When the town of Woodstock was created on January 1, 1851, Council was immediately petitioned by residents to build a Market House. Two years later, the Town purchased the Rising Sun Tavern property from Daniel Phelan for a Town Square. A competition was held to design a Market House and Town Hall. Antoine Grobl submitted the winning designs. The Town Hall was Woodstock's first municipal building. Over the years it has served as the Town's first market, first public assembly hall, first fire hall, first police lock-up, first permanent meeting place of Council and first offices for mayor and staff.

The Woodstock Market was built in 1895 by architect W.B. Ford, using 140,000 feet of lumber and 1 1/4 miles of putty, on a site previously occupied by wooden market sheds. The low roof and wide canopies were typical of market construction in this period, and interesting features include the twin towers, the drinking fountain at the front door, and the use of stone in the trim. Quarters for the town police were incorporated in the original plans. Eventually police headquarters were moved to a new building, and the Saturday market relocated. The building was renovated in the 1990s, and as of 2003 houses Theatre Woodstock in one end of the building, and a restaurant in the other end.

The current City Hall building was originally built in 1901 as a post office during the term of Alexander McClenaghan, postmaster for 30 years. Borgue Des Rivieres of Ottawa were the architects and William Hall Burns, a prominent Ottawa artist and sculptor of the Library of Parliament, was commissioned to do the exterior stone carving. Built of warm sandstone, with decorative trim in the gables and a bold corner tower with four clocks, it was converted to municipal offices in 1968.

(Woodstock Museum National Historic Site)
The Woodstock Public Library was built in 1909 by Chadwick and Beckett of Toronto on a Carnegie grant, and is considered on of the most attractive Carnegie libraries in Ontario. It is in the classical revival style, with bi-chromatic brickwork, well balanced windows and a beautifully proportioned and dramatic rotunda. The library traces its history back to a reading society formed in 1835 with Rev. William Bettridge of Old St. Paul's Church as president, and possesses the only complete set of minute books in the province dating back to 1835. The library was renovated and expanded in 1996.

The old armouries were erected in 1904 by Nagle and Mills of Ingersoll as the home of the Oxford Rifles. The crenellated towers give an appearance of heavy fortifications, and the architecture reveals function through exterior form, making interesting use of stone and brick. In 1971, after being declared surplus by the Department of National Defence, it was transformed into offices for the Oxford County Board of Education, at which time its two wrought-iron spiral staircases (valued at $3000 each) were sold at a public auction for $250 each. As of 2003 it is occupied by BDO Dunwoody ant the Woodstock Trinity Private School.

The jail was built in 1845 by Hamiltion architects Clark and Murray in the Italianate style, with many arches and an octagonal 2 1/2-storey tower; in this case, the architecture camouflages the function. Four men and one woman were hanged in the yard, including the infamous Reginald Birchall who was convicted of murdering his gentleman farmer apprentice. This was Victorian Canada's most sensational murder case. The death mask at the entrance is of blind Thomas Cook, hanged in 1862 for murdering his wife. Public hangings were eventually discontinued. This building was restored with spectacular results by C.A. Ventin, an architectural firm from Simcoe, after a decade of lobbying by the Save the Jail committee. As of 2003, it is occupied by the Oxford County Board of Health.

Built in 1892 to replace a Regency predecessor of 1839, the Court House is a massive building of sandstone in the Richardsonian Romanesque style with a complex roofline. The first architect was dismissed in 1890 after the walls were found to be faulty, and replaced by Cuthbertson of Woodstock and Fowler of Toronto. Monkey heads are hidden among the capitals of the red marble pillars at the front two entrances, and the monkey at the peak is said to have been carved by the contractor to represent the county council after a dispute over payment.

The old registry office was constructed in 1876 to replace an earlier building on the County Square's opposite front corner. It served as a registry office until 1952. Italianate in style like the old jail, it is highlighted by semi-circular masonry over the windows. This feature is carried on in the arch over the door. Its walls are two feet thick and its roof is said to be filled with sand, making the structure fireproof and conforming to the design plans common to registry offices of that era in Ontario.

Central Public School was built in 1880 as an eight-room schoolhouse for 245 pupil; in 1923 the north bell tower was razed and another and another eight rooms were added, then the gymnasium was built in 1949. There are two impressive identical entrances, decorative brickwork separating the first and second floors, and decorative gables on a steeply pitched roof. Until 1907 Central served as a model school for the training of teachers and principals. The building underwent major renovations in 2001, and as of 2003 is still in use as a public school.

The Perry Street Fire Hall was built in 1899 to house two horse-drawn fire carts at a cost of $7500. The fire hall features a square tower with detailed brickwork at the top, and a miniature tower to the right. The tower bell used to ring for fires, curfews and lost children, and is now mounted outside City Hall. On Saturday evenings, citizens would gather to watch the horses rush out of their stalls at the sound of the regular 9 o'clock bell, race around the building and back them selves into the shafts ready to be harnessed to the fire cart. The fire hall has been converted to office and retail space.