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Court Street
9 Court Street A house of 1823 completely transformed by an elaborate Victorian remodeling in the 1880s. The bay windows, porches, brackets, fascias under the eaves, and dormers are quite typical of the woodwork from Smith and Allen's Mill Street shop. The Second Empire mansard roof and tower exhibit particularly fine multi-colored (polychrome) state work, popular in the Middlebury area during the Victorian period.
12 Court Street Built in 1827 by Nahum Parker as a cabinet shop, this is reputedly the shop in which the Brandon-born Stephen A. Douglas learned his trade.
13 Court Street Built in 1796 by Erastus Hawley at the corner of Court and Washington Streets and moved about 1828 by Nahum Parker for his residence. It has been substantially remodeled for retail purposes.
15 Court Street The old Middlebury Hotel, built in 1811 (and much remodeled) adjacent to the old Addison County Fair Grounds (now the Recreation Park). Just to the south of this is the site where the 1796 courthouse stood until 1939 as an exhibition building for the fair.
31 Court Street The delightfully elaborate Victorian remodeling (1881) of an 1810 Cape Cod house.
35 Court Street The 1846 Addison County jail, third jail to be built in Middlebury. It is a fine brick structure in a simple Greek Revival taste. Until the 1960s the cells were completely lined with slabs of Brandon marble. Changing penal patterns in the state led to the closure of the county jail in 1971 and then to its reopening with some renovations in 1984. In 1996 an expansion was designed and built by Breadloaf Construction Company, with a renovation of the cell block to increase the number of cells from 12 to 21 and the addition of a sally port, day room, and an exercise court.
Washington Street
7 Washington Street Middlebury's first jail (1794), moved to this site from Court Square in 1812 and remodeled first for use as a dwelling and later as offices. The cells originally had walls of stout planks ribbed with wrought iron rods stapled to the planking.
15 Washington Street Early 19th-century blacksmith shop, repaired in 1815 by John Houghton, now a residence.
17 Washington Street Middlebury's second jail, built by Jabez Rogers in 1811. This handsome stone building was converted into a residence in the 1840s by Oliver Wellington with the addition of the back ell and some fine Greek Revival details. The lights around the front door are set with an uncolored variant of the etched glass that was popular in Victorian Middlebury.
27 Washington Street Site of the small 1801 house of Samuel Coe, one of Middlebury's first and reputedly finest house joiners. Coe was murdered here, and his heirs sold the property to Elisha Brewster, who had the front two-story structure built in 1815. The old back wing, thought to be haunted, was supposedly removed and replaced. Brewster's was a Federal Style townhouse, oriented end-on to the street and detailed with an elliptical attic light and some of the finest cave mouldings in Middlebury. The Greek Revival porch, doorway, and tall first floor windows are the results of a remodeling of the 1840s. In the side yard was located one of Middlebury's old fire protection cisterns.
30 Washington Street Nathaniel Ripley House, about 1815.
36 – 38 Washington Street Leonard Deming House, 1810.
51 Washington Street The Deacon J. Erwin Crane residence. This structure was built by Clinton Smith in 1881 with a wildly eclectic use of the popular styles of the day. Here elements of French, Italian, and Gothic Revival mix and blend to make one of Middlebury's most remarkable Victorian houses.
53 Washington Street This cottage, built in 1871 for Sylvester B. Rockwell, a wealthy sheep merchant, who owned nearby "Springside" at 39 Seminary Street, is a charming example of Carpenter's Gothic, which was popular in Vermont through the middle decades of the century.
68 Washington Street Extension Built by Clinton Smith for Luther Farnsworth in 1882, this is one of Smith's most delightful and elaborately detailed creations in wood. Particularly noteworthy are such Stick Style elements as the pseudo structure of the tower and dormer and the elaborate brackets of the porches.
Washington Street Extension Burial ground used in the last years of the eighteenth and early years of the 19th century by village families. Here can be found members of the Painter, Simmons, and Miller families.
Seminary Street
11 Seminary Street Built by Ruluff Lawrence in 1810, this house boasts a center hall with a curving staircase and twin chimney masses that merge in the attic. Its front door was later remodeled in the Greek Revival Style.
12 Seminary Street Built on the site of 39 North Pleasant Street by Dr. Joseph Clark in 1793 and moved by Ruluff Lawrence in 1804.
15 Seminary Street Built by Ruluff Lawrence in 1808 on land purchased from Daniel Chipman. This house has the unusual feature also seen in 11 Seminary St. of twin chimney stacks merging in the attic into the single mass that penetrates the roof. The house has been divided down the center and altered accordingly.
21 Seminary Street Built in 1813 by Middlebury printer Timothy C. Strong, publisher of the Vermont Mirror, the Christian Herald, and the Christian Messenger.
23 Seminary Street Built in the first quarter of the nineteenth century for Samuel Bent, manufacturer of candles, starch, and wool cards.
26 Seminary Street Built about 1804 by William Baker for Loudon Case. At mid-century it was the residence of Joseph Dyar, Middlebury silversmith and clockmaker.
33 Seminary Street Former District 6 Schoolhouse, built in 1823 and converted into a residence in 1872. The doorway with its etched red Victorian glass originally came from 11 Washington Street.
39 Seminary Street "Springside." This is the site on which Daniel Chipman, a cousin of John, had his frame residence built in 1802 – 03 according to the designs of Samuel D. Coe. Chipman settled in Middlebury in 1794 to practice law. From 1798 onwards he frequently represented the town in the General Assembly, in 1813 and 1814 served as Speaker of the House, and in 1814 was elected to Congress. Early in the century he founded a law school, for which he built a three-story building across the street from his home in 1816. In 1818 the great house, reputedly the most beautiful in Middlebury, burned, and the Chipmans took up residence in the law school and later moved to another fine house Daniel had built in Ripton.
In 1832 Epaphrus Miller bought the Chipman site and in 1836 had the present structure built. Surrounded by broad lawns and a fine wrought iron fence, it sits prominently on the southern slope of the hill, a great brick mass with handsome Greek Revival details and porch. In 1853 the property was purchased by wealthy sheep merchant Sylvester B. Rockwell, who added wide sliding doors between the front and back parlors, red and blue Bohemian pressed glass around the door, and the wooden wing behind the house. Rockwell's granddaughter married Professor (and later President) Ezra Brainerd, and the home became the president's house between 1885 and 1907, with Monday evening faculty meetings held in the front parlor.
Besides its site, its grand rooms and fine woodwork, the house boasts a large kitchen fireplace with two ovens and a basement spring which served as a natural refrigerator and from which the property takes its name of "Springside."
42 Seminary Street It was on this site that Daniel Chipman built his three-story law school, to which he moved after the 1818 fire in his home. In 1827 the Female School Association purchased the building and fitted it up for the Female Seminary (from which the street took its name). A two-story wing was added three years later. In 1869 Charles Munroe bought the property and, according to conflicting accounts, variously razed, moved and remodeled portions of the Seminary complex to develop the property for his residence. In 1925 the Munroe house was enlarged and remodeled into the present Colonial Revival structure. The building served as the Congregational parsonage from 1946 to 1975.
Stonecrop Ledge (Seminary Street Extension) This lot was settled in 1784 by Stephen Goodrich, who built first a cabin and then (about 1797) a house on the site. In 1800 he deeded his house and fifty acres to Dr. William Bass, a young and soon-to-prosper physician. Here by 1812 Dr. Bass had built one of the most prestigious houses in Middleburv. Its broad western front with its Georgian central pediment, Palladian window, and grand fan-lighted doorway was designed to be seen from Washington Street; but its operative entrance was toward Seminary Street, from which it appeared to be a large version of the Federal Style townhouse. The mass of the house is heightened and rendered even more impressive by the high attic with its series of fine elliptical windows.
Within, this house is of the "townhouse" type, with an off-center entry and curving staircase. The walls of the principal rooms have been thickened to permit the paneled window recesses usually possible only with masonry and the fireplaces have mantles of varied and elegant Federal Style designs. Elements of the house relate so closely to the Congregational Church and the S. S. Phelps House on Main Street that it is inconceivable that this could be the work of anyone other than Lavius Fillmore. The house was later acquired by Prof. D. Gregory Means, who added the elaborate porch to the west front and the winterized back apartments.
The stuccoed house across the street from Stonecrop Ledge, at 62 Seminary Street Extension, is reputedly a section of the Female Seminary moved from the Munroe House site and converted into a residence. If so, it is the only element of the three buildings in town occupied by the Seminary to be left standing.
East of the Seminary building, at 66 Seminary Street Extension, is the Asa Chapman House, built at the corner of Court and Washington Streets in 1800 as Erastus Hawley's harness shop. It was purchased by Chapman for use as a shop and then remodeled as a dwelling in the Greek Revival Style. It was moved to the present site to make way for the building of the Chittenden Bank on Court Square.
High Street
4 High Street This much added-to story-and-a-half dwelling was built about 1815 by Martin Wood.
8 High Street Built in 1815 by Rowland Hack, this simple two-story postcolonial house has received a later doorway with etched glass lights.
11 High Street In spite of its added dormer and porch, this house, built about 1810 by Josiah Stowell, is one of the best preserved Cape Cod houses in Middlebury. Behind its large and very complete old kitchen fireplace is a smoke chamber, above which climbs the tiny, steep staircase to the upper floor.
17 High Street Another interesting and well-preserved post-colonial house is this one begun as a one-story, center-chimney dwelling by house joiner Bela Sawyer in 1798. Later owners added a full second story, Greek Revival door surround, and back wing, but the south front of the house (toward Seminary Street) maintains a staunchly late eighteenth century scale and air.
18 High Street The story-and-a-half dwelling built by Nathaniel Ripley, one of Middlebury's early carpenters, about 1800.
Stewart Lane
The entire north side of this street, carved from Daniel Chipman's estate in 1814, is occupied by the property and home (built 1814 – 15) of Samuel Swift, lawyer, town clerk, state legislator and local historian. Here in 1855 Swift wrote the minutely detailed History of the Town of Middlebury, on which much of the information in this booklet is based. Slightly less grand in scale and detailing, the house is very similar to Stonecrop Ledge of Seminary Street in form, though it was oriented solely toward Stewart Lane. The interior was somewhat altered (with the removal of the curving staircase) and a summer kitchen wing was replaced by a two-story back ell by Governor John W. Stewart. For Stewart as well Clinton Smith designed and built the 1885 horse barn and carriage house at the northeast corner of the property. The house remained the residence of his daughter, Mrs. Charles M. (Jessica Stewart) Swift, in whose person are represented four of Middlebury's most important families—Seymours, Battells, Stewarts, and Swifts—until her death in 1982 at the age of 110. The house and carriage barn have subsequently been converted into the Swift House Inn.
North Street
1 North Street A one-and-a-half-story house built in 1810 by Clark Fitz. This simple but attractive post and beam structure has sidelights and a distinctive door.
Methodist Lane
3 Methodist Lane Almost certainly the home of William Young, Middlebury's first cabinetmaker. Built about 1796.
Weybridge Street
70 Weybridge Street "The Homestead." Built in 1809 far Samuel Sargent, a goldsmith, who may also have added the Greek Revival door and interior woodwork before his death in 1847. The house is now owned by the College.
53 Weybridge Street The 1813 home of Artemas Nixon, one of the succession of operators of the Mattocks Tavern on Court Square.
82 Weybridge Street "The Gables." A residence of the 1880s mixing Gothic Revival and late Victorian tastes. The tower above the door has been truncated.
73 Weybridge Street Built by Benjamin Lawrence in 1810 and Victorianized by Clinton Smith for Dr. Merritt Eddy in 1878.
107 Weybridge Street Site of the 1810 Federal Style house built by Benjamin Lawrence and inhabited by Dr. Z. Bass. The original house was moved back on the site and converted into a carriage house in 1883 to make way for M. L. Severance's Second Empire Home.
202 Weybridge Street Built by Jonathan Hagar in 1818, this Cape Cod house was subsequently remodeled in a Gothic Revival taste. With its gingerbread porch and verge boards, it is one of the most charming examples of Carpenter's Gothic to be found in the Middlebury area.
256 Weybridge Street Also built by Jonathan Hagar in 1818, but unlike its contemporary at number 202, this house has retained its original character to a remarkable degree. With its fine proportions, stocky center chimney, beautiful Georgian style doorway, and kitchen fireplace, it is one of the best preserved of all early Middlebury homes.
275 Weybridge Street The home built for tanner David B. Nichols, probably in the late 1830s, is the most complete example of Greek Revival architecture to be found in Middlebury. Noteworthy are the beautifully detailed front doorway with its delicate colonnettes, the corner pilasters with inset palmettes, and the rectangular attic window with its elaborate frame. Within, the woodwork of each major room has been decorated with a different motif.
South Street
Porter Medical Center and Helen Porter Nursing Home At the edge of the village is the Porter Medical Center, established by a gift of William H. Porter in 1923 to provide a complete medical facility for the college and the community. This complex of buildings has been expanded and modified many times over the year.
South Main Street
Main Street Burial Ground To walk this burial ground is to walk Middlebury's past. Here beneath simple slabs, eternal obelisks and pyramids, and a sublimely shattered pillar rest some of the most prominent persons from every era of Middlebury's history: Gamaliel Painter, Seth Stows, Horatio Seymour, Eben Judd, Daniel Chipman, Samuel Swift, Henshaws, Starrs, Battens, Wainwrights. Not far from the grave of Daniel Chipman and just next to that of General Hastings Warren is the monument (on the Mead lot) of Prince Amun-Her-Khepesh-Ef, two-year-old son of King Senwoset III and Queen Hathor-Hotpe [sic], who died in 1883 B.C. In Middlebury? No, but his mummy was on display in the Sheldon Museum until the damp Vermont climate triggered its deterioration and it was decided to give the Prince decent burial once more, trading the Champlain Valley for Egypt's Valley of the Kings.
Ethan Andrus House On the west side of South Main Street (Route 30) across from the field house complex. This house, built for Ethan Andrus in 1803, is one of the handful of very early high style houses in Middlebury. The two-story residence is particularly noteworthy for the dentil moulding beneath its eaves and the elegant Georgian detailing of the front door, its pilasters and pediment very similar in conception to those of the main door of the Congregational Church. The house is now owned by the College.

In the Town
Farmingdale (the Seeley District) The area around the junction of Halladay and Three-Mile-Bridge Roads is important to Middlebury's story. It is here that Col. John Chipman cleared the first land in Middlebury in 1766, that Benjamin Smalley built the first house in 1772 (commemorated by a marker on the south side of Three-Mile-Bridge Road), and that Gamaliel Painter developed his farm (on the continuation of Halladay Road). After his return in 1784 Chipman built a two-story brick house, which was subsequently purchased by William Y. Ripley and burned in 1829. In 1830 — 31 Ripley built the two-story frame house west of the Halladay Road intersection, using the Chipman bricks for his cellar and chimneys. His daughter, Julia Ripley Dorr, made the neighborhood the setting for her novel Farmingdale, and the area received the name as a result. Today it is also known as the Seeley District for the eight generations of Seeleys who have lived in the house and the neighborhood since the mid-19th century.
Across Three-Mile-Bridge Road is the one-story house where John Chipman reputedly lived before building his brick home (which would make it one of the oldest, if not the oldest, extant house in town).
On the north side of Three-Mile-Bridge Road is the burial ground for this district. Here can be found the graves of John Chipman, Goodriches, Smalleys, Seeleys, and other old families who developed this portion of town.
Foote Street (The street name is spelled with the final "e" used by some of the family, though not apparently by old Daniel.) Turn north off Route 7 at the former District 3 Schoolhouse (1835) or south off Quarry Road. This is the area settled by Daniel Foot and his sons, married daughter, grandchildren, and in-laws. The pre-Revolutionary Foot buildings were destroyed, but furnishings buried in the woods survived until the family's return in 1783. At that time Daniel built a small one-story house on the southeast corner of lot no. 6, in which he resided during the years that he developed his farm and his milling interests near the falls. In 1786 the first town meeting was held there. Quite possibly the house still stands (with additions) and can be identified with the southernmost old house on the west side of the road, a modest structure with unevenly spaced windows and set up on a rise. Just to the north of this stands the large house which Daniel built in 1793. It is a two-story structure with unevenly spaced, small paned windows and a central chimney, oriented southward to face the original road which ran from the Foot farm to the falls area. Later Foots added the Greek Revival doorway and attic light. Old foundations behind the house suggest that there was once a further wing to the west. To the southwest of the house was the Foots' barn, where were held the first religious services in town.
Many of the older homes along Foote Street, Schoolhouse Road, and the adjacent stretch of Route 7 were built for the Foots in the late 18th and early 19th century (and then altered or added to by later owners.)
Just to the north of the Daniel Foot house is the area where Foot hoped to have the church built and the town center developed. Further north is the Foote Street burial ground, where the graves of many of the original families in the area can be found as well as the elaborate later monument of Middlebury architect Clinton Smith, whose birthplace is the southernmost house on the east side of the street.

East Middlebury
Located along the Middlebury River on the first level land west of Middlebury Gap (the route taken by the Center Turnpike), East Middlebury was a natural location for the development of a sub-center within the town. In 1790 Jonathan Foot built a sawmill here. By 1812 there were also a general store, an inn, and a branch of the Vermont Glass Factory (producers of "Dunmore Glass"). By 1821 there were several more shops and ten dwelling houses; by 1850 there were fifty dwellings in the self-sufficient village. Of particular interest are:
St. Stephen's Rectory Perhaps built by Jonathan Foot near his mill and thus the oldest house in the village.
The Waybury Inn Built in 1810 by Jonathan Foot as a "place of entertainment." Long known as the "Glen House," it was the first resting place for westbound travelers coming down from the mountains and the last place for those eastbound to fortify themselves before the arduous journey through the gap.
Methodist Church Built about 1830.

Bibliography
The information contained in this booklet has been gleaned from many sources and through the efforts of many people. For the reader interested in pursuing a particular aspect of the history of the town or its buildings, the collections of Special Collections in the Main Library at Middlebury College and the Stewart-Swift Research Center at the Henry Sheldon Museum are highly recommended. For a more complete coverage of Middlebury's history in general, the following are recommended:
Stephen A. Freeman, The Congregational Church of Middlebury, Vermont, 1790-1990: A Bicentennial History, Middlebury Congregational Church, 1990 (a thorough history of the church through 1990).
W. Storrs Lee, Father Went to College, New York, Hastings House, 1936 (a history of Middlebury College from its founding through the Depression).
W. Storrs Lee, Father Went to College, New York, Hastings House, 1936 (a history of Middlebury College from its founding through the Depression).
W. Storrs Lee, Stagecoach North, New York, Hastings House, 1941 (life in early Middlebury).
W. Storrs Lee, Town Father, New York, Hastings House, 1952 (the biography of Gamaliel Painter).
David Stameshkin, The Town's College: Middlebury College, 1800 – 1915, Middlebury College Press, 1985 (a detailed history of Middlebury College from its founding to 1915).
Samuel Swift, History of the Town of Middlebury, Middlebury, 1859 and Rutland, Tuttle, 1971 (one of the early town fathers drawing upon his personal experience and those of his contemporaries to write a very detailed account of Middlebury's first ninety years).
Vermont Division for Historic Preservation, The Historic Architecture of Addison County, Curtis B. Johnson, ed., Montpelier, Vermont Division for Historic Preservation, 1992 (exhaustive listing of virtually every historically significant building in Addison County as well as an historical introduction for the county and each of its towns).

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