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161 South Pleasant Street Built in 1822 by Peter Starr (on the site of the 1792 house of Festus Hill), this large frame home boasted a fanlighted Federal Style doorway and a fine series of fireplaces (since removed). It was remodeled (probably in the 1880s) with a new and steeper roofline and Victorian brackets and bay window. To the southeast of the house is a charming board-and-batten Gothic Revival carriage house. The Starr family were instrumental in the construction of two prominent buildings on the college campus—Starr Hall (1861) and Egbert Starr Library (1900).
190 South Pleasant Street A large frame house erected on one of the more prominent sites in town in 1800 – 01 for Joshua Henshaw, a director of the Vermont State Bank. In 1814 the bank was robbed of some $28,000 in what looked like an inside job. The next morning Henshaw left town for Canada, never to return, and subsequently a duplicate key to the bank was found concealed in the attic of his house. Later in the century the house earned a less notorious reputation as the Congregational parsonage. It was remodeled with a central pavilion (originally capped by a mansard tower), elaborate window frames, and enlivened roofline by Smith and Allen in 1882.
182 South Pleasant Street A house built in 1808 for Dr. Edward Tudor and subsequently owned by Harvey Bell, a lawyer, one of the first members of the Vermont State Senate, and long-time secretary of the Corporation of Middlebury College. The former elegance of this house is witnessed by the dentil cornice, the attic windows, the simple classical front door, the keystone lintels over the windows to either side of the door, and a fine parlor fireplace. Other houses on the west side of South Pleasant Street were built by tradesmen and are more modest. Though not as elegant as some of their neighbors to the east, they do preserve some of the fine details from the era in which they were built and suggest that the desire for quality was not restricted to those of large means: e.g., the handsome classical doorway (probably 1830s or early 1840s) of 6 South Pleasant Street, and the sensitive window placement and beautiful attic light on the north end of the substantially proportioned [14] South Pleasant Street (1806).
76 – 88 South Pleasant Street This house presents a definite change in taste. It was built in 1884 by Middlebury's influential Victorian architect, Clinton Smith, as his own home. Born in 1846, Smith began his building career as a carpenter in partnership with his father. In the 1870s he formed a building firm with William Allen, and they began a series of remodeling and construction projects in the area. In the early 1880s they purchased a mill in Frog Hollow to turn out the elaborate window frames, mouldings, and brackets that marked Smith's frame style, dominated the Victorian scene in much of west-central Vermont, and can be found up and down South Pleasant Street. At the same time Smith designed and Allen built a series of prominent masonry structures in the heart of town reflecting the latest tastes in such centers as New York and Boston.
Smith's own house incorporates these latter tastes in its complex but controlled massing, its combination of materials (brick, wood, slate, stucco), its craftsmanly delight in brick detailing, and its Stick Style porches with their turned woodwork. Built at the time that Smith was working on the neighboring Town Hall, the house gave rise to the story that contemporaries grumbled about the architect's using all of the best town bricks for his own project.
This Middlebury architect was prominent not only locally, but built structures from Montpelier and Waterbury to Wallingford and Rutland. His firm continued activity until the turn of the century, though he himself moved to Washington, D.C. in 1891, where he served until his death in 1905 as chief of construction and repair for the War Department. He is commemorated by a noteworthy monument in Middlebury's Foote Street burial ground.
Old Town Hall Built in 1883 by Clinton Smith on the site of Epaphrus Miller's fine 1811 brick house and tavern, which was removed so that the Town Hall could stand as a focal feature for those entering the town from the north on Pleasant Street. Here one meets the vocabulary of Smith's house used for a public structure. Described in contemporary accounts as being in a "modern" style, it is a vigorous building, with powerful asymmetric massing and a bold use of contrasting stone and brick. The brickwork itself is a mason's delight, creating flush patterns and sculptured textures to pick out and enliven various portions of the facade. The marble details not only emphasize certain elements of the building, but also serve to tie together the various masses. There were originally four cherry doors at the entrance, and the gaslit interior had a stage with an ash and cherry proscenium and a scenic curtain of the Gulf of Venice done after a painting by the English artist Stanfield. Further underlining the importance which the town attributed to this building was the historic cornerstone, containing records and memorabilia, set into the foundations by Henry Sheldon on June 15, 1883. Since that time town tastes, needs, and options have changed, and the building's status has altered with them. It was used variously as a furniture store and, until 1960, a movie theatre, its lateral Palladian windows being blocked for the purpose. The bell from the tower is now set in the garden of the Sheldon Museum.
Civil War Monument Presented to the town in 1905 by Col. Silas A. Ilsley, this granite monument stands at the head of Merchants Row over one of the old Middlebury fire protection cisterns (rendered obselete when a village water system was installed in 1902). It is said that this gift from a relative newcomer to the town spurred Col. Joseph Battell to present a counter monument, an elaborate cast-iron public fountain (removed in 1938 and replaced with a similar one in 1976) in the corner of the Green known as Triangle Park at the other end of Merchants Row.
Court Square Formed in 1785, Addison County had, at first, no permanent county seat. West Addison near Lake Champlain, the first proclaimed site for court sessions, looked like a prime contender, though Middlebury was certainly more centrally located. Soon after deciding to move to his property at Middlebury Falls, the canny Painter decided to tip the scales a little in favor of his intended town. He deeded a lot, just north of his own house and fronting or the line of Pleasant Street, to the County, and his persuasion seems to have worked. In 1790 Middlebury was proclaimed shire town of the County.
The first construction in the area now known as Court Square was a wooden jail built in 1794 (moved in 1812 to [5] Washington Street and subsequently remodeled as a residence and law offices). In 1796 work began on the courthouse itself. Not elaborate, it was nonetheless an impressive structure for the newly settled region. Without, it was a large, simple two story block with a belfry and fan window in its gable as its only embellishments. Within, it had one large room with a coved ceiling, a sloping floor with benches and a rear gallery. Noble but Spartan, it was reputedly very uncomfortable and cold, and the court preferred to continue meeting in an adjacent tavern. Not that the courthouse wasn't used. The state legislature met there in 1800 and 1806. In 1800, as well, Miss Ida Strong opened her female seminary, the feminine counterpart to the Addison County Grammar School, in the cold courthouse. The Congregational Society was a regular user of the hall until their church across the green was completed in 1809, and the Episcopal Society met there from 1810 – 1815.
Another of Painter's schemes for Middlebury ran counter to the placement of the courthouse, however. This was the development of the Centre Turnpike, a stage route down what is now the line of Highway 7 to East Middlebury, across Middlebury Gap, and on to Woodstock, where it connected with stages to Boston. Begun in 1799, the new road entered the village on what is now Court Street and terminated at the back side of the courthouse. Accordingly, the building was moved across the street onto more Painter-donated land in 1814, and its old site became Court Square. In 1829 the building was divided into two more-heatable floors, the upper continuing as courtroom, the lower serving as town hall. Repaired and remodeled in 1844, it was determined inadequate and old fashioned in 1882 and moved to the Addison County Fair Grounds (now the recreation park) down Court Street, where it served variously as a harness shop and floral hall until it was torn down in 1939.
Its replacement, by Clinton Smith of Middlebury, was described in the Middlebury Register in 1883 as of "mixed architecture with Queen Anne features," and declared the handsomest courthouse in the state. The facade is both picturesque and ordered. Its asymmetric massing and variety of detail in stone, brick, wood, slate, and glazing are held in line by articulating brick panels and "structure." This was very up-to-date design for Vermont. The panel-brick style (as it since has been dubbed) was just being popularized by leading architects in Boston, New York, and Philadelphia. Yet the courthouse is hardly a pure import. Its architect is local, and he has put the stamp of his personality and craftsmanship on its design. He also has maintained a sensitivity to its setting. Vigorous in its detail, the courthouse remains a good neighbor to the earlier structures on Court Square, prominent, but not too assertive for the good of its surroundings.
Among its neighbors, the house to its right with the elaborate center chimney was built in 1825; the Masonic Hall to its left was built in 1823. By the 1990s, the 1883 courthouse was considered to be inadequate and a new courthouse, named after Judge Frank Mahady, was constructed on a more spacious site behind the previous one in 1995 – 96. The new building features a hipped roof, a central cupola and a pedimented entry bay. The old courthouse, no longer used by the court system, passed to the ownership of Middlebury College in accordance with provisions in Painter's deed.
Middlebury Inn On the north side of Court Square and serving as a focus for travelers entering the town on the old Centre Turnpike (Court Street) is the Middlebury Inn. Painter had deeded this prime site just north of the court lot to Simeon Dudley in September of 1788 for the construction of a tavern, but Dudley did not carry through. In 1794 Samuel Mattocks did, however, building a tavern that stood on the site until a fire destroyed it and neighboring structures in 1816. The brick house of Nathan Wood [(on the Knights of Columbus site)] served as an interim tavern until Wood rebuilt on Mattock's lot in 1826. Wood's new inn, the Vermont House, was a grand three-story brick building with fifty rooms. Since its opening on April 16, 1827, the inn has changed its name twice (Vermont House 1827 – 52; Addison House 1852 – 1927; Middlebury Inn 1927 – present), been Victorianized and un-Victorianized (1851, 1865, 1897, 1927), and grown considerably. Once it had a cupola, later a wrap-around piazza, and later still was painted yellow. Indeed, perhaps the only bit of the original building other than the basic masonry of the main block to survive all the changes is the fan-lighted doorway with elliptical carved decorations looking out onto Pleasant Street and the Green. The basement and part of the first floor have housed at times office stores, a barber shop, and the Middlebury Post Office. For all the changes, however, the building has a continuous history of service to the town as its principal inn and a favorite meeting spot since Nathan Wood's day.
North Pleasant Street Running northward from Court Square, Pleasant Street was originally known as the New Haven Road and served in earlier times as it does now as the principal entry to the village from the north. Here were located from the start the homes of the professionals who would bring status to Middlebury and the craftsmen who would supply the town's needs for quality goods. Here, adjacent to the Green, Painter quickly deeded lots to such people as a lawyer, a doctor, a cabinetmaker, and a blacksmith. In time a series of quiet elegant buildings were constructed in the area.
23 North Pleasant Street This fine brick structure was built in 1816 as a store for Thomas Hagar and subsequently housed the National Bank of Middlebury until its move to new quarters across the Green in 1910. The second floor was occupied for many years by the predecessor of Middlebury's public library, the Ladies' Library, founded in the 1860s. In the course of its history the building had a balustraded roof line; first a Federal, then a Greek Revival, and then a Victorian doorway; and shared with the inn a beautiful stretch of cast-iron fence toward the Green.
Inn Annex The brick house just north of the Inn and bank was erected in 1825 for Jonathan Wainwright, whose brother Rufus purchased the Painter mansion not long after Gamaliel's death 1819. The brothers were merchants and owned a foundry, first in Frog Hollow and later near Pulp Mill Bridge, where they cast (among other things) the widely-sold Wainwright stove. Jonathan's house was both substantial and soberly elegant with its great brick mass, even rhythm of windows, and beautifully proportioned and detailed doorway. This last is noteworthy for its fine leaded fan and side lights and its sophisticated combination of pilasters and colonnettes. Beyond this doorway are to be found moulded ceilings, paneled window embrasures, classically detailed marble fireplaces, and one of Middlebury's finest curving staircases. In 1881 Smith and Allen remodeled the house, changing the gabled roof into a fashionable Second Empire mansard and adding the Palladian window, the bay window toward the inn, and the dominating piazza. The house remained a residence for prominent Middlebury families until its purchase in 1941 as an annex for the inn.
Charter House In 1789 Painter deeded a lot on the New Haven Road (just north of the later Wainwright House) to Samuel Miller, a lawyer from Springfield, Mass. Here Miller built first a small law office and then his home. Not only a leading and reputedly very courtly lawyer, but also representative to the General Assembly in 1797 and recipient of an honorary degree from Yale, Miller was a prominent participant in the affairs of his new town. On September 30, 1798, he was host to a meeting in his home that was to have long-lasting significance to the community. Timothy Dwight, president of Yale, was stopping off briefly at the home of his friend, the Middlebury lawyer Seth Storrs. Storrs quickly gathered the trustees of the newly chartered Addison County Grammar School, and in conference at Miller's house and with Dwight's advice and encouragement, they determined to apply for a charter for Middlebury College. As a result the house came to be known as Charter House.
A building much altered and augmented, Charter House seems to defy precise dating and discussion. The 1789 law office was most likely shifted to the rear to make room for the newer front structure of the 1790s. This had a hipped roof, which still exists beneath its mid-century gabled slate roof, and most likely a center chimney and a straight-headed Palladian window. After Miller's death in 1810, the house was purchased by Edward D. Barber, who purportedly altered it extensively. Under Barber and later owners it received its mix of fine Federal, Greek Revival, Victorian and Colonial Revival details. Particularly noteworthy are the leaded glass of the front dour, the beautiful fireplaces with eagles, urns, and swags in the front parlors, and the fine interior door casings. In 1970 the house, which had fallen into sad disrepair, was purchased by the Congregational Church, laudably renovated, and restored to a significant place in the life of the community.
31 North Pleasant Street To the north of Sam Miller was originally the lot of Dr. Matthews, and to the north of that a double lot originally deeded to William Young, Middlebury's first cabinetmaker. On this latter site, in 1805, was built the house of lawyer, businessman, selectman, and college officer John Simmons. A graduate of Brown University, Simmons established his Middlebury law practice in 1801, and in 1804 compiled The Law Magazine, the first book of legal forms ever published in Vermont.
His house is significant both for its plan and for its elegant detailing. The typical prestigious residence of the eighteenth century had been broadside to the road with a central doorway, either a central chimney mass or center hall, and major rooms to either side. Simmon's house is an early example of a more townhouse-like plan that would become popular in Middlebury in the first third of the nineteenth century. It is arranged with its narrow, or gable, end toward the road. An off-center entrance and staircase occupy a front corner of the house, and chambers are arranged to one side and the back of a central chimney mass. The gable is treated as a pediment and decorated with fine rope and lentil mouldings. Set into it is a gracefully-muntined elliptical attic window with a star-shaped central decoration. The doorway (beneath the Victorian porch) is typically deep-set with paneled returns and a semicircular fanlight. Within are three of four very fine original fireplaces with lentils, sunbursts, and pilasters, and beneath the first floor windows is a series of framed panels which a later resident painted with lovely impressionistic landscapes. Not as grand, perhaps, as the Painter and Wainwright houses, it was without a doubt one of Middlebury's most sophisticated residences.
37 North Pleasant Street This Federal-Greek Revival style house, built in 1803 by local merchant Joseph Dorrance, on a site previously owned by Cyrus Brewster, later became the residence of Vermont governor William Slade. The main features include a Georgian porch, sidelights, transom, paneled entry pilasters, entry entablature and a Queen Anne porch.
39 North Pleasant Street One of Middlebury's few surviving early hipped-roof houses, this structure was the first (1804) of three houses in the neighborhood built and lived in by blacksmith Ruluff Lawrence. His first house was built on the site of a 1793 home of Dr. Joseph Clark which was moved to Seminary Street. Much altered inside, Lawrence's two-story Federal style house still has a staircase which agrees in detailing with his 11 Seminary Street house. Other features include a Georgian plan, leaded glass, sidelights, transom, cornice caps, and a distinctive porch.
Methodist Church In 1805 Hastings Warren purchased this lot from Daniel Chipman and built a cabinet shop. Warren was the son-in-law and successor in business to William Young, Middlebury's first cabinetmaker, and pursued his trade well into the 19th century, filling the local papers with ads for "sideboards, commodes, secretaries, bookcases, bureaus, wardrobes, tables, chairs, clock-cases," etc. The Henry Sheldon Museum contains interesting examples of his fine work. During the war of 1812, Warren, who achieved the rank of General, mustered and led the local troops for the Battle of Plattsburgh. As recounted in Swift's History of Middlebury:
"He came on to the village common, followed by martial music, and invited all who were so disposed to join him as volunteers. After marching once or twice around the common, forty or fifty men had fallen into the ranks, and the number was afterwards increased. When a dozen or two were ready to start with him, they marched for the field of battle, and others, as fast they were ready, followed."
Warren's first shop burned, as did its successor. In 1815, therefore, he went "fireproof," building a fine two-story brick structure next door (9 Seminary Street—demolished in 1975).
He was among the earliest members of the Methodist Society in Middlebury, and it is probably through his connection that in 1837 the Society gained possession of the Pleasant Street site for its new frame church. This building burned in 1891 and was replaced by the present structure in 1892 – 93. The plans for this building were drawn by Valk and Son of Brooklyn, N.Y.; but not entirely satisfying the congregation, they were altered by Clinton Smith, whose firm of Smith and Piper built the edifice. It is a fine example of late Victorian architecture and much under the influence of the work of Henry Hobson Richardson with its combination of gray and brown stone, brick, and slate, its vigorously massed tower, its strongly expressed stone base from which rise swelling brackets to "carry" the load of the dominating roof, and its Shingle-Style, slate-covered gable ends. It is a design in which materials and forms are used with vigor and unity to express emphatically the forces at work in the architecture. Essentially intact down to the non-figured stained glass of its windows, the building is one of the best examples of quality late Victorian architecture in the Champlain Valley.
Cross to the west side of North Pleasant Street and head back towards the center of the village.
32 North Pleasant Street Across the street and partly concealed by a later layer of stucco and pebble masonry, is another interesting old house. It was built in two sections—the earlier, southern half by Loudon Case, the later northern half by Olcott White in or soon after 1807 to house his book bindery and shop. The lentil moulding beneath the eaves, the attic window, and the handsome chimneys bespeak the former quality of this building.
Congregational Church The prominent site at what is now the intersection of Main, Seymour, and North Pleasant Streets was not always that of the Congregational Church. It was originally deeded by Painter in 1789 to John Deming for the construction of a blacksmith shop and tavern. Painter himself helped to underwrite the cost of this latter, a two-story building which could accommodate twenty-five guests at a time and served as seat of the Addison County Court both before and after the construction of the courthouse.
Where was the church then? The location of the church had been a principal feature of the long-lasting feud between Painter and Daniel Foot. Painter wanted it at the falls, Foot wanted it near his homestead at the center of town. Each side had its strong supporters who threatened to withdraw if the conflict were not resolved to their satisfaction. At the town meeting of 1788 Foot's barn had been chosen as the best available site for worship, and in 1790 a site committee voted three to two in favor of a meetinghouse location near Foot's homestead. The two were Painter and John Chipman, and they managed to block the final decision, so much to Foot's anger that he withdrew the use of his barn and eventually became a Baptist. In 1794 worship moved out of Middlebury's barns and into the newly completed Mattock's Tavern, where it stayed until the completion of the suitably uncomfortable courthouse in 1798. By 1806 there was little question as to the location of the functional center of town, and Daniel Foot had moved on. Painter finally convinced his townsmen and picked the site at the head of Main Street. The lot was purchased from current owner Loudon Case, the tavern was moved down Seymour Street (and demolished in this century), and the town finally prepared to build its church. It was a bit embarrassing. There was Middlebury, a sophisticated and increasingly attractive and important town with mills, stores, fine homes, inns, a courthouse, and a college—but still no church. The embarrassment was remedied, however, by the construction between 1806 and 1809 of a church the town could never have considered in 1790—one of the finest Federal style churches in New England.
As head of the building committee Painter called on Lavius Fillmore, a Connecticut-born house joiner who had moved to Middlebury in 1796 and had built four previous churches (East Haddam, Conn., 1794; Middletown, Conn., 1798; Norwich, Conn., 1901; Bennington, Vt., 1804 – 06) and, especially in the Bennington area, a series of magnificent houses. The Middlebury church was to be Fillmore's masterpiece. Three years in the construction, budgeted at about $9,000 (some fifteen per cent more than the Bennington church), and financed by the sale of pews for cash, building materials, and livestock, the building was similar to but larger and more elaborate than its Vermont sister. The general mass of the church is based on meeting houses built by Charles Bulfinch in Taunton and Pittsfield, Mass. in the late 18th century. Fillmore's early refinement of this type in East Haddam so influenced the design published by Asher Benjamin in his 1797
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