Cross Street station (MBTA)

The Charles Russell House is a historic house at 993 Main Street in Winchester, Massachusetts. The 2+1⁄2-story wood-frame house was built by Charles Russell in 1841, on a site that was one of the first settled in what is now Winchester. The five-bay facade has a center entry that is framed by sidelight and transom windows, and is sheltered by a portico with fluted Ionic columns. The house also has corner pilasters and a high entablature.The house was listed on the National Register of Historic Places in 1989.

The Carr-Jeeves House is a historic house in Winchester, Massachusetts. Built in 1869, it is fine local example of Second Empire architecture. It was listed on the National Register of Historic Places in 1989.

Wildwood Cemetery is a historic cemetery at Palmer and Wildwood Streets in Winchester, Massachusetts. The cemetery was founded in 1851 and added to the National Register of Historic Places in 1989. This cemetery was established using part of the $3000 gift from Colonel William P. Winchester that was donated on condition that the town be named after him. It was one of the first public spaces laid out after Winchester was incorporated, on land just west of the former Middlesex Canal. It is laid out in the rural cemetery fashion popular in the mid-19th century, with winding lanes a country landscaping. The designer was Amasa Farrier of neighboring Stoneham, who used as his inspiration the published works of Andrew Jackson Downing and John Claudius Loudon. Land was purchased in 1851, and was ready for use the following year. Older graves from the small cemetery at the First Congregational Church were transferred here in 1853. As a result, the oldest dated burials are in 1805. The entrance gateway was added as part of a landscape design developed by the Olmsted Brothers in 1937.Notable persons buried in the cemetery include Massachusetts Governor Samuel Walker McCall (1851–1923), Rev. Howard James Chidley (1878–1966), engineer Harold Kilbrith Barrows (1873–1954), linguist Joshua Whatmough (1897–1964), artist Joseph Foxcroft Cole (1837–1892), and artist Dana Pond (1881–1962). Other prominent burials include philanthropist and peace activist Edwin Ginn, local developer David Skilling, and Harrison Parker, owner of a local mill. It is also the burial ground for many members of locally prominent families, including members of the Symmes, Locke, Richardson, and Johnson families.

Horn Pond is a 102-acre (41 ha) water body along the Aberjona River in Woburn, Massachusetts in the United States. The pond is fed by several brooks and flows out via Horn Pond Brook to the Aberjona River and the Mystic Lakes, eventually reaching the Mystic River and the Atlantic Ocean. It was also traversed by the Middlesex Canal from 1802 to 1860. Yellow perch were the most common species recorded at Horn Pond in a 1982 survey, with additional species, including: largemouth bass, pumpkinseed, bluegill, killifish, chain pickerel, golden shiner, carp, white sucker, brook trout, yellow bullhead, brown bullhead and black crappie. Trout (primarily rainbows, but also browns and brookies) have been stocked in the past, with more fish and trout in the fall.

Snug Gables is a historic house built for Thomas Dreier by Frank Chouteau Brown in Winchester, MA. It was built in 1920 and named after Dreier's wife, Blanche "Snug" Drier. Dreier ran the "Thomas Dreier Service" out of a print shop in the basement, which distributed advertising publications and motivational short stories to area business leaders. After Brown completed a project in 1923 to improve the grounds, it was featured in the August 1923 US edition of what was then known as Country Life Magazine. The house was also featured in advertisements for La Touraine coffee in newspapers throughout New England and New York. One of these was titled "Where Thomas Dreier Lives and Works," describing the household's reputation for hospitality. Another version entitled "Mrs. Thomas Dreier Keeps Here 21 Separate Accounts" notes the organization and careful approach of the matriarch, which leads her to serve La Touraine coffee.Dreier wrote "Sunshine on the Business Trail" at Snug Gables, and several of the short stories within describe the house. Short works by Dreier are engraved on bronze plaques around the property. The Dreiers sold Snug Gables in 1933. After several short term tenants, and the Armstrong and Knox families, each of which owned it for more than a decade, it was purchased in 1968 by the noted physician Alexander Leaf. It remained in the Leaf family until shortly after Alexander's death in 2013.Mr. Brown's architectural drawings and photos of the house are on file at Historic New England. Mr. Dreier's records also contain detailed information about the property, and are on file at the University of South Florida. Snug Gables is listed in the Society of Architectural Historians "Buildings of Massachusetts: Metropolitan Boston."

Winchester Highlands station was an MBTA Commuter Rail Lowell Line station located at Cross Street in the northern part of Winchester, Massachusetts. It originally opened in the mid-19th century under the Boston and Lowell Railroad (B&L) as a flag stop called North Winchester. In 1877, a local real estate developer constructed a new station building, which was renamed Winchester Highlands. The B&L became part of the Boston and Maine Railroad (B&M) in 1887. Service to the station gradually decreased in the 20th century, and the depot was replaced by a wooden shelter around 1943. The Massachusetts Bay Transportation Authority (MBTA) began subsidizing service on the line in 1965. Winchester Highlands and two other stations with low ridership were closed by the MBTA in June 1978.

The Benjamin Thompson House (also known as the Count Rumford Birthplace) is a historic house museum and National Historic Landmark at 90 Elm Street, in the North Woburn area of Woburn, Massachusetts. It is significant as the birthplace of scientist and inventor Benjamin Thompson (1753–1814), who became Count Rumford of the Holy Roman Empire as well as Sir Benjamin Thompson of the United Kingdom. His birthplace was designated a National Historic Landmark in 1975 in recognition of Rumford's scientific accomplishments, which notably include the development of the Rumford stove, a fireplace design that was significantly more efficient at retaining heat in the house than older and larger fireplaces.

The Firth–Glengarry Historic District encompasses a residential area of Winchester, Massachusetts consisting of well-preserved high quality houses built mainly between 1880 and 1900. The district lies between Wildwood Street and Wedge Pond, and includes properties on Pine Street, Glengarry Road, Grassmere Avenue, Dix Street, and Wildwood Street; houses on Curtis Street and Curtis Circle, are excluded from the district. Much of the area was laid out by developer William Firth, and many of its houses were designed by Boston architect Robert Coit. The 13.44-acre (5.44 ha) district was listed on the National Register of Historic Places in 1989.Prior to William Firth's consolidation of land ownership southwest of Wedge Pond in the late 19th century, this area of Winchester was sparsely inhabited. The oldest house in the area is an 1843 Greek Revival structure at 3 Wildwood Street. Two houses were built near Wedge Pond in the 1850s and 1860s, of which the Charles Curtis House (1965, 9-11 Grassmere Avenue) is a particularly fine example of Carpenter Gothic; the Bellows House, built in 1854, is also Gothic Revival in character. In the 1880s and early 1890s three Queen Anne/Stick style houses were built, of which the Langley House (1887) at 10 Pine Street is the most elaborate.After Firth had acquired most of the land in the area, he subdivided into ample house lots, and laid out Glengarry Road and Grassmere Avenue. He hired Robert Coit to design houses which are predominantly Colonial Revival and Medieval Revival (Tudor) in character. Coit's designs used shingling to a significant degree, and mixed in features from other popular revival styles. Firth's own house at 37 Dix Street, built in 1937, is, however, a relatively straightforward Colonial Revival design, with a gambrel roof and modillioned cornice, and with gable dormers and a full-width front porch supported by Doric columns.

Winchester High School is a comprehensive 9–12 high school located in Winchester, Massachusetts, United States. Founded in 1850, it moved into its current location in the spring of 1972. Ranked 29th among Massachusetts High Schools, close to 98% of students graduated in 2016, with about 96% of those continuing to higher education.A major three-phase reconstruction and expansion of the school started in 2014 and was completed in September 2017. Most of the school was rebuilt using the original structural frame. After the complete redesign of the interior of the building, approximately 75% of classrooms now have exterior windows and direct day-lighting versus 25% in 1972. The original internal courtyard was enclosed to create the 2-story dining commons and assembly space. Winchester High School remained in use during construction.

The Wedgemere Historic District encompasses the largest single 19th-century residential development of Winchester, Massachusetts. It is one of the town's largest surviving 19th-century residential subdivisions, with a concentration of high-quality residences built between about 1890 and 1920. The district was listed on the National Register of Historic Places in 1989.

The First Church of Woburn, formerly the First Congregational Church in Woburn, is a historic nondenominational Christian church at 322 Main Street in Woburn, Massachusetts. The congregation, established in 1642, is one of the oldest in the United States, and its church building (the sixth for the congregation) is a local landmark. The Italianate-style church was built in 1860, and its 196-foot (60 m) steeple is believed to be the tallest wooden steeple in North America. The church is home to a historic E&GG Hook pipe organ, dating to the time of the church's construction.The church building has been listed on the National Register of Historic Places since 1992. The congregation was originally Puritan, as were all acknowledged churches in Massachusetts at the time, and was later affiliated with the United Church of Christ in the early 20th century until resigning the denomination in the late 1980s. It is now declared nondenominational in the evangelical tradition but did not drop the Congregational designation from its name until 2018.

Woburn station was a railroad station on the Woburn Branch (formerly the Woburn Loop), part of the Massachusetts Bay Transportation Authority's Lowell Line.