1 South Street The classicism is more pervasive next door to Storrs' house in that built for George W. Cutter about 1837. Here the broadside plan has been avoided in favor of the Federal townhouse type (e.g., Simmons House, 31 North Pleasant Street). In the latter the gable oriented toward the street permits something more akin to a temple-like mass for the house. Middlebury's Greek Revival never went all the way with columnar temple porticoes but it can be seen embodied here in the elaborately designed doorway with its wooden pilasters and palmettes and its cast iron tracery. Later in the 19th century a large porch extended across the entire front of the house and around the south side as far as the bay windows. It was removed in the 1950s.
3 South Street ("The President's House") This house was built in 1854 by Jason Davenport, successor to the Wainwright foundry business. In order to locate his home as closely to the center of things as possible, Davenport moved the previous house on the site (that built in 1797 by Dr. Darius Matthews) to its present location at 13 South Street. The 1854 house is one of Middlebury's few examples of Carpenter's Gothic, a popularization of the Gothic Revival stressing pointed gables and inventively intricate wooden cut-out decoration for eaves and (as on the Davenport house) porches. Here the bargeboards under the eaves have disappeared over time, but there are still the drip mouldings on the windows, and the porch is treated as a series of flattened pointed arches, reminiscent of Gothic arcades. Since 1918 this house has served as the home of the Middlebury College Presidents.
5 South Street The parade of 19th-century styles continues down South Street with number 5, built in 1870 and for a long time the Episcopal parsonage. Here one finds a classically-derived doorway, Gothic-derived sharply pitched roof and asymmetrical massing, Italianate eave brackets and a large Victorian piazza and bay window.
7 South Street Similarly eclectic, if also perhaps more high fashion, were the house and barn built just to the south by Governor Fairbanks, originally of St. Johnsbury, in 1867. A mix of French concave mansard roof and quoins with Italianate brackets and arcaded porch, its was one of the most elegant and dignified Victorian homes in Middlebury. It is now owned by Middlebury College.
95 South Main Street A few steps back to the intersection of South and South Main Street brings one back to the early 19th century, with the Blinn House. A small house built around 1800 existed on the site when Blinn moved here in 1810. The new owner shifted the original house back to the southwest corner of the lot, where it is now 97 South Main Street. He then built a far grander two-story house to replace the original. The rear ell was probably added by a later owner. The Blinn House is now owned by Middlebury College.
Municipal Building (Town Hall) Across South Main Street from the Blinn House on a site referred to in earlier times as Storrs Park is the Municipal Building (formerly High School). The Municipal Building is located the site of an old brick school house. The earlier building was sold in 1869 to Eli B. Parker for $335, and Parker took it down, reserving the brick, stones, and bell for the School District, and probably using some of the timbers in the construction of his own house at 57 Seymour Street. In 1911 the site was filled with Middlebury's new high school (the gymnasium and auditorium behind being added with Federal funds in 1938 – 39). Constructed somewhat in the style of the great 19th-century architect H.H. Richardson, the brick building originally had two floors with great brick arches over the entrance and the second floor windows and a powerful dormered roof pinned down by four massive chimneys. For forty-three years it served as a counterpart to the church at the other end of Main Street. The upper portions of the structure were destroyed by fire in 1954; and after the construction of a new union high school off Court Street, the refurbished basement and first floor of the old school became home for Middlebury's municipal offices.
Academy To the west of the present day Municipal Building was a structure as important to the life of Middlebury as was the church at the other end of the street—the Academy. Middlebury's children were given a rough and rudimentary education in "common schools" meeting around town, usually in people's homes; but Painter and others wanted more, a school that would carry on beyond the fundamentals. With Storrs, who had experience in secondary education, Dr. Matthews, and lawyers Daniel Chipman (founder of the first law school in Vermont) and Samuel Miller, Painter formed the Addison County Grammar School Corporation, chartered by the legislature in November of 1797. Storrs and his neighbors assembled and donated a sizeable school lot and common (the west side counterpart to Painter's Green) and $4000 were raised by public subscription for the 1798 construction of the Academy building.
The wooden building was forty by eighty feet and three stories high, the largest structure yet built in town. Similar to (if simpler than) Dartmouth Hall in Hanover, N.H., in character, it had an impressive number of windows (glass was very expensive), equally important front and rear entrances, and a crowning cupola. The first floor held classrooms, library, and laboratory; the second, dormitories (accommodating two to three students per room); and the third dormitories about a central chapel.
Upon the founding of the College in 1800 the building housed both College and Grammar School until 1805, when the latter was moved into the then vacant building of the Female Seminary on Seymour Street. The Grammar School moved back in 1844 and in the 1850s merged with Middlebury School District no. 4.
In 1867 the Academy Building was superseded by a new building located just slightly to the west, a fashionable Italianate structure designed by J.J.R. Randall of Rutland. Of brick with brownstone details, the building had heavy, bracket-supported cornices, a gable centered on each facade, and an elaborate mansarded cupola. A fire on Easter in 1904 gutted the school, but it was rebuilt with only slight changes to the roofline (and the elimination of the cupola), and it long served the town as the College Street Graded School. In 1984 it was acquired and renovated by Middlebury College, at which time it was renamed Twilight Hall in honor of Alexander Lucius Twilight of the Middlebury Class of 1823, the first African-American citizen to graduate from an American college, who went on to become a distinguished clergyman, educator and legislator in Brownington, Vt.
In a way, the location of Twilight Hall adjacent to the Municipal Building is quite suitable, for it was here traditionally that the two faces of Middlebury, town and gown, met. Here the bustle of commercial Middlebury leaves off and the academic world that for so long as been Middlebury's other half takes up.