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Thomas and Esther Smith House is a historic house at 251 North West Street in Agawam, Massachusetts. It is one of the oldest houses in Agawam. The house is situated on 1 acre (0.40 ha) of land about 5 miles (8.0 km) west of the Connecticut River, at the foot of Provin Mountain. It is a vernacular 1+1⁄2-story house with plain Georgian styling. The main block of the house is three bays wide, with a gambrel roof and a central chimney. A 1+1⁄2-story addition on the western side of the house as a gabled roof. The main block's foundation is fieldstone, while that of the addition is brick and concrete block.Inside the house, the main block follows a fairly standard Georgian four-room plan. A vestibule with a dogleg stair separates a hall and a parlor in the front, and the rear is divided asymmetrically into a large kitchen space and a small bedroom. Fireplaces open from the central chimney onto the hall, parlor and kitchen. The kitchen fireplace is particularly deep, and includes a bake oven (now coated with a layer of concrete) at its rear, rather than a more typical placement on the side. The upstairs of the main block is divided into four bedrooms, all with very basic finishing work. The exterior walls and ceilings are plastered, while the interior walls which separate them are either plastered or of simple wood construction.The addition, built c. 1930s, is accessed from the small bedroom space, and includes a kitchen space that dates roughly to the period of its construction. The kitchen is at the level of the main part of the house, but a doorway leads to stairs going up and down to rooms in the rest of the addition, which were laid out to provide a separate living space.The construction date of the house is uncertain, and is believed to have been sometime before 1758, when a deed mentions the home of one George Mixer on this parcel of land. The purchaser of the land, Thomas Smith, was a carpenter and housewright, and may have been this house's builder. Tree ring dating places some of the house's structural elements somewhat later, circa 1790. The house was built using a plank framing method that is distinctive to the Connecticut River valley.The property remained in the Smith family until 1843. It was owned by the Park family until 1910, and then went through a succession of owners before its acquisition by the Agawam Historical Society in 2002. The house remained without modern amenities until the 1950s. It is now operated by the historical society as a house museum. It was listed on the National Register of Historic Places in 2005.

The Hampshire and Hampden Canal was the Massachusetts segment of an 86-mile (138 km) canal that once connected New Haven, Connecticut, to the Connecticut River north of Northampton, Massachusetts. Its Connecticut segment was called the Farmington Canal. The canal dates to 1821 when New Haven businessmen began to raise capital and investigate a possible canal route from their harbor to central Massachusetts, and on to Barnet, Vermont, and Canada beyond. In this original vision, the canal would pass through Farmington, Connecticut, to the border at Southwick, Massachusetts, then join the Connecticut River near Northampton, and from there continue to the St. Lawrence River through Lake Memphremagog and the valley of the St. Francis River. Two side canals were also envisioned: one running from Farmington through Unionville, Connecticut, to Colebrook, Connecticut; the other linking to the Erie Canal via the Hudson River or the proposed (but never built) Boston and Albany Canal. Benjamin Wright, the Erie Canal's chief engineer, was hired to conduct a preliminary survey from New Haven to Southwick, Massachusetts. In 1822 he gave a positive report: "The terrain is favorably formed for a great work of this kind and a canal may be formed for considerable less expense per mile, than the cost of canals now in the making in the state of New York." That same year, the Connecticut legislature granted a charter to the Farmington Canal Company, and on February 4, 1823, Massachusetts granted its corresponding charter to the Hampshire & Hampden Canal Company. After this second charter was granted, work began. Ground-breaking ceremonies took place on July 4, 1825, at the Massachusetts–Connecticut border. However, when Connecticut Governor Oliver Wolcott Jr. employed the ceremonial shovel, it broke in his hands, and this was perhaps emblematic of the canal companies' subsequent fate, as both were substantially under-capitalized and severe financial difficulties plagued their project throughout its existence. Despite these woes, however, construction proceeded with pick and shovel, and by 1828 the canal was open for business from New Haven to Farmington, including its major aqueduct over the Farmington River. By 1835 the complete route to Northampton was finished and operating. When completed, the canal was 86 miles (138 km) long, of which 56 miles (90 km) were in Connecticut and 30 miles (48 km) in Massachusetts. It measured 36 feet (11 m) across on the water's surface, 20 feet (6.1 m) across at the bottom, and 4 feet (1.2 m) deep. Twenty-eight locks were constructed to navigate the 292-foot (89 m) rise in elevation between New Haven and Granby. A further 3.5 miles (5.6 km) of branch canal were constructed to Unionville, later turned into a feeder for the main canal. Financial strains continued, however, and the two canal companies merged to form the New Haven & Northampton Canal Company. A major threat to the canal came in 1838 with the opening of the New Haven Railroad between New Haven and Meriden, Connecticut. Although the canal company took out further loans in the 1840s to improve its efficiency, its stockholders finally petitioned the General Assembly for authority to build a railroad on their canal bed. A charter was granted, and construction commenced in January 1847. The canal closed later that year, and by 1848 trains were running from New Haven to Plainville along the canal's right of way. The company's name remained unchanged, and it kept many of the same investors. It eventually merged with the New York, New Haven and Hartford Railroad in 1887.

Feeding Hills is a section of the city of Agawam with its own ZIP Code (01030) and post office. Line Street in Agawam is generally accepted by residents as being the unofficial border. In the early to mid-19th century, a ditch was dug here to separate the two sections. Feeding Hills contains one quarter of the total population, as well as Provin Mountain, the highest point in the town, and many moderate-sized farms. Today, Feeding Hills is under extensive land development in and around the Provin Mountain communities. Several farms have been split up and sold to developers, resulting in an increased real estate market. Older sections of Feeding Hills, such as those closer to Line Street and Agawam High School, have remained much the same, although in recent years have experienced an exodus of businesses to other parts of town. Feeding Hills contains several churches, shopping centers, and a variety of eateries. It is home to WWLP-TV's transmitting site atop Provin Mountain (their studio has since moved to Chicopee). Agawam's police station can be found on Springfield St., one of the subsection's most populous roads. Of the four elementary schools and three middle/junior/senior high schools, only the junior high school and Granger Elementary are located in Feeding Hills.

Robinson State Park is a state-owned, public recreation area located mostly in the town of Agawam with a small section in Westfield, Massachusetts. The narrow, 1,025-acre (415 ha) state park follows the course of the meandering Westfield River which forms the park's northern border. The park is managed by the Massachusetts Department of Conservation and Recreation.

The Landlord Fowler Tavern is a historic tavern in Westfield, Massachusetts. Probably built in the 1750s, it is a good local example of Georgian architecture despite some unsympathetic modifications, and it was for about a century an important local social gathering point, and a major stop on the east-west stagecoach road. Now divided into apartments, it was listed on the National Register of Historic Places in 1982.

Southwick Regional School (SRS) is a public high school in Southwick, Massachusetts, United States serving grades 7–12 of the Southwick-Tolland-Granville Regional School District, which is made up of the towns of Southwick, Tolland, and Granville.

The Hampden County Training School was a reformatory school for boys at 702 South Westfield Street in Agawam, Massachusetts. Established in 1916, it operated until 1972, providing training agriculture and vocational skills to its charges. In 2010, the state sold the property to a veterans support organization for conversion to residences. The facility opened in 2017. The property was listed on the National Register of Historic Places in 2018.

Agawam Park was an American horse racing track in Agawam, Massachusetts, that was open from 1935 to 1938, when Hampden County, Massachusetts, voted against parimutuel betting.

The Amelia Park facilities are located in Westfield, Massachusetts, United States. The Amelia Park Ice Rink is the only ice rink in Westfield. The main building is a 47,000-square-foot (4,400 m2) facility, a figure skating lounge, three party rooms, a skate rental and sharpening area, four locker rooms and a food concession area. A 65' x 170' outside inline skating rink is located next to the main building. The $6 million facility was created by Albert Ferst in memory of his late wife, Amelia. The facility houses activities and events, such as open skating times, hockey games for Westfield State University, St. Mary's High School, Westfield High School, and Sled Hockey Games. Gardens span 3.1 acres (13,000 m2) and are located across from the main entrance of the arena.

The Mechanic Street Cemetery is a historic early cemetery on Mechanic Street in Westfield, Massachusetts. The 4-acre (1.6 ha) cemetery is the city's oldest, with the oldest documented grave dating to 1683. It was used as a burying ground until the late 19th century, although its use began to decline in the middle of the century, with the advent of the popular rural cemetery movement, which was reflected in Westfield with the establishment of the new Pine Hill Cemetery in 1842. No burials were recorded in the 20th century. Although the cemetery has been subjected to some maintenance work, it continues to suffer the effects of vandalism and weather. The cemetery was listed on the National Register of Historic Places in 2002.

The United States Whip Company Complex or "United States Line Company Complex" is a historic factory located in Westfield, Massachusetts. It was owned and operated by one of the whip-making businesses that led Westfield to become widely known as "Whip City". United States Whip, created in 1892 by the consolidation of several local manufacturers, was the world's largest manufacturer of whips. The factory complex was listed individually on the National Register of Historic Places in 1983, and as part of an expanded Westfield Center Historic District in 2013.

The Westfield Center Historic District is a historic district encompassing 157 acres (64 ha) of the civic, commercial, and industrial heart of Westfield, Massachusetts. It represents a major expansion of the Westfield Center Commercial Historic District, which included only two blocks of buildings along Elm Street in downtown Westfield. The district includes buildings representing the city's growth in the 19th century as a center of the whip-making industry, and its early years as a center for statewide educational institutions, as well as its growth as a regional center of western Hampden County. The commercial district was added to the National Register of Historic Places in 2008; the expansion and renaming of the district took place in 2013.Westfield was settled in the 17th century by English colonists, with its town center forming just west of the confluence of the Westfield and Little Rivers. It was mainly agricultural until the early 19th century, when whip making began as a cottage industry, and the Hampshire and Hampden Canal provided reliable means for moving goods. The town center shifted westward around this time, becoming centered between Park Square and the Westfield River on what is now called Elm Street. The town developed a diverse industrial whose largest component was the whip industry, prompting it to be called "Whip City". That industry would predominate until the advent of the automobile in the 20th century greatly reduced demand. In the late 19th century the city also became home to the state's second normal school, now Westfield State University.The city center is architecturally reflective of much of this history, although buildings from the late 19th and early 20th centuries predominate. Important industrial elements survive, in particular whip factories that include the Sanford Whip Factory, the Westfield Whip Manufacturing Company, the United States Whip Company Complex. The early functions of the normal school are recalled in part by the Westfield Municipal Building (formerly housing that school, and now city hall), and the State Normal Training School, an elementary school built as a training vehicle for teachers in training. Residential neighborhoods developed on either side of the commercial area, portions of which are included in the historic district.