Top 15 Attractions and Activities in Milton, MA

Located south of Boston, Milton is a prosperous suburban community known for its verdant streets, rich heritage, and well-preserved natural landscapes.

The most extensive of these natural areas is the Blue Hills Reservation, featuring a series of granite hills, culminating at the 635-acre Great Blue Hill, which offers panoramic views of the Boston region along with a historic weather observatory that has been operational for nearly 140 years.

This article will explore the numerous activities available in the Blue Hills and the array of historic sites in Milton.

Notably, this town is recognized as the birthplace of U.S. President George H. W. Bush and the renowned architect Buckminster Fuller.

1. Blue Hills Reservation

A substantial portion of southern Milton is occupied by the Blue Hills Reservation, which covers an area of 7,000 acres and features over 125 miles of trails as well as numerous points of interest.

Great Blue Hill, the highest of the 22 peaks in the region, rises to 635 feet and lies within Milton’s boundaries.

Additionally, the reservation includes various attractions such as its headquarters, the Blue Hills Trailside Museum, Houghton’s Pond, and the hilltop Blue Hill Observatory, which will be elaborated upon further.

For the adventurous, the challenging Blue Hills Skyline Trail traverses the ridge of the range for 15 miles, providing stunning views of the entire Boston metropolitan area and the Harbor Islands.

2. Eustis Estate Museum

Situated at the fringe of the Blue Hills, this exquisite late 19th-century residence is set in a stunning 80-acre landscape. Constructed in 1878 for William Ellery Channing Eustis, a member of a family with deep roots in the community, the estate features an Eclectic mansion designed by the notable architect William Ralph Emerson (1833-1917).

This stone edifice is rich in original architectural details that set it apart from many other historic homes in the Boston area.

Acquired by Historic New England in 2012, visitors can explore the property through guided or self-guided tours.

The organization operates three galleries that showcase its extensive collection of artwork, artifacts, photography, and ephemera through temporary exhibitions.

3. Blue Hills Trailside Museum

This museum, operated by the Massachusetts Audubon Society, has been accessible to the public since 1959.

The Blue Hills Trailside Museum serves as the primary interpretive center for the Blue Hills Reservation, featuring natural history exhibits alongside various enclosures for native wildlife.

Younger visitors will particularly enjoy the displays, which include red foxes, a river otter, and various birds of prey that have been rehabilitated and are now incapable of surviving in the wild.

The museum offers a variety of seasonal programs, ranging from birdwatching fundamentals to the scientific principles behind the 3,000-mile migration of monarch butterflies to Mexico every fall.

4. Blue Hill Observatory Science Center

This observatory, established atop Great Blue Hill in 1885, was the site of some of the earliest scientific measurements of upper atmospheric weather conditions.

Founded by meteorologist Abbott Lawrence Rotch (1861-1912), this location was chosen as it is the highest elevation within ten miles of the Atlantic Ocean on the East Coast south of central Maine.

As the longest continuously operating weather observatory in the United States, the facility remains active and continues to expand its extensive database of scientific observations accumulated over 130 years.

During a guided tour, visitors can learn about climate science, the observatory’s significant contributions to meteorology, and explore weather instruments that date back three centuries.

5. Forbes House Museum

Constructed in 1833, this elegant Greek Revival residence was built on Milton Hill for Mrs. Margaret Perkins Forbes, a widow living with her four daughters.

The property was previously owned by the last royal governor of Massachusetts, whose history will be discussed later.

The Forbes House offers stunning views and features rare innovations such as indoor plumbing and central heating, remaining in the family for four generations until 1962. The interior retains many possessions from the Forbes family.

These artifacts are compelling and include various works of art, silk, furniture, ceramics imported from China, items from Lincoln and the Civil War, and objects associated with Captain Robert Bennet Forbes’ humanitarian mission to Ireland in 1847.

6. Houghton’s Pond

During the summer months, Houghton’s Pond is a favorite in the Blue Hills Reservation, characterized by its picturesque spring-fed kettle hole formed by glacial retreat at the conclusion of the last Ice Age.

The northern shore of Houghton’s Pond features a sandy beach with a designated swimming area, complemented by showers, restrooms, and picnic spots.

Generally, lifeguards are present from Memorial Day weekend until Labor Day. There is also a children’s playground and various sports facilities nearby, along with parking options for those wishing to access the trails leading into the wooded hills from the eastern end.

7. Turner’s Pond

Located behind Glover Elementary School within a 26-acre park, Turner’s Pond is a cherished natural site in the center of Milton.

The pond was established in the 1880s when Jacob A. Turner, founder of the Milton Ice Company, dammed Aunt Sarah’s Brook, creating a pond that produced approximately 4,500 tons of ice annually at its peak.

In later years, Turner’s son, Roger F. Turner (1901-1993), learned to skate on this pond and eventually became the reigning U.S. Figure Skating Champion from 1928 to 1934.

Rich in wildlife, including waterfowl, songbirds, turtles, and frogs, the pond is bordered by a path and serves as a local fishing area.

8. Milton Centre Historic District

Located along a brief stretch of Canton Ave, just west of Reedsdale Rd, you will find Milton’s historic civic core.

Established on Academy Hill, this area was the site of Milton’s third meetinghouse, erected in 1727 and replaced in 1788 by the First Parish Church, which remains the oldest surviving structure in the district.

There are 11 historically significant buildings on these 11 acres, notably including the modest Powder House, constructed in 1811 in anticipation of conflicts with the British.

Also of interest are the Chemical Engine House (1881), the Central Firehouse (1888), and the Beaux-Arts-style Milton Public Library from 1902.

In front of the town hall, the Lira Bandstand hosts Milton’s summer concert series on Wednesdays from early June to mid-August.

9. Governor Hutchinson’s Field

Stretching down towards the Neponset River from Milton Hill is a ten-acre field maintained by the Trustees of Reservations.

Since 1734, this area was part of the countryside estate belonging to Loyalist politician Thomas Hutchinson (1711-1780), the 12th Governor of the Province of Massachusetts Bay.

During Hutchinson’s time, an orchard was located here, but this was cleared by the 19th century. Currently, the open field provides expansive views over the Boston Harbor Islands, the Boston skyline, and the sprawling salt marshes along the Neponset River below.

10. Mary M.B. Wakefield Estate & Arboretum

Located on the west side of Brush Hill Rd in Milton, this historic estate was owned by the Davenport family for over 300 years before being transferred to a charitable trust in 2004.

The last resident of the Wakefield Estate was Mary May (Polly) Binney Wakefield (1914-2004), who inherited the property in 1952 and was an accomplished gardener and landscape architect actively involved in local garden clubs and organizations.

Visitors can now embark on a self-guided tour of the 22 acres comprising formal gardens, woodlands, orchards, and wetlands she cultivated. The annual highlight occurs in June during Dogwood Days, when more than 300 kousa dogwood trees blossom.

11. Quincy Quarries Reservation

Adjacent to Milton, at the boundary of the Blue Hills Reservation, lies the site of the first significant granite quarry in the United States.

A designated 22-acre segment of the expansive Quincy Quarries is preserved as a public recreational area by the Department of Conservation and Recreation (DCR), while another significant portion has been revitalized for the semi-private Granite Links golf course to the west.

The quarries operated from 1825 until 1963, contributing stone for the construction of the Bunker Hill Monument (1843).

After their closure, the flooded pits became a public safety concern, but were largely drained and officially opened to the public in the mid-1980s.

The towering rock walls are adorned with vibrant graffiti, making the site a favored location for rock climbers. It also serves as an excellent vantage point for viewing Boston and the South Shore, particularly during sunset.

12. Granite Railway

History enthusiasts will find the site of one of the first railroads in the United States particularly fascinating.

Located on the northern side of the Quincy Quarries Reservation, the preserved inclined plane was designed by construction engineer Gridley Bryant (1789-1867) to transport granite.

The Granite Railway began operations in April 1826 and was functional by October of the same year, an impressive accomplishment considering that virtually every element of the railway, including cars and switches, had to be innovatively designed as the technology was unprecedented.

The incline at Granite Rail Ct is accompanied by informational displays and was designated as a historic site on the National Register in 1973.

13. Suffolk Resolves House

Located at 1370 Canton Ave, this historic residence is where the Suffolk Resolves were signed on September 4, 1774.

This declaration marked a step toward the eventual Declaration of Independence, reflecting the growing colonial discontent of the era.

The document called for a boycott of British goods unless the punitive legislation enacted by Parliament in 1774 (the Intolerable Acts)—in response to the Boston Tea Party—was retracted.

Following a dendrochronological assessment, the oldest section of the Suffolk Resolves House has been traced back to the 1760s; the building was relocated to its current site in 1950 to protect it from demolition.

Today, the Milton Historical Society invites the public for monthly open houses, with details available on their website.

14. Cunningham Park

Upon the passing of Mary A. Cunningham, a member of the Forbes family, in 1904, she left her considerable fortune in trust to benefit the residents of Milton.

Within months, the trustees purchased a plot of over 100 acres, officially opening Cunningham Park to the public in 1905.

Still owned and managed by a private foundation, Cunningham Park encompasses a large swimming area, known as “The Pond,” covering nearly an acre.

This area is accessible from mid-June to mid-August and offers swimming lessons for children. Additional amenities include multipurpose fields, baseball diamonds (both regulation and little league sizes), tennis courts, and playground equipment.

15. Blue Hills Ski Area

The Blue Hills Ski Area, located just a few minutes away in Canton, offers opportunities for downhill skiing and snowboarding as part of the various activities available in the Blue Hills Reservation.

With a vertical drop of more than 300 feet, this modestly sized mountain features a skiable area of 60 acres.

The eight runs are primarily designed for beginners, and since its inception in 1950, Blue Hills Ski Area has served as an excellent introduction to skiing for generations of local families.

Recent enhancements have more than doubled the snowmaking capacity, ensuring an extended skiing season, and rental packages are available for all ages and sizes.