11 Historic Massachusetts Towns Worth Spending a Whole Weekend In

Most Historical Towns in Massachusetts

Beyond Boston’s Freedom Trail lies so much more history. Here are 11 small towns in Massachusetts where history stays alive in creaky taverns, working waterfronts, and streets that still look much like they did centuries ago.

Salem

Salem is famous for its witch trials of 1692, but it was also a major trading port where ship captains got rich bringing spices like pepper and cinnamon from the East Indies. The House of Seven Gables, built in 1668 by sailor John Turner, stands proudly as America’s oldest mansion still standing.

The Peabody Essex Museum, which began as a club for sea captains in 1799, now displays an incredible collection of 840,000 pieces of historical and cultural art.

At the Salem Maritime National Historic Site, you can walk down the half-mile Derby Wharf where tall ships once docked, and visit the 1819 Custom House where taxes were collected.

Deerfield

Deerfield takes you back in time with 11 museum houses from 1730-1850. In 1704, the town faced a devastating raid – French and Native American forces killed 50 villagers and took 112 captive. Walking down the mile-long main street, you’ll see beautiful Georgian and Federal-style buildings, including the 1799 Wells-Thorn House.

Deerfield Academy, started in 1797, still teaches students on its historic campus. The Memorial Hall Museum, opened in 1880, holds New England’s oldest collections, including the Stebbins family’s special heart-and-crown chair from 1710.

Watch craftspeople work just like colonists did, cooking on open hearths and making things with 18th-century tools.

New Bedford

New Bedford ruled the whaling world in 1857 with 329 ships hunting whales to light America’s homes.

The Whaling Museum holds the world’s biggest collection of scrimshaw and a half-scale model of the bark Lagoda. Before writing “Moby-Dick,” Herman Melville worked on the whaler Acushnet here in 1841.

The historic district spans 11 blocks of cobblestone streets lined with fancy Greek Revival mansions. Rich whaling merchants like William Rotch Jr. and Edward C. Jones built these impressive homes, showing how profitable the dangerous whaling business was.

Lexington

On April 19, 1775, Lexington’s Battle Green saw the Revolution’s first blood when 77 brave militia faced 700 British troops. Revolutionary leaders John Hancock and Samuel Adams hid at the Hancock-Clarke House the night before. The house still holds items from that time.

Every Patriots’ Day, 150 people dress up to show visitors how the battle looked. Buckman Tavern, where militia waited that morning, hasn’t changed since then – you can even see musket ball holes in its walls.

Lowell

Lowell’s textile mills along the Merrimack River sparked America’s Industrial Revolution. By 1850, these mills employed 40,000 workers and had more cotton spindles than all eleven Southern states combined. Young “mill girls” earned $3.50 weekly in 1840, changing how Americans worked.

Visit restored mill buildings and see the Suffolk Mill’s water-powered turbines in action. The Boott Cotton Mills Museum shows 88 working power looms, letting visitors feel the noisy, intense conditions workers faced every day.

Marblehead

Since 1629, Marblehead has kept its colonial charm with over 200 pre-Revolutionary buildings. Local fishermen became naval heroes under General John Glover during the Revolution. Old Burial Hill, started in 1638, holds Revolutionary heroes’ graves and offers beautiful harbor views.

The grand Jeremiah Lee Mansion, built in 1768 for $10,000 (a fortune back then), shows off fine Georgian architecture. Its original hand-painted wallpaper and period furniture help visitors imagine life in colonial times.

Sturbridge

Old Sturbridge Village brings 1830s New England to life across 200 acres. More than 40 original buildings, moved from all over New England, show how people lived and worked. The collection includes everything from the 1748 Richardson House to the 1832 Town Bank.

Watch blacksmiths work and farmers plow with oxen. The Freeman Farm keeps old-time animal breeds like Devon cattle and Merino sheep, just like farms did in the 1830s.

Gloucester

America’s oldest seaport, started in 1623, has sent fishing boats out for four centuries. Over 10,000 sailors lost their lives at sea. The Cape Ann Museum tells these stories and shows paintings by Winslow Homer, who lived here from 1873-1881.

The 1925 Fisherman’s Memorial lists lost sailors’ names. At State Fish Pier, opened in 1938, boats still bring in 300 million pounds of fish yearly, keeping the town’s fishing tradition alive.

Cambridge

Harvard University has shaped Cambridge since 1636. Massachusetts Hall, built in 1720, housed Revolutionary War troops and still stands as Harvard’s oldest building. George Washington led the Continental Army from Longfellow House during the 1775-76 Boston Siege.

Later, Henry Wadsworth Longfellow wrote “Paul Revere’s Ride” there in 1860. Cambridge Common, where Washington took command on July 3, 1775, displays three captured British cannons.

Plymouth

While Plymouth Rock looks modest, it marks America’s first Puritan settlement.

Plimoth Patuxet Museums shows both Colonial and Native American life in the 1620s, with buildings made using old methods. The Mayflower II, built in 1957 in England, helps visitors understand how 102 Pilgrims lived during their 66-day journey.

Burial Hill, with graves from the 1620s including Governor William Bradford’s, reminds us that half the settlers didn’t survive their first winter.

Concord

The American Revolution began here in 1775 with the “shot heard round the world” at North Bridge. Famous writers also called Concord home – Ralph Waldo Emerson wrote his groundbreaking work “Nature” in 1836, Louisa May Alcott created “Little Women,” and Henry David Thoreau wrote “Walden” in 1854 after living by the famous pond.

The historic battle site, where 400 colonial militia bravely faced 100 British soldiers, is now part of Minuteman National Historical Park. Guides share stories about that fateful April morning along the preserved 5-mile Battle Road.

Thoreau’s beloved Walden Pond, where he lived for two years, two months and two days, still draws nature lovers and deep thinkers.

The Wright Tavern, built in 1747, tells both sides of the story – American rebels planned their resistance here, and later British Lieutenant Colonel Francis Smith used it as his headquarters during the battle.