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.
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.
3 Methodist Lane Almost certainly the home of William Young, Middlebury's first cabinetmaker. Built about 1796.
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 (Nichols House) 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.
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.