South Pleasant Street At first perhaps the most important street in town, Pleasant Street retained a prestigious residential character throughout the 19th century. This fact is witnessed by the range of styles present in the high quality buildings built for merchants and professionals along the street between Painter House and Cross Street.
71 South Pleasant Street Built in 1803 on a lot purchased from Gamaliel Painter by the brilliant young lawyer Loyal Case, an ardent reformer and opponent of slavery. It was Victorianized with Italianate brackets and mansarded tower probably in the early 1880s.
Memorial Baptist Church Built in 1905 – 06 to the designs of Burlington architect W.R.B. Wilcox, this handsome building with its Romanesque-derived towers succeeded the smaller church (now the Grace Baptist Church) on Merchants Row, built for the congregation by Smith and Allen of Middlebury in 1882. The new $75,000 church, constructed with textured rusticated marble blocks from the Brandon quarries of the Brandon Italian Marble Company, was the gift of Col. Silas Ilsley as a memorial to his father. The marble-lined vestibule contains two large bronze tablets identifying the donor and the reason for the memorial gift. Much of the building's interior displays a Gothic influence. The ceiling of the main auditorium as well as the lower portion of the walls are finished in antique oak, while the pews, of the same material, are decorated with elaborate Gothic designs. The actual construction was accomplished under the close supervision of Rev. George R. Stair, describing the Middlebury Register as an "extremely practical preacher who is a builder of structures as well as a molder of men."
111 South Pleasant Street Built in 1801 for the tanner Josiah Fuller across the street from his creek-side tannery and on the site of a house built by William Sloan in 1788. Beginning in 1818 it served as the home of Middlebury College presidents Bates and Labaree. A handsomely solid structure, it is notable for the Doric frieze below its eaves and the elegant Federal Style fireplaces in its north parlors. Oft-remodeled, it has received from its numerous owners a Greek Revival doorway and a gabled slate roof (placed over the original hipped wood shingle roof that still exists in the attic), a Doric-style portico (1970) modeled after that of the jail at 35 Court Street, and two back wings. The wing at the rear was added in 1991 and was designed to replicate the style of the original house.
135 South Pleasant Street Built in the 1860s for James Negus (on the site of the 1795 house of Oliver Brewster), this house is generally known as that of Governor Weeks, whose family occupied it in the first half of this century. Its belvedere, mansards, polychromed slate roofs, and elaborate brackets are exemplary of the local interpretation of the Second Empire (or "General Grant") style, which became popular in the years following the Civil War. The etched cranberry-colored glass around the door is another feature typical of Middlebury's finer homes in the third quarter of the 19th century.
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. Emma Willard occupied a room in this house when she first came to Middlebury to begin teaching at the Female Seminary on Seymour Street. 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 160 South Pleasant Street, and the sensitive window placement and beautiful attic light on the north end of the substantially proportioned 112 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 Rutland, Wallingford, Danby, Ludlow and Saxtons River. 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.