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 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.