Eastport Walking Trail

Settled after the American Revolution, Eastport’s 19th century prosperity grew from the sea trade, and was reflected in a bustling downtown and residential neighborhoods of relative affluence. A frontier town at the start, Eastport quickly grew into a trading city with 5000 residents. With a history of relatively rapid development, coupled with exposure to all that was trendy up and down the East coast, the town came to have a range of domestic and civic architecture within a small municipal footprint. Many examples of that early architecture still exist today, right within an easy strolling distance of the Eastport Farmers’ Market! The sites listed below are in the order in which you’ll find them on the walk, which will take about an hour at a leisurely pace.

Starting at the Eastport Farmers’ Market, proceed down Water Street towards town. Turn right at the Post Office (an eye-catching building made of granite from Blue Hill) and proceed up Washington Street, where the first stop on the tour will be on your right.  (For more options, and much more historical detail, pick up an Eastport Walk-About guide from the Border Historical Society.)



1. The McLarren House (11 Washington Street). With simple lines and a traditional double-chimney layout, this home is a good starting point for a tour of American architectural styles. Dated to around 1830, the home’s upright form speaks of solidity and lacks ostentation. Home builders at the time often relied on building techniques and design features they knew well, and thus a home like this might have details reflecting several styles, including Georgian colonial, Greek revival, and even country farmhouse elements. Whoever designed this home placed the bulk of the structure between the main entryway and the sea gales, a wise move in an area noted for its rugged climate.

The home belonged to Capt. John H. McLarren, a prominent ship owner and ship’s master, and later president of Eastport Savings Bank. Born in 1800, he emigrated to Eastport from Nova Scotia.  His first wife, Clarissa, died when she was just 27, and he 44. Capt. McLarren’s and his second wife, Matilda (who was 27 years his junior) ultimately had 6 children, no doubt filling the large home with activity. Capt. McLarren, like so many in the community, had diverse business interests. In addition to his work at the bank, he was one of the founding members of the Eastport Mutual Marine Insurance Society.




2. The Hayden House (17 Boynton Street). This large home was built in the post-Colonial Federal style in 1805, and is one of the earliest frame houses still standing in Eastport. The drawing above shows its earliest iteration, with six-over-six shuttered windows, a pedimented front door, and a simple roofline.  Later in the 19th century, the home was “modernized” with the addition of  a shingled, mansard roof and bay windows. (The mansard roof would have increased the living space upstairs, and the bay windows not only introduced more light into the home, but were a sign of affluence.) The result is a house reflecting a mix of architectural styles and periods.

The home’s first residents were the Hayden family. Deacon Aaron Hayden and his wife, Ruth, moved to Eastport shortly after their marriage in the fall of 1800. They eventually had 13 children. Deacon Hayden entered the merchant trade and was a proprietor of  Hayden, Jones, and Kilby. Aaron Hayden graduated from Harvard and eventually practiced law. Active in civil affairs, he was Eastport’s 19th representative to the Maine Legislature. Later Gen. S.D. Leavitt bought the home, and it was Gen. Leavitt who added the mansard roof and elegant bay windows.



Diagonally across the street from the Hayden house is the Weston House (26 Boynton Street). Harvard-educated attorney Jonathan Weston built his Federal style home in 1810. At that time, the house would have had excellent views of the harbor below. (Note the austere lines, simple roofline, and one-dimensional surfaces, in contrast to the more complicated facade of the Hayden House.) British officers were housed in the Weston House during the British occupation of Moose Island, from 1814-1818. Later, the famous ornithologist John James Audubon stayed at the home during visits to Eastport in 1832 and 1833. (Lately it has been operated as a bed and breakfast.)





3. The Central Congregational Church (Middle Street). Federal style – 1829. The church’s congregation organized in 1818 as the “First Evangelical Congregational Church and Society of Eastport.” A building committee was assembled, with builder Daniel Low in charge of a crew of ship’s carpenters. The Federal style church was dedicated in 1829, and is noted for its elegance, particularly considering that Eastport was yet a small, frontier community when the church was built! Forty years later, the church steeple blew off in a storm. When the tower was replaced, the clock was added as a modern touch. (Given the steeple’s high visibility over the town, the clock was surely much appreciated in the community.)




4. The Babb House (9 Key Street). This granite Gothic Revival home, built in 1869, is striking both in appearance and due to the history of the remarkable family who first called it home. With a steep pitched roof, rounded windows with rustic hood molding, and decoratively carved gable boards, the home stands out in contrast to the many stick built structures around it.

This solid structure was first home to the Babb family. In 1861, Sebago native Dr. Luther Babb moved to Eastport (after years out West, in Ohio and Indiana) to establish a medical practice. His wife, Dr. Eliza Millett Babb, obtained her medical degree from the Women’s Medical College in Philadelphia in 1871. Their daughter, Cora, also became a doctor, and their daughter Grace was the second woman to earn a degree in pharmacy from the Philadelphia College of Pharmacy. Most of the family moved to Florida in later years, but during the later 1800s, the Babbs were role models for the potential for women’s education.






5. The Norwood House (15 Key Street). This large, elegant home (built ca. 1824) features many characteristics of the Greek Revival style, including side and transom lights (windows) around the main door, louvered shutters, six-over-six, double-hung windows, a symmetrical design, and Ionic columns supporting the spacious, wrap-around porch. The basic structure of the house is similar to many in the area, with the porch and colonnade adding dramatic visual interest.

The home is notable for its role in post-Civil War history, when Irish-Americans rallied to support Ireland in trying to shake off British rule. The Irish rebels were called Fenians, and a number of them rallied in Eastport, planning to capture nearby Campobello Island from the British. Famed Union Major General George Meade quartered at the Norwood House (by then owned by the Whatley family) as part of the American effort to aid the British. Ultimately the rebellion was quelled, and Campobello Island remained firmly in British control. (Today visitors with proper I.D. can cross the bridge to Campobello and explore FDR’s family getaway, which is free and open to the public.)







6. The Hobbs House (11 Shackford Street). Colonial cottage with Federal addition. The first wing of this home (facing Middle Street) was built in 1823. It has a Colonial feel, with small windows, low ceilings, no attic, and a pediment over the door. The much larger front portion of the home is Federal in style, with gracious proportions, and a welcoming entry featuring a paneled door, fanlight, and sidelights.

Isaac Hobbs settled in Eastport in 1815, when he was just 22 years old. He married Emma Shaw (of Bucksport) four years later, and started building the family home just a few years later. Isaac was in business with his elder brother George, and such was the relative prosperity of the community that young men with growing families could build new homes.




7. Capt. William Shackford’s House (10 Shackford Street). Mid-19th century with Victorian embellishments. Like others in the area, William Shackford’s home was remodeled as styles changed. Parts of the structure may date to the early 1800s, and the front part of the house has the symmetry and simple lines common in area homes in the 1830s-40s. Much later (probably long after William Shackford’s death) the home was updated with Queen Ann period details popular in the late 1800s. A close look at the structure reveals later additions  such as the modest tower (which would have had a practical purpose, offering views of the harbor) and decorative porch.

The Shackford family originally settled on Shackford Head, where Revolutionary War veteran Capt. John Shackford  began a homestead in 1783. Captain Shackford brought his small family to  Eastport when it was still a frontier community made up of a handful of families, and “sheltering and sharing the gains of adventurers, smugglers, and gamblers” was commonplace. His son, William Shackford, was also a sea captain who frequently ventured far from Eastport. At age 29 he was captured by French pirates off the coast of Spain, was eventually ransomed, and made it back to Maine just before the British blockaded the American Atlantic coast. Captain Shackford eventually retired from sailing, became a merchant, married, and started a family. Three of his four sons went on to become sea captains as well.





8. The Huston House (6 Third Street). Second Empire – 1850s. The cosmopolitan nature of 19th century Eastport is revealed in the design of this home, with its Second Empire details inspired by mid-century Parisian architecture. The mansard roof with pedimented dormers is attractive, and meant that the third floor had plenty of headroom and light. The small stoop with its charming balcony adds to the European feel of the home. Bay windows at the front are typical Second Empire style, and were a perfect way for affluent families to take advantage of scenic views like those in Eastport.

The Houston clan moved into the home in the late 1850s, and surely appreciated the spacious design. Born in 1814, Caleb Huston was a successful Eastport ship builder who at one time operated 4 shipyards. As was typical of the era, over the decades, Caleb Houston’s household included children of varying ages (he ultimately married three times, having lost his first two wives to early death), parents, in-laws, and others.




9. The Peavey Memorial Library (26 Water Street) Romanesque Revival. In 1886 a devastating fire swept through downtown Eastport, leaving much of the business district a blank canvas for redevelopment. Whereas most private homes were designed by builders who merged local styles with current trends, Eastport businesses turned to architects to design their new structures. The result is evident in Eastport’s historic district, featuring many attractive brick buildings. One of these is the neo-Romanesque style library, built in 1893 by architects Rotch and Tilden. With its ponderous front arch, mullioned windows, and decorative details (including finials over the entry and a central cupola), the building conveys the solidity and connection to history suitable for a public institution.

The library is named in honor of Albert Peavey, an Eastport resident whose son, Frank Peavey, left money to Eastport to build the public library (with the caveat that town residents had to donate the first 5000 books). With fires striking blocks of wooden structures in other communities, such as Portland (1866) and Calais (1870), the post Civil War era was a time when architects found many commissions in Maine, and brick business districts became increasingly common.


10. Frontier National Bank (1882 Italianate). Now home to a private business, the elegant Italianate brick building (originally half the size it is today) was built in 1882, designed by architect Charles Kimball. Parts of the brick structure survived the The bank was organized in 1826, operating at the state level, and received a national charter in 1865. Currency printed at the bank is still available, and coveted by local collectors.



11. The Eastport Savings Bank Building (1887) Standing alone with the sea behind it, the Eastport Savings Bank building is a striking element of the downtown historic district. Now the home of the Tides Institute and Art Museum, the bank is another post-fire construction, when brick was in vogue because of its resistance to fire. A vintage account in the “Historical Sketch of Eastport” notes that the bank “has been and is of incalculable benefit to the wage-earners of the town. A savings bank is a benefit to any community, but particularly to one where work and good wages prevail for half the year and little work and less wages the other half” (as reprinted in the Border Historical Society Summer 2009 newsletter).

From the Eastport Savings Bank, your starting point at the farmers’ market is just up the street. Along the way, enjoy the many shops and galleries throughout the town’s historic district. The famous Fisherman statue by the wharf offers a fun photo opportunity, and the area affords excellent views of the harbor.