The Historical Society owns the knapsack of Colonel Paul Raymond and powder horns and gun used by Major Paul Boynton            

Eden London was a slave who had escaped from his Fitchburg master and fought with Col. Asa Whitcomb's Regiment, Capt. James Company at Bunker Hill. It was not unusual for slaves to fight in lieu of their owners. He was afterwards owned by Daniel Goodridge of Winchendon and his case became famous as the cause of the "Massachusetts Slave Case of 1806-7, Winchendon vs. Hatfield."            

This was the original town center, the site of training field, the oldest burial ground, a common and first meeting house. The statue has been in place since 1947.            

Referred to as Captain’s Farm for Captain Murdock who was a militia captain, this property is a good example of over-lapping heritage landscapes. It is significant for its setting at the crest of a hill on a narrow semi-paved scenic road with stone wall and trees, for the historic house, and for the scenic vista south across the agricultural landscape of hayfields to Wachusett Mountain, which is in Princeton, Massachusetts. The house has been documented with a construction date of 1765; however, the existing dwelling is a gable-front, side-hall entry with a side wing in the Greek Revival style which appears to date from the second quarter of the 19th century. Possibly an older house is within the existing dwelling. No farm buildings remain with this property. A distinctive stonewall with a tree-lined grassy strip forms the edge along the narrow scenic road.

The Richard Day House is a substantial five-bay, two-story center chimney dwelling under a hipped roof. Presently the house is covered with asbestos shingles, and windows and storms have been changed to two-over-two sash. The house is on the north side of Teel Road west of the Old Centre Common and sits on a slight rise above the road. A couple of mature maple trees grow in front of the house. This is Winchendon’s oldest extant building and the only house surviving from the ca. 1752 settlement. The house is named for Winchendon’s first town clerk, Richard Day, who lived here.

The main intersection in Winchendon Village is where Central Street meets Front Street. On the northwest corner are two historic properties that are central to the streetscape and convey a sense of the old village flavor. These two historic buildings, Joseph’s Variety Store (also known as Joseph’s Block) and the Fairbanks House, are adjacent to one another and face Central Street. Joseph’s Block (1880) has served as a courthouse, clubhouse and commercial block with specialty stores. The two-story building has two store fronts at the ground level and mixed use living quarters above reached by a center entrance. The Sidney Fairbanks House was built in ca. 1853 and probably modified in later years to its Second Empire style with mansard roof. It is a three-story dwelling with Italianate details in window consoles, eave brackets and the bracketed wrap porch. A three-story projecting central pavilion has an open porch at the third level under a hipped standing seam, metal roof that hovers over the main house roof.

The Millers River has two branches. The headwaters are in Rindge, New Hampshire and in Ashburnham/Winchendon, Massachusetts. The branches meet at Whitney Pond in Winchendon Village. From here the Millers River flows westerly for about 37 miles into the Connecticut River at  Montague/Turners Falls, Massachusetts. Several of Winchendon’s mill villages are located on the Millers River or the North Branch.

Several farms line Elmwood Road which leads out of Winchendon Village and turns easterly towards Winchendon Springs. The most prominent farm is the Murdock Farm, comprising approximately 300 acres with a main ca. 1830 Greek Revival house, a large New England barn with cupola, several small farmhouses, other dairy barns and out-buildings, agricultural fields and a dairy bar. Due to the high elevation there are scenic views across the haying fields south towards Wachusett Mountain and north towards Mount Monadnock. Once a dairy farm, the cows have been sold; however the owner continues to make ice cream that is sold at the Murdock Farm Dairy Bar. A few small ponies are kept in paddocks next to the Dairy Bar parking lot. The fields are hayed and presently large hay wagons are parked at the edge of some of the fields along Elmwood Road. Farming the land has become less lucrative, thus more difficult to sustain. Keeping the Dairy Bar open is an important goal for the community since it is a local spot enjoyed by many who come for the ice cream and the views.

The Sanborn Mill is located on the North Branch (of the Millers River) about halfway between Winchendon Springs and Winchendon Village. It is north of Whitney Pond and accessed from Glenallen Street. A winding wooded driveway leads from the road down to the mill building located on the river’s edge. The large three-story brick mill with projecting stair tower is situated with its long side parallel to the river. The mill, which is vacant and in disrepair, has a single story wood frame addition and a one and one-half story brick addition, both projecting from the northeast end of the main block. Most windows are shattered or boarded up and some of the brick walls are crumbling. Yet many defining features remain, including the corbelled cornice wrapping around the main block, segmental arched window openings (some retaining the 12/12 sash), and the five story stair tower with pyramidal roof.

Whitney Pond is a man-made pond at the confluence of the Millers River and the Millers River North Branch. The large (110 acres) irregularly shaped pond is north of Route 12 and east of the main downtown area of Winchendon Village. The outflow of the pond runs under the railroad rights-of-way to the Whitney Pond Dam that has a 25-foot drop. There is little development along the banks of the pond, and access is limited to Glenallen Street where the Millers River flows into the pond and behind Central Street on the northwestern side of the pond. Whitney Pond is stocked each spring with 500 trout and is known as a good fishing hole for trout and other warm-water fish. The North Central Pathway, an old railroad right-of-way, runs along the southern side of the pond.