. Dempsey. It appears this is Patrick Dempsey (1821-1902), an Irish immigrant who settled in Lowell, Massachusetts, making it big as a liquor dealer and saloon-keeper. The Second Empire style cottage has a partially enclosed porch, but retains much of its original character and is located right on the water with sweeping views of the Atlantic Ocean.

William Bates Summer Cottage // 1885

While Salem is best-known for its First Period and Federal style buildings, the Salem Willows neighborhood features some of the finest Victorian summer cottages in the Boston area. This cottage was built in 1885 by William Marston Bates (1820-1912), a Salem-based dentist, as his summer retreat when not in the office. The Stick style cottage has a steep gable roof with jerkinhead clip at the facade and a wrap-around porch with decorative jigsawn bracketed details. The house is a well-preserved example of the style, examples of which are becoming less-and-less frequent in recent years.

George N. Faught Chalet // c. 1890

The most unique house in Hull, Massachusetts is this stunning (and rare) example of a Swiss Chalet, located on Vautrinot Avenue in the fashionable Hull Hill neighborhood, which is dominated by late-19th century summer cottages. The earliest owner of the house was George N. Faught (1831-1915), an artist and tailor who moved to Boston from Maine. George went into the tailoring business in Boston and did well for himself, eventually building (and possibly designing) this summer home for himself in Hull. Mr. Faught died in 1915 in his bed in Boston, and this property was sold at auction in 1917. After some insensitive alterations in the 20th century, the property was sold in 2011. The later owners restored much of the house, while modernizing it to meet their needs. It is a showstopper!

The house is privately owned and not open for tours.

Miles Standish Cottage // c.1890

One of the larger summer cottages on Hull Hill is the Miles Standish Cottage, which dates to around 1890. The cottage was built after the nearby Hull Yacht Club was completed in 1882, which was apparently the second largest yacht club upon its completion. Owner L. Miles Standish was the first owner and the eclectic Craftsman/Shingle style cottage has been lovingly maintained by all subsequent owners. The house appears to now have the name “Last Best Place”, which is very suitable!

Galvin Cottage // c.1882

Hull Hill is a relatively unknown enclave of summer cottages that sit on a rise overlooking Boston Harbor in the coastal community of Hull. The development of Hull Hill began in the 1870’s but became most active in the 1880’s and 1890’s. The land here was previously maintained as pasture and gardens by Hull villagers, but the land here was eventually sold and developed when the Hingham Water Company came to Hull in 1882. That same year, the railroad arrived which provided easier access to the town. This cottage on Andrew Avenue is one of the earliest summer residences built here, and dates to the late 1870s or early 1880s. The cottage was owned by Owen Augustus Galvin, a Boston lawyer, and his wife, Jane Sullivan Galvin. The unique cottage features a hexagonal section with a roof extending down to meet the wrap-around porch. The cottage exemplifies late 19th century cottage/resort architecture.

Conant-Cushing House // c.1890

Atop the Great Hill on Point Allerton in Hull, Massachusetts, this large summer “cottage” stands out for its unique architecture and siting overlooking the bluffs and Atlantic Ocean. The Shingle style house was built around 1890 by Edward D. Conant, a real estate agent and developer of Newton as his family summer home. The architect is not clear, but the house exhibits a unique four-story crenellated tower, giving the appearance of a castle from a distance. The house was later owned by Cardinal Richard Cushing (1895-1970) as his own summer residence. Cardinal Cushing served as Archbishop of Boston from 1944 to 1970 and was made a cardinal in 1958. Cushing’s main role was as fundraiser and builder of new churches, schools, and institutions, and he helped then-presidential candidate John F. Kennedy deflect fears of papal interference in American government if a Catholic became president. Kennedy grew up spending summers at his grandfather’s home in Hull (featured previously). The Conant-Cushing House remains significant even with 20th century renovations.

Winfield S. Richards Cottage // c.1890

Summer cottages of the late 19th century are always a treat to come across! While most cottages I feature on here are more high-style and were built for the wealthy, Hull, Massachusetts, has some of the best middle-class summer cottages in New England! Steamships and rail service from Boston and other cities opened up Hull and Nantasket Beach to summer residents and day visitors alike, creating a massive increase in building in the latter decades of the 19th and early 20th centuries. This cottage was owned by Winfield S. Richards and his wife Myra of Newton, Massachusetts. The cottage blends Queen Anne and Craftsman styles with complex Queen Anne massing, turned posts, and recessed second story porch, and sloping roof extension to create the Craftsman-esque front porch. The cottage is one of the better-preserved in town and an excellent blending of architectural styles.

Bread Loaf Campus – Treman Cottage // c.1890

This is the last building to be featured on the Bread Loaf Campus! For more early history and context of the complex, check out the post on the Bread Loaf Inn. By 1900, owner Joseph Battell’s enterprise exceeded the capacity of the original inn, and cottages were added to accommodate more guests visiting his new permanent home in the mountains of Ripton, Vermont. Special friends who summered regularly at Bread Loaf purchased lots with water and sewage rights, and with Battell’s assistance, built their own family cottages to spend their summers. This is Treman Cottage, a shingled beauty which appears to have been built for a friend (though I am not sure who), and has since become the faculty cottage on the campus. As we wrap up this series, here is an interesting fact about the mountain campus: All buildings here that are painted the ochre color were built during Mr. Battell’s lifetime (by 1915), with later buildings painted white.

Bread Loaf Campus – Bridgman & Cornwall Cottages // 1881

Welcome back to the Bread Loaf Campus! For more early history and context of the complex, check out the post on the Bread Loaf Inn. By 1900, owner Joseph Battell’s enterprise exceeded the capacity of the original inn, and cottages were added to accommodate more guests visiting his new permanent home in the mountains of Ripton, Vermont. Special friends who summered regularly at Bread Loaf purchased lots with water and sewage rights, and with Battell’s assistance, built their own family cottages to spend their summers. The first two, Bridgman and Cornwall, were constructed across the street from the Inn around 1881 and are near-identical, modest vernacular cape houses with full-length front porches. The original owners were Charles William and Ellen Campbell Bridgman and Henry Bedinger Cornwall respectively. Both cottages have since been donated to Middlebury College and are important preserved pieces of its Bread Loaf campus.

Bread Loaf Campus – Maple Cottage // c.1900

Welcome back to the Bread Loaf Campus! For more early history and context of the complex, check out the post on the Bread Loaf Inn. By 1900, owner Joseph Battell’s enterprise exceeded the capacity of the original inn, and cottages were added to accommodate more guests visiting his new permanent home in the mountains of Ripton, Vermont. Located adjacent to the Mansard-roofed Birch Cottage, one of the most visually striking buildings in the campus is Maple Cottage, which reads more porch than cottage, but it’s 100% perfect. It was the last cottage built by Battell for his family and friends to stay at when visiting. They must have loved evenings on the three-floors of porches looking out over the Green Mountains.