Captain Wyman raised a company of 24 Ashby men to help fulfill the Provincial Congress resolution to raise 13,000 troops. His company was in Col. Prescott's regiment at the Battle of Bunker Hill, returning in October, 1775.

The Center was established with the building of the first meetinghouse and burial ground. Early settlers traveled along roads that followed Native American trails: County Road to Main Street was an east-west route to Watatic Pond.

The Stock Farm’s 230 acres of hayfield, pastures and forest front on the north side of Main Street west of the town center. The largest extant farm in Ashby, known for a short period as Middlesex Stock Farm, it has a history of raising livestock that have been sold nationally and regionally for many years. The present tenant, the Morgan Horse Organization, raises Morgan horses to be trained for dressage. Also on the farm are the headwaters of Trapfall Brook that flows into Willard Brook. A religious memorial statue sits on top of Caton Hill that rises at the northern edge of the property.

Often referred to as the Old Burial Ground, this cemetery was established on the Common in 1767 at the time of the incorporation of the town. Less than two acres, the burial ground is behind the First Parish Church and bordered by the New Ipswich Road on the east side where the brick receiving tomb is located. The church, its parking area and carriage sheds form the southern edge. A dry laid-stone wall borders the west side. Slate headstones show distinctive 18th century motifs, but the cemetery also includes later marble and granite markers. The northwest corner holds the marker for Prince Estabrook, African American patriot wounded at the Battle of Lexington. Originally he was buried outside the burial ground, but was recently reinterred inside the cemetery walls.

The newest of the Ashby cemeteries, Glenwood was established in 1867 just after the Civil War. It is a twelve-acre trapezoid set back from the roads and framed by mature trees on three sides. Entrance is on the north side via a long driveway from Main Street marked by cruciform shaped granite piers, with no gate. To the right of and in front of the entrance piers is a large meadow that belongs to the cemetery but is not yet in use. A narrow tributary of Trapfall Brook flows along the northwest tip of the property.

A narrow two-acre lot fronting on West Road, this cemetery is an old family burial ground that was started during the Revolutionary War. In the early 20th century, the many Finnish families who settled in the western part of Ashby used the cemetery. Its entrance is an opening in the middle of the white board fence that lines the road. The ground is covered with moss, grass and wildflowers.

Local lore has identified stone outcroppings as Indian Caves in the woods near West Road. Part of the town’s oral tradition about its Native American Heritage, the large slabs of rock form overhangs that might have been used as shelters. It has also been reported that some artifacts have been found in the vicinity of these naturally occurring caves. Residents have expressed an interest in establishing whether the local stories have any basis in fact.

Located just north of the outlet of Ashby Reservoir is a small mill village known as South Village. Here Ephraim Hayward established a gristmill in 1800. At the outlet of the reservoir where the water spills into Willard Brook are the two mill buildings and some mill housing. The mill complex is owned by the Middlesex County Foundation and is operated as Camp Middlesex, a 4-H camp providing recreational and educational uses. The site is unique because so much of the two early mills, saw and grist, is preserved, along with the gear system. The water falls from the spillway between the two mills, the gristmill on the west side, the sawmill on the east side. The mills are connected by a walkway over the brook. The last in a long series of mill operators, William O. Loveland, operated the mills until the 1920s and provided the electric lighting for the town up to that time. The Middlesex County Foundation has owned and respectfully maintained the property since ca. 1941.

This two-lane road winds through Willard Brook State Park nearly parallel to Willard Brook and is known as the Townsend Road. Although a numbered road, Route 119 is scenic and colorful. Where it is part of the state forest, there are scenes of the brook, waterfalls, campgrounds and forested areas with rock outcroppings. Wooded areas slope down to the road that climbs to Ashby Common. Along the road in the village of Ashby are many historic houses, the town library, the Common itself, the First Parish Church and a large Colonial revival town hall (former school) which is on Main Street in Ashby center. After passing through the center the road opens to pastoral views across meadows and tilled fields before it descends to cross Watatic Pond and continue into Ashburnham. As a numbered road, it is ineligible for designation as a Scenic Road under the current law – yet it is a major defining feature of the town that needs sensitive treatment and protection of its historic fabric.

In 1978, plans to reconstruct Route 31 led to local determination to save the bridge and reroute the highway slightly to cross Trapfall Brook via a modern bridge. The Trapfall Stone Arch Bridge is a granite block bridge arching over the brook. Now a walking trail, the old road crosses the bridge and drops off to the brook where the full structure of the bridge is visible with each 1860 granite block still in place.