15 Best Things to Do in Watertown (MA)

Washington Tower, Watertown

Founded in 1630, Watertown was one of the earliest Massachusetts Bay Colony settlements, and came about after a group of Puritan immigrants traveled up the Charles River. In the early 1830s, the hilly easternmost part of Watertown was chosen for Mount Auburn Cemetery, a new and massively influential kind of burial ground, in a picturesque …

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15 Best Things to Do in Chelmsford (MA)

Chelmsford Center for the Arts

In the Merrimack Valley, Chelmsford is a likable town crossed by Interstate 495, Boston’s outer beltway. Chelmsford was incorporated as long ago as 1655, and right on the Town Common is a cemetery founded that very year. The common is still integral to life in Chelmsford, hosting almost every important public event on the calendar, …

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15 Best Things to Do in Randolph (MA)

Horseback Riding

This suburban city is on the South Shore, at the foot of the Blue Hills, which pass by to the north. Randolph is great if you love the outdoors, with many of the most cherished spaces in the Blue Hills Reservation state park close by, like Ponkapoag Pond, renowned for its Atlantic white cedar bog. …

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15 Best Things to Do in Dartmouth (MA)

Round Hill Town Beach

One of the largest towns by area in Massachusetts, Dartmouth is on the state’s South Coast and sits next door to the famous old whaling port, New Bedford. Sparsely populated, Dartmouth comprises a series of historic villages, set amid farmland, vineyards, marshlands and woods. In the south, on Buzzards Bay, the town has a maritime …

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15 Best Things to Do in Franklin (MA)

Mountain Biking

This small city in Norfolk County has a history going back to 1660, but took an important step after incorporation in 1778 by becoming the first place in the country to be named after Benjamin Franklin. Not long after, the Founding Father sent the town a collection of books, which is the origin of the …

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15 Best Things to Do in Holyoke (MA)

Ashley Reservoir

An early planned industrial community that produced paper, silk and alpaca wool, Holyoke was laid out in the 1840s, and is a rare New England city to have a grid plan. Something special about the industrial cityscape is a network of power canals. In the 1880s this system gave rise to innovations in the field …

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15 Best Things to Do in Andover (MA)

Downtown Andover

This well-heeled town in northeastern Massachusetts was incorporated as long ago as 1646, and has the highest point in Essex County, with views of the Boston skyline, 20 miles away. Andover is known for the ultra-prestigious secondary school Phillips Academy, founded in 1778 and with Humphrey Bogart, George H. W. Bush, George W. Bush, Jack …

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15 Best Things to Do in Natick (MA)

South Natick Dam Park

Near the heart of the MetroWest region, 10 miles west of Boston, Natick was settled in the mid-17th century by the Puritan missionary, John Eliot (1604-1690). Natick was one of a network of “praying towns” inhabited by converted indigenous Americans, and for decades the church here was led by a Native American pastor, Daniel Takawambait …

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15 Best Things to Do in Braintree (MA)

Pond Meadow Park

Chartered as long ago as 1640, Braintree is a South Shore town that once included Quincy in its boundaries. That means some pivotal figures in the early history of the United States were born within Braintree’s original limits, among them John Adams, John Quincy Adams and John Hancock. Another important person born in Braintree was …

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15 Best Things to Do in Shrewsbury (MA)

Broken Creek Vineyard and Winery

Separated from Worcester by Lake Quinsigamond, Shrewsbury is a city of almost 40,000, noted for its large Asian American population. The city was incorporated as long ago as 1727, the same year its most famous son, General Artemas Ward, was born. In summer you can visit Ward’s home, now a museum owned by Harvard University. …

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