The house was the location of the first town meeting in 1759 when Princeton was a district (not a town), and served for while as a tavern. Later owned by Thomas Hastings Russell and known as Locust Lawn, it was converted to a summer residence in the early 1890s with an elaborate porch.

This Georgian Cape with a large ell is located on Rt. 62 - Hubbardston Road near Goodnow Road, just west of the town center. It was built in two parts – the first in ca.
1757, with the other part moved to the site in 1790.

Now owned by the state (DCR), this was part of an early farm, and in the 20th century was converted from a farm building into a dwelling by Frank (Matches) Macys. It was sold to Olive Gates in 1939 and deeded to Wachusett State Reservation in 1969. It is now vacant.

In 1884, Edward D. Goodnow gave the town the land and this building, which became the library and school for some time. The Romanesque granite and brownstone building had been built in the previous year (1883), designed by Earle, the same architect for the Town Hall, and constructed by Norcross Bros. of Worcester.  It commands an excellent view.

This Federal style house built for Captain Harrington was enlarged and run as an inn for Harvard professors and later for working women (1890). It continued in operation until 1989, and now is owned by McLean Hospital.

This Greek Revival building, once the East Princeton Schoolhouse #3, was used by a mechanics group.  It has not been used as a school since 1949.  It has been vacant since the 1960s, though with some meetings continuing there into the 1980s. The East Princeton Improvement Society also used to meet here. There is only limited parking, which is restricted, and the hall is located on a busy road.

Built by Ward Nicholas Boylston on the former Moses Gill Farm. Asher Benjamin, the author of The Practical House Carpenter, and an architect in Charles Bulfinch’s firm, oversaw construction of the house. Changes were made in 1853 in time for the marriage of one of Boylston’s daughters. Four generations of Boylstons lived here until 1918. Also known as Homeward Bound. The Boylston farm had large barns, prize Jersey cows and 550 acres of land.

The Bentley Trust Land, so named for the recent ownership of the land, lies in the western part of Princeton along the northwestern end of Gates Road and the eastern end of Old Colony Road. The large property includes over 168 acres of land with 6,000 linear feet of frontage along these roads.

East Princeton Village was a small manufacturing center from the second quarter of the 19th century into the early 20th century. The fast moving Keyes Brook, which flowed from Paradise Pond in northern Princeton, provided waterpower for early chair manufacturing.

The Olive Gates House is one of two houses on Wachusett Mountain that are owned by the Department of Conservation and Recreation. This house, located on Westminster Road on a property named South Druim, is part of a farm that dated back to the late 18th and early 19th century when it was owned by Aaron Perry, followed by Nathan Perry and John P. Rice (1830). In the early 1900s after the house burned, Frank Macys purchased the farm buildings and converted one to a dwelling. In 1939 Olive Gates purchased the property and owned it until 1969, when the 211-acre South Druimwas given by Gates’ will to the Mount Wachusett Reservation in memory of William H. and Alicia F. Gates.

The Superintendent’s House is the other house on Wachusett Mountain that is owned by the Department of Conservation and Recreation. It was built in 1903 for Guy Chase, the first park superintendent, on Echo Lake Road at Mountain Road, near the base of the mountain, and served as Park Headquarters.  The 18 acre parcel was purchased in 1901 from Frederick E. Reed for the Wachusett State Reservation.

Hall’s Field is located on the south side of Gregory Hill Road, which leads down the hill from Princeton Center towards East Princeton. The hillside east of Princeton Center includes farmsteads with dwellings, barns, wooded land, and acres of meadows with stonewalls and a stream at the bottom of the hill. The twenty acres of rolling fields along the south side of Gregory Hill Road is called Hall’s Field, named for the family that has preserved this landscape.

Listed in the National Register as part of the East Princeton Village Historic District, Mechanics Hall is one of Princeton’s most important, yet under-utilized, civic buildings, and is an anchor of this historic district. Mechanics Hall is the best if not the only example of a Greek Revival municipal structure in Princeton.

Hubbardston Road (Route 62) leads from Princeton Center westerly to Hubbardston. The Smith Farm comprises land on both sides of Hubbardston Road about a mile from the Center and east of the Wachusett Wildlife Sanctuary. Extensive rolling hayfields and meadows, hedgerows, the farmstead cluster, and an early 20th century swimming pool form the scenic vista of Smith Farm. This former dairy farm operated by the same family for generations includes over 250 acres.

The Town Pound was constructed in 1768 just north of the Meetinghouse Cemetery on Mountain Road. This was the first town center – the location of the first meetinghouse (1764) and cemetery (1765). The first piece of land, which was a five-acre hilltop site, was given by John and Caleb Mirick[??] in 1759 for a public meetinghouse and a training field; this was followed by Moses Gill’s gift of 20 acres on the west side of Mountain Road for a burial ground and common land. The Town Pound was constructed as a 30-foot square with walls that were six feet high.

Wachusett Mountain is the highest point in eastern Massachusetts, rising to 2,006 feet above sea level. The mountain includes approximately 10,000 acres, using the 1,000 feet above sea level mark as the base: This is equivalent to about 1/3 of the land area of Princeton.  Part of the mountain is also in Westminster and part in Hubbardston. The Wachusett Mountain State Reservation comprises 1,350 acres of land, with trails, roads, a ski lodge (partially in Westminster) and other natural and man-made features of note. Natural features include an old growth forest, Balance Rock and other glacial boulders along Westminster Road.