I live and work in downtown Essex. Carson & Co jewelry studio is right here on Main St and one of the things I love most about the village is that its history is not confined to a museum. It is all around us, in the old houses lining Main Street, in the narrow lanes leading toward the river and in buildings that have served as homes, inns, shops, shipyard offices and warehouses for more than two centuries.
Essex is often praised for being picturesque, but its historic houses are more than a pretty backdrop. They tell the story of a working river town shaped by shipbuilders, merchants, sea captains, doctors, ministers and craftspeople. Between 1750 and 1900, more than 600 vessels were built in the Essex area, and many of the families connected with that maritime economy lived along Main Street and near the waterfront.
This walking guide begins near the top of Main Street, continues downhill toward the Connecticut River and includes a short detour along Pratt Street. Most of the houses are privately owned, so please admire them from the sidewalk and respect the privacy of the people who live there.
The Gamaliel Conklin House, 20 Main Street
The house at 20 Main Street is known as the Gamaliel Conklin House. Built around 1803, it is a handsome five-bay Georgian house whose balanced façade and central doorway give it the quiet symmetry associated with early Essex architecture.
Gamaliel Conklin was a partner in Conklin & Murray, a company involved in making spars—the long wooden poles used for ships’ masts and rigging. He was also closely connected with the Hayden shipyard at the foot of Main Street. The house is therefore a good place to begin our walk: even this relatively formal village residence was closely tied to the practical business of building and outfitting ships.
The Ezra Clark House, 25 Main St
Directly across the street, the Ezra Clark House, also known as the Clark-Stevens House, dates from around 1827. It was built by Ezra Clark on land that had previously been used as a cattle lot and was sold in 1831 to merchant Nathaniel Stevens.
The house is particularly interesting because it shows how Essex homes changed over time. Originally Georgian in character, it was later given Greek Revival details as architectural fashions evolved. During the twentieth century, architect Robert Carter added a rear gambrel-roofed section and restored the exterior clapboards.
It is easy to walk past a house like this and assume that it has always looked exactly as it does today. In reality, many Essex houses are layered buildings, altered by successive owners while retaining evidence of their earlier forms.
The Uriah Hayden III House, 24 Main St
Glance across the street again and you will find the Uriah Hayden III House, built in 1847. Its Italianate details make it noticeably different from the simpler Georgian and Federal-era houses nearby.
Uriah Hayden III worked as a merchant and bookkeeper, and the house reflects the changing tastes and increasing prosperity of Essex during the middle of the nineteenth century. Its design is said to have been influenced by the unusual Egyptian Revival Baptist church that once stood nearby. The house was altered during a 1927 remodeling, but it remains one of Main Street’s most distinctive residences. I love the red door.
The James Phelps House, 30 Main St
A little further down on the same side is the James Phelps House, built in the mid-1840s, is one of the finest Greek Revival houses in Essex. Its strong proportions, classical entrance and commanding position overlooking Middle Cove give it a more monumental presence than many of the village’s earlier homes.
James Phelps was a lawyer and politician who served in both state and national public life. The dignity of the house feels appropriate for a prominent nineteenth-century professional, but it is the quality of the architecture that makes the building especially memorable. It is regularly cited as one of Essex’s best examples of the Greek Revival style.
The house and gardens have also received more recent recognition for careful preservation and craftsmanship. It is a lovely example of how a historic property can continue to evolve without losing its essential character.
Maybe you can spot the copper-roofed cupola to the rear of the building?
Local’s tip: Take a photo at the entrance to Parker Lane. In early Spring you may be lucky enough to see the magnolias in full bloom. At other times of the year its just a beautiful vista.
The Dr. Ezra Mather House, 37 Main St
Across from the James Phelps house stands the Dr. Ezra Mather House, built in 1815. With its five-bay façade and restrained early nineteenth-century design, it has a calm formality that makes it one of Main Street’s most recognizable homes.
Dr. Ezra Mather moved from Centerbrook as the focus of local commerce shifted toward the increasingly prosperous riverfront village. The house remained in the Mather family until the 1950s, giving it an unusually long connection with the family for whom it was built.
The Mather House illustrates an important change in Essex history. As shipbuilding and maritime trade expanded, the center of economic and social life moved closer to the river. Main Street became the preferred address for many of the village’s leading families.
Local's tip: As you look at the house, notice the window on the lower left. It was previously a door and the entrance to the doctor's surgery via a discreet garden gate.
The Griswold Inn, 36 Main St
Although, not strictly a house, no historic walk through Essex would be complete without the Griswold Inn, affectionately known locally as “The Gris.”
The inn traces its business to 1776 and celebrates its 250th anniversary in 2026, making it one of the country’s oldest continuously operating inns. The present complex developed over time and includes buildings dating to around 1801, when Essex was a busy shipbuilding port.
The Griswold Inn has witnessed nearly every chapter of the village’s history. Sailors, merchants, shipyard workers and travelers once passed through its doors; today, it remains a gathering place rather than a building preserved purely for display. That continuity is part of what makes it so special.
Step inside to see the historic dining rooms and the extensive collection of maritime art, or stop for lunch before continuing down Main Street.
Local’s tip: The inn is especially atmospheric on a quiet weekday afternoon, when it is easier to notice the old rooms, uneven floors and maritime details.
The Richard Hayden House, 40 Main St
The brick house at 40 Main Street was built in 1806 for Captain Richard Hayden, an important member of Essex’s shipbuilding community. Its Flemish-bond brickwork and fanlight doorway make it stand out among the predominantly wooden houses of the village.
In 1896, the house became the rectory for St. John’s Episcopal Church, a role it continued to serve for more than a century. This long association explains why the property is sometimes remembered primarily as the Hayden rectory or former Episcopal parsonage.
Richard Hayden suffered substantial losses during the British raid on Essex in 1814, when vessels and maritime supplies along the waterfront were destroyed. His house is a tangible connection to the families whose fortunes were bound to the shipyards below.
The Noah Tooker House, 42 Main St
The Noah Tooker House, dating from around 1733, is believed to be the oldest surviving house on Main Street. Its center chimney, five-bay façade and timber-frame construction recall a much earlier Essex, before the village became a prosperous nineteenth-century port.
Noah Tooker was a shipbuilder, and archaeological investigation suggests that the house may have been moved and turned to face Main Street in 1812. It was remodeled during the twentieth century, but its early structure remains an important link to the first period of European settlement and shipbuilding in the village.
This is one of my favorite houses on Main Street and its also one of the most photographed as the quintessential New England dwelling. It does not announce its age dramatically, yet it has stood here through almost three centuries of change.
Local's tip: At night check out the gas lanterns in the garden.
The Ebenezer Hayden II House, 46 Main St
Built in stages during the late 1790s, the Ebenezer Hayden II House occupies an important position near the foot of Main Street. Its hipped roof and elegant fanlight made it unusually fashionable for the period.
Ebenezer Hayden II was part of the family that dominated much of the shipbuilding activity along the waterfront. The house’s location allowed its occupants to remain close to the shipyards, stores and wharves while living in a substantial and refined residence.
As you reach this part of the street, the concentration of Hayden family properties becomes especially noticeable. Main Street was not simply near the shipbuilding industry; it was the residential extension of it.
The Foot of Main, 48 Main St
At the bottom of Main Street stands the early brick building known as The Foot of Main. Constructed in the early nineteenth century, it originally served as a warehouse, ship’s store and chandlery operated by Samuel and Ebenezer Hayden.
A chandlery supplied ships with the equipment and provisions required before departure. During the British raid of 1814, merchandise was taken from the building. It was later converted into a residence, but its solid brick construction still gives it the appearance of a commercial waterfront building rather than a conventional village house.
The Dauntless Club
Next to The Foot of Main, near the waterfront is the historic Uriah and Ann Hayden House, which incorporated The Old Ship Tavern and is now The Dauntless Club.
Built around 1776, the house served as both the Hayden family home and a tavern. Uriah Hayden was a shipbuilder, and the Oliver Cromwell was constructed in the family shipyard immediately south of the property.
Together, however, the two buildings illustrate the Hayden family’s long presence in Essex and the way maritime business, family life and hospitality often occupied the same small area.
The Dauntless Club is a private members club dating back to 1906
The Dickinson Boathouse
The small building known as The Dickinson Boathouse was constructed around 1920 for E.E. Dickinson (a local businessman and factory owner who made witch hazel products). It replaced an eighteenth-century West Indies warehouse that had stood on the site since approximately 1753.
Although the present boathouse belongs to a later chapter in Essex history, its location preserves the connection between the village and the river. The earlier warehouse would have received and stored goods moving through Essex’s maritime trade, while the twentieth-century boathouse reflects the waterfront’s gradual transition from commerce and shipbuilding to recreation.
Essex Waterfront
At the bottom of Main Street, the village opens onto the Connecticut River. Today, it is one of the most peaceful places in Essex, but during the eighteenth and nineteenth centuries it was filled with shipyards, wharves, warehouses, timber, rigging and the noise of vessels under construction.
The Hayden shipyard stood here. In 1776 it launched The Oliver Cromwell, a 20-gun warship that was then the largest vessel built on the Connecticut River. The ship went on to capture several British vessels during the American Revolution before being taken by the British in 1779.
It takes some imagination to replace today’s yachts and lawns with stacks of timber and partially built sailing ships, but the waterfront is where the history of nearly every house on this walk comes together.
Local's tip: There is a model of The Oliver Cromwell hanging on the wall in front of the shop, Chocolate Geeks, in The Gris courtyard.
The Steamboat Dock and Connecticut River Museum
The large building now occupied by The Connecticut River Museum was constructed in 1878 by Phoebe Hayden, the widow of William S. Hayden. Known as the Steamboat Dock building, it served as a warehouse and general store at a time when steamboats were an important form of transportation along the Connecticut River.
Its conversion into a museum means that visitors can enter one of the waterfront’s genuine commercial buildings rather than merely viewing it from outside.
The museum is the natural place to finish the Main Street portion of the walk. Its exhibitions explain the river, shipbuilding, transportation and the War of 1812, providing context for the houses and families encountered along the way.
A Detour Along Pratt Street
Before or after walking to the river, take a short detour along Pratt Street. Running roughly parallel to Main Street, it is quieter and more residential, with houses placed close together along the narrow road.
Among the notable properties are the Gurdon Smith House, dating from 1818; the George Harrington House, built around 1815; the Smith-Hayden House, dating from the 1830s; and the Obadiah Spencer House, built in 1826. Together, they form one of the most appealing concentrations of nineteenth-century houses in the village.
One of Pratt Street’s most interesting stories belongs to The Jared and Isaiah Pratt House at 22 Pratt Street. The house was originally built on Main Street around 1803. It was substantially altered over time and moved to Pratt Street in 1923 when the site of the new Town Hall and Post Office was being prepared. Its Second Empire appearance disguises a much earlier building underneath.
Pratt Street is a good reminder that historic preservation does not always mean freezing a house at one moment in time. Essex buildings have been moved, enlarged, modernized and adapted, yet the village has retained a remarkable sense of continuity.
Where to Learn More
For a deeper introduction to Essex history, visit The Pratt House, operated by the Essex Historical Society. I have not included it as one of the stops on this particular walking tour because it is a museum rather than a private village house, but it is an excellent place to learn more about the people, buildings and industries that shaped the town.
The Essex Historical Society also operates Hills Academy and maintains collections, exhibitions and historical resources relating to all three villages of Essex.
Donald Malcarne’s books Houses of Essex I & II are valuable guides, particularly for anyone interested in individual house histories and architectural details. You can buy them in The Gris Goods store.
Essex Village recently applied to be on the National Register of Historic Places. The new historic district will cover Main Street, Pratt Street, Prospect Street and North Main Street and will help preserve the histories and architectural features of hundreds of contributing buildings within the village.
A Village Best Explored on Foot
The best way to appreciate historic Essex is slowly. Look beyond the storefronts, notice the old fanlights above the doors, compare the rooflines and think about how closely the houses are connected to the river below.
Some belonged to prominent families; others were occupied by the merchants and craftspeople who supplied the shipyards. A few have changed dramatically, while others still look remarkably close to their original form. Together, they tell the story of a village that grew around shipbuilding and maritime trade, and is still firmly centered around boating and the river today.
Essex is beautiful at first glance, but it becomes much more interesting when you know what you are looking at. Enjoy it.