The Top Things to Do in Plymouth, Massachusetts

Built Structure By Sea In City Against Sky
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When the religious separatists we’ve come to call the “Pilgrims” made landfall at Cape Cod 400 years ago this November, it wasn’t the destination they’d been aiming for. Intending to settle near the Hudson River, they’d instead been diverted by stormy weather in their lengthy, 66-day Atlantic crossing. With winter coming fast, the Mayflower’s captain, fearing the treacherous coastline to the south, refused to sail any farther, forcing them to search nearby for a suitable site for their colony.

By chance, Captain John Smith had mapped the area four years earlier and had labeled one shoreline location “New Plymouth,” named for the city that had been the Pilgrims’ point of departure in England. The site met all their requirements, and in spite of the horrific first winter when literally half of the 102 Mayflower passengers perished, their little colony slowly began to thrive and grow. Now, four centuries later, Plymouth, the place that calls itself “America’s Home Town” is a quaint small city with a distinct New England character to it. It's a major destination in 2020 and beyond for travelers hoping to learn more about the Pilgrims’ quest for religious freedom and their life and death struggle to achieve it. Naturally, many of the highlights that can be seen in Plymouth are tied to the Pilgrims’ history.

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Take in the Harbor’s Highlights

Plymouth Rock
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Most people approach the stately portico covering Plymouth Rock expecting to see a huge boulder. And most people are shocked at how small it is. The legendary rock where the Pilgrims supposedly first set foot at their new home is only a fragment of its original size, portions of it having broken off when it was moved around the city several times before it was returned to its original location. In the years it sat in the town square, there was even a hammer and chisel stationed nearby for visitors to take home pieces of it as souvenirs! Nowadays, the Rock is visited each year by upwards of one million tourists, also eager to see the Mayflower II, the replica of the original ship England gifted to the U.S. in 1957.

02 of 10

Talk to the Pilgrims at Plimoth Plantation

Pilgrims Settlement
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Leyden Street in downtown Plymouth, sloping slowly uphill from the harbor to the town square, was the place the Pilgrims built their original homes. Their modest timber-framed houses with thatched roofs are long gone but are faithfully reproduced several miles outside of town at Plimoth Plantation, a living history museum using the spelling the Pilgrims’ governor, William Bradford, used in his journal. Characters in 17th-century garb representing the original colonists stroll the streets chatting with visitors.

I happen to share the name of one of the Pilgrims, so I sought him out, finding him to be a very friendly fellow in colorful dress (It’s a myth the Pilgrims wore only black and white), but I quickly found that any attempt to get him to break character was in vain. Asked about his modern descendants, which include Taylor Swift, Richard Gere, and Sarah Palin, he just shook his head in puzzlement. Throughout the village, visitors can participate in daily chores, engage in song and dance, or even participate in a muster drill. Nearby, a craft center houses artisans reproducing and selling 17th-century wares.

03 of 10

See Mayflower Artifacts at Pilgrim Hall Museum

If every artifact alleged to have arrived on the Mayflower had actually been on board, the cumulative weight would have sunk the ship. Pilgrim Hall, the oldest public museum in the U.S., is the place to see the largest number of artifacts in one place that truly were transported on the Mayflower, including William Bradford’s Bible, Myles Standish’s sword, and an exquisite wicker cradle that held Peregrine White, who was born on board the ship. Could the baby’s tiny toes have kicked the hole in the cradle’s foot?

Other exhibits include a sobering illustration of all 102 Mayflower passenger with the ones who didn’t survive the first winter grayed out. Poor Priscilla Mullins lost her entire family. A grand gallery with huge paintings include ones depicting the first Thanksgiving, the landing of the Pilgrims, and the signing of the Mayflower Compact, the document outlining the Pilgrims’ rules of governance. Planned exhibits for 2020 include The Plymouth Tapestry Project, a participatory embroidery project telling the story of early Plymouth.

04 of 10

Pay a Call at the Mayflower Society House

Mayflower Society House

Courtesy of Mayflower Society House

It’s estimated that 30 to 35 million descendants of the Mayflower passengers are alive today, and this exquisite mansion, built in 1754 by the great-grandson of Pilgrim Edward Winslow, serves as the headquarters of the Society of Mayflower Descendants, whose 30,000 members belong to 53 local chapters worldwide. Even those without a Pilgrim ancestor will find a docent-led tour through the house fascinating. Visitors can stand in the spot where Ralph Waldo Emerson married his bride, and see artifacts donated by Society members, such as a puritanical summons to a woman who missed church services, thus setting “an Evil Example to All Others.”

Architecturally, the rambling white house with a cupola on top is stunning, a “Flying Staircase” that splits and goes in different directions especially impressive. Outside, walk through a carefully tended garden with views of Plymouth Harbor to the research library where helpful librarians can show you how to begin the rigorous task of tracing your lineage back to one of the original Mayflower passengers.

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05 of 10

Take a Walk

Town Brook and Bridge in Brewster Gardens, Plymouth, Massachusetts, USA.
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All manner of guided tours are available in Plymouth, but one of the best walking tours is with guide Leo Martin from the Jenney Museum, which has exhibits conveying the impact the Pilgrims had on the founding of the U.S. It will lead you first along Town Brook, where natural springs bubble to the surface, down to the many statues and memorials lining the waterfront, regaling you all the way with historical tidbits you likely won’t hear elsewhere. Did you know that 14 of the 18 Pilgrim mothers starved the first winter, giving their children and not themselves the meager food that was available? Or that Myles Standish, commander of the Plymouth militia, was only 5 feet tall and was called “Captain Shrimp” behind his back?

For tales of a macabre nature, join Jan Williams on the “Dead of Night Ghost Tour.” The lantern-light tour departs from Plymouth Rock—just look for the hearse parked nearby. On the walk through the town center, you may well see ghostly apparitions peering out windows or hear a man with squeaky boots walking behind you. Inside the historic structures the tour stops at, the spirits occasionally run wild. Past participants have heard doors repeatedly slamming, seen their breath when the room suddenly grew cold, and even been engulfed by a black cloud. That little poke you felt on your shoulder? Don’t assume the person standing beside you was the guilty party.

06 of 10

Experience Grave Matters at Burial Hill

Old Plymouth Burial Hill
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Behind Plymouth’s town square, a steep hill abruptly rising to the height of 165 feet marks the site where the Pilgrims originally erected a stockade and meeting house. In the 1630s, however, the site began to be used as the town’s cemetery. Several of the Mayflower passengers were interred there, including Governor William Bradford, Church Elder William Brewster, and Mary Allerton, the last surviving passenger. Unfortunately, the headstones marking their graves have disappeared, making it possible only to guess the burial locations. Nevertheless, more than 2,000 elaborate headstones still cluster tightly on the 5-acre site marking deaths in Plymouth clear up to 1957 ranging from Revolutionary War veterans to mariners and missionaries. Monthly themed tours led by the Plymouth Antiquarian Society and Pilgrim Hall Museum use the gravestones as history lessons on subjects such as “Children in Early Plymouth,” “Unruly Women,” and “Plymouth’s Early Teachers” as well as giving overviews on the art of stone carving. Jan Williams’s ghost tour ascends the hill by cover of nightfall. Return in daylight to see the extraordinary views from the top.

07 of 10

Learn About the Native American History

Plimoth Plantation Recreates World Of The Pilgrims
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Many historians agree the Pilgrims’ colony likely would have perished altogether without the considerable help offered by the Wampanoags, a confederation of Native American tribes who’d lived in southeastern New England for tens of thousands of years. Wampanoags residing near Plymouth taught the Pilgrims how to fish and hunt and to grow the “three sisters” of corn, beans, and squash. Today, one of the best places to learn about the Native American culture is at the “Wampanoag Homesite” at Plimoth Plantation, where members of still-existing local tribes can be seen burning and scraping dugout canoes; cooking duck, fish, rabbit, and quail on spits; and making dolls. Go inside the bark-covered long house to meet local Wampanoag tribespeople dressed in traditional costume, discussing their history and efforts to retain their culture.

A traveling exhibit called “Our Story: 400 Years of Wampanoag History” will circulate throughout Massachusetts during this anniversary year, including to Plymouth.

08 of 10

Take an Aquatic Excursion

Provincetown, Cape Cod
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Several tours operate out of Plymouth’s lovely harbor going out into Cape Cod Bay and beyond. Captain John Boats Whale Watching & Deep Sea Fishing allows the opportunity to see humpback, minke, and finback whales or to fish for haddock, pollock, mackerel and flounder. Plymouth Cruises takes visitors on themed journeys including a Pirate Cruise, a Lobster Excursion, and Ice Cream or Wine Tasting Cruises.

But visitors wanting to investigate the Pilgrim Heritage further will want to take the “Fast Ferry” with Captain John Boats out to Provincetown on the tip of Cape Cod, the place where the Pilgrims made their first landfall. The dramatic pencil-thin 262-foot-high Pilgrim Monument in “P-town,” as Provincetown is called locally, has commemorated this heritage since 1910. From the top, spectacular views of most of Cape Cod can be seen. Summertime walking tours of the lovely town leave from the museum’s base.

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09 of 10

Explore the Region

Corralled Cranberries
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Conveniently located south of Boston and at the approach to Cape Cod, Plymouth offers ample excursions for day trips. It’s easy to use Plymouth as a base to explore the Cape’s many beaches and small towns, and just to the west, “Cranberry Country” offers cranberry harvest festivals and bog tours. Just to the north in the neighboring town of Duxbury, tours of the Alden House tell the love story of Pilgrims John Alden and Priscilla Mullins, as well as fascinating stories of their descendants who occupied the home, including two brothers who hated each other so much they built a barrier through the middle of the house so they could avoid one another. The home has the distinction of being the oldest colonial homesite continuously owned by descendants of its original Pilgrim family. Today, as many as a million Americans can trace direct lineage to this couple who found love after their arrival in the New World.

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Enjoy Anniversary Events

As epicenter for America’s “Mayflower 400” celebrations, Plymouth had scheduled a number of special events throughout 2020. Although many of them have been cancelled or postponed, you can find an updated schedule of events here. Plymouth’s Thanksgiving observations will now be held virtually, including performances, special ceremonies, and more. Expect more events in 2021, when the Pilgrims’ first Thanksgiving will celebrate its 400th birthday.

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