15 Best Things to Do in Milton (MA)

A wealthy suburban town to the south of Boston, Milton takes pride in its leafy streets, rich history and parcels of protected open space.

The largest of these is the Blue Hills Reservation, where a chain of granite hills culminates with the 635-acre Great Blue Hill, the summit of which has views of the whole Boston area, and a weather observatory dating back almost 140 years.

We’ll talk about the many things you can get up to in the Blue Hills, as well as the collection of historic properties awaiting your visit in Milton.

For a bit of trivia, this town is the birthplace of U.S. President George H. W. Bush, and the famous architect Buckminster Fuller.

1. Blue Hills Reservation

A large chunk of southern Milton is taken up by the Blue Hills Reservation, encompassing the range of the same name. This state park is on 7,000 acres, with more than 125 miles of trails and innumerable sites of interest.

Great Blue Hill, the tallest of the 22 peaks in the range, stands at 635 feet and is within Milton’s boundaries.

The same goes for a host of other attractions and amenities, like the reservations’s headquarters, the Blue Hills Trailside Museum, Houghton’s Pond and the hilltop Blue Hill Observatory, which we’ll describe in more detail below.

For the truly intrepid, the rollercoaster Blue Hills Skyline Trail leads you across the range’s ridge for 15 miles, with views of the entire Boston metropolitan area and Harbor Islands to keep you going.

2. Eustis Estate Museum

On the edge of the Blue Hills you can visit this sumptuous late 19th-century house in a beautiful 80-acre landscape. Built in 1878 for William Ellery Channing Eustis, whose family had a long history in the area, the estate’s Eclectic mansion was designed by noted architect, William Ralph Emerson (1833-1917).

This stone building is loaded with original architectural details and design elements, to a degree that distinguishes it from many historic residences in the Boston area.

The property, guarded by a quaint gatehouse, was acquired by Historic New England in 2012 and can be admired on guided or self-guided tours.

The organization has three galleries here, show off its large collections of artwork, artifacts, photography and ephemera with temporary exhibitions.

3. Blue Hills Trailside Museum

This museum, run by Massachusetts Audubon Society, has been open to the public since 1959.

The Blue Hills Trailside Museum is the primary interpretive center for the Blue Hills Reservation, combining natural history exhibits with several enclosures for native wildlife.

Children in particular will appreciate these exhibits, keeping animals like red foxes, a river otter and various birds of prey that have been rescued and are unable to survive in the wild.

The museum offers all kinds of seasonal programs, for anything from bird-watching basics to the science behind monarch butterflies’ 3,000-mile migration to Mexico each fall.

4. Blue Hill Observatory Science Center

Many of the first scientific measurements of upper atmosphere weather conditions were made at this observatory, founded atop Great Blue Hill in 1885.

The meteorologist Abbott Lawrence Rotch (1861-1912) chose this location as it’s the highest point within ten miles of the Atlantic Ocean on the East Coast south of central Maine.

As the longest continuously operating weather observatory in the country, the facility is still active, and still adding to its enormous 130+ year database of scientific observations.

On a guided tour you can learn more about climate, discover the observatory’s vital contributions to meteorology and peruse weather instruments going back three centuries.

5. Forbes House Museum

Dating to 1833, this handsome Greek Revival residence was built atop Milton Hill for the widow Mrs. Margaret Perkins Forbes, who lived here with her four daughters.

The land had previously belonged to the last royal governor of Massachusetts, who we’ll talk about a bit later.

As well as enjoying stunning views, the Forbes House had rare innovations including indoor plumbing and central hearing, and would remain in the family for four generations up to 1962. The interior is still filled with Forbes family possessions.

These are nothing short of captivating, and include numerous works of art, silk, furniture and ceramics imported from China, Lincoln and Civil War pieces, and artifacts from Captain. Robert Bennet Forbes’ humanitarian mission to Ireland in 1847.

6. Houghton’s Pond

Come summer, a go-to in the Blue Hills Reservation is this picturesque spring-fed kettle hole pond, created by retreating glaciers at the end of the last Ice Age.

On the northern shore of Houghton’s Pond there’s a sandy beach with a roped swimming area, all complemented by showers, restrooms and picnic areas.

Generally, lifeguards are on duty from Memorial Day weekend until Labor Day. There’s also a children’s playground and an assortment of sports facilities close by, and you could park here if you want to access the trails that snake off into the wooded hills from the eastern end.

7. Turner’s Pond

A treasured piece of nature in the heart of Milton, Turner’s Pond is just behind Glover Elementary School and lies within a 26-acre park.

The pond dates to the 1880s, when Milton Ice Company founder Jacob A. Turner dammed Aunt Sarah’s Brook, and the resulting ice pond produced around 4,500 tons of ice each year at its peak.

Later, Turner’s son, Roger F. Turner (1901-1993) learned to skate here and went on to enjoy a long stint as reigning U.S. Figure Skating Champion from 1928 to 1934.

A haven for waterfowl, songbirds, turtles and frogs, the pond is ringed by a perimeter path and is a local fishing spot.

8. Milton Centre Historic District

On a short stretch of Canton Ave, just west of Reedsdale Rd you can visit Milton’s historic civic heart.

Laid out on Academy Hill, this was the site of Milton’s third meetinghouse, built in 1727, replaced in 1788 by the First Parish Church, which is now the district’s oldest surviving building.

There are 11 historically significant buildings on these 11 acres, including the modest-looking Powder House, built in 1811 in preparation for hostilities with the British.

Also look out for the Chemical Engine House (1881), the Central Firehouse (1888) and the Beaux-Arts-style Milton Public Library from 1902.

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

9. Governor Hutchinson’s Field

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

From 1734 this was part of the country estate of Loyalist politician Thomas Hutchinson (1711-1780), the 12th Governor of the Province of Massachusetts Bay.

In Hutchinson’s time there was an orchard here, and this had been cleared by the 19th century. Now the open field gives you far-reaching vistas, over the Boston Harbor Islands, the Boston Skyline and the extensive salt marshes on the Neponset River in the foreground.

10. Mary M.B. Wakefield Estate & Arboretum

On the west side of Brush Hill Rd in Milton is an historic estate that was owned by the Davenport family for more than 300 years before being taken over by a charitable trust in 2004.

The Wakefield Estate’s last resident was Mary May (Polly) Binney Wakefield (1914-2004), who inherited the property in 1952, and was a distinguished gardener and landscape architect, active in regional garden clubs and organizations.

Today you can take a self-guided tour around the 22 acres of formal gardens, woodlands, orchards and wetlands that she nurtured. The annual high point is Dogwood Days in June, when more than 300 kousa dogwood trees are in flower.

11. Quincy Quarries Reservation

Close to Milton, on the edge of the Blue Hills Reservation, is the site of the first large-scale granite quarry in the United States.

A 22-acre section of the vast Quincy Quarries is preserved as a public recreation area by the DCR, while another large chunk has been relandscaped for the semi-private Granite Links golf course to the west.

The quarries were worked from 1825 to 1963, and provided the stone for Charlestown’s Bunker Hill Monument (1843).

After being abandoned, these pits soon flooded, becoming a public safety hazard, before largely being drained and officially opened to the public in the mid-1980s.

The great walls of rock are coated with colorful graffiti and have long been popular with rock climbers. This is yet another awesome vantage point for Boston and the South Shore, and a magical place to watch the sun go down.

12. Granite Railway

Anyone with an interest in the history of engineering will be enthralled by the site of one of the first railroads in the United States.

On the north side of the Quincy Quarries Reservation is the preserved inclined plane, designed by construction engineer Gridley Bryant (1789-1867) to transport that stone.

The Granite Railway was begun in April 1826, and was in operation by October of that year, which is quite a feat considering that almost every element of the railroad, from cars to switches, had to be designed from scratch as it was all new technology.

The incline at Granite Rail Ct is accompanied by a kiosk and information panels, and was placed on the National Register of Historic Places in 1973.

13. Suffolk Resolves House

At 1370 Canton Ave is the historic house where, on September 4, 1774, the Suffolk Resolves were signed.

A step towards the eventual Declaration of Independence, this declaration reflected the escalating colonial animosity of the period.

The document announced a boycott of goods imported from Britain unless the punitive laws passed by Parliament in 1774 (the Intolerable Acts), in response to the Boston Tea Party, were repealed.

Following a dendrochronological survey, the oldest portion of Suffolk Resolves House has been dated to the 1760s, and the building was moved to its current location in 1950 to preserve it from demolition.

Today the Milton Historical Society welcomes the public for monthly open houses, with details published on the society’s website.

14. Cunningham Park

When Forbes family member Mary A. Cunningham, (born Mary Abbott Forbes) passed away in 1904 she left her large fortune to a trust to benefit the people of Milton.

Within months the trustees had purchased this 100+ acre plot and in 1905 opened Cunningham Park as a public space for Milton’s residence.

Still owned and managed by a private foundation, Cunningham Park surrounds a large swimming area, almost an acre in size and known as “The Pond”.

This is open from mid-June to mid-August and offers swimming lessons for children. Among the other amenities are multipurpose fields, baseball diamonds (regulation and little league size), tennis courts and playground equipment.

15. Blue Hills Ski Area

Another of the many things you can do in the Blue Hills Reservation is downhill skiing and snowboarding, at this ski area a few minutes away in Canton.

With a vertical difference of more than 300 feet this small-ish mountain has a skiable area of 60 acres.

The eight runs are mostly geared towards beginners, and since it opened in 1950 the Blue Hills Ski Area has been a fine introduction to skiing for generations of local families.

Snowmaking capacity has more than doubled recently, so there’s a long season here, and if you need rentals, Blue Hills has packages for all ages and sizes.