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Touring history

Explore the Cape & Islands on these historical walking tours

historical walking tours

A good pair of walking shoes and an appetite for history are all you’ll need for these enriching town tours.

There’s no better way to get to know Cape Cod than by taking a leisurely walk or drive. It’s like a little adventure. You never know what you might discover along an unassuming side road.

You can tell a lot about a Cape Cod town and its people simply by looking. How many churches are there, and what denominations do they represent? Is there a “downtown” and if so, what is it like? How wide are the streets? How big are the houses, and what are they made of? How old are the trees?

You can discover even more if you travel with a local guide, preferably one brimming with stories and fun facts about the winding streets and crooked buildings. In the summer, several Cape Cod history museums offer tours of their host towns to engage the community and advance their mission of historic preservation. Here are three popular museum-sponsored tours—in Falmouth, Brewster and Nantucket—that illustrate how the past continues to inform and shape life on the Cape today.

Brewster: The world of Lyddie Berry

historical walking tours

19th century barn on the property of the Dillingham House, c.1660, is the oldest house in Brewster. Note the outhouse at the far left.

“Brewster is interesting because it’s got architecture from every age,” says Sally Cabot Gunning, award-winning author and president of the Brewster Historical Society. “It’s like a map of all the years.”

Because the town is quieter and less developed than most on the Cape, it’s still possible to find roads lined exclusively with the old, tiny cottages and Capes that once dominated the entire landscape here. “There are pockets of Brewster that are developed, but it’s nice that it’s not all of Main Street,” says Gunning.

Since there is no real downtown, an architectural excursion through Brewster is better suited to a bike or car. The Brewster Historical Society runs two different bus tours every August and September, the Sea Captain’s Tour and the Widow’s War Tour, each focusing on a different era. The Sea Captain’s Tour highlights the Cape’s maritime history, while the Widow’s War Tour follows the 18th-century narrative of Gunning’s popular historical novel The Widow’s War. As the novel begins, protagonist Lyddie Berry is widowed (her husband dies at sea). “As people take the tour, the narrator is telling Lyddie’s story,” says Gunning. “People come because they’ve read the book. People come because the tour sounds interesting, and they want to read the book when they are done.”

Many historic homes and landmarks that Gunning mentions in her novel are stops on the tour, as the bus retraces Lyddie’s fictitious steps. It’s an imaginative game to play. Where would she have gone to church? Where did she live? What harbor would she have walked to? At several stops guests disembark from the bus to walk in and around the antique buildings. One stop is Hopkins Bakery, which offers not only complimentary baked goods but also a mini-tour of the Stephen Hopkins house, owned by the grandson of the famous Mayflower family of the same name. The bus tour ends at the newly renovated home of the Brewster Historical Society, the elegant Captain Elijah Cobb House, where Gunning herself meets guests in the parlor to chat and sign books.

The idea for the tour arose when the paperback edition of The Widow’s War was being prepared for release. “My editor asked me to include additional historical material in the back of the book. So I put together a driving tour,” explains Gunning. “They were selling the book at bookstores in town. They said, ‘We need the tour! People are asking for the tour!’ It’s one of our best fundraisers for the society.”

For the do-it-yourself visitor, the Brewster Historical Society also offers a map with a self-guided driving tour, available for sale at the museum.

Falmouth: Militiamen, sea captains & a famous poet

historical walking tours

The Falmouth First Congregational Church today. If time and schedule allows, visitors often get to go inside the First Congregational Church, one of the hallmark sites of Falmouth’s Historic Village Green. Photo courtesy of the Falmouth Historical Society.

Minus the streetlights, power lines, and paved roads, many historic areas of Cape Cod look very much as they did 100 or even 200 years ago. This is especially true of Falmouth’s Village Green and surrounding houses. “I’ve picked out photographs over 150 years old that I recognize and I bring people to that spot,” says Tom Mountford, a volunteer docent at the Falmouth Museums on the Green. “You can get an idea of really how little the town has changed.”

The museum, operated by the Falmouth Historical Society, offers walking tours every Tuesday and Thursday morning from June to mid-October. Each tour explores Falmouth’s history through its architecture and geography, focusing on the 17th century to the present.

“Our walking tour centers around the Village Green, where members of the colonial militia practiced in the 1700s and sea captains built their homes,” says Mark Schmidt, the museum’s executive director. Lined with stately two-story square-riggers and a handful of Victorians and Capes, the green was the town’s early hub of wealth, politics and religion. Stories of the men and women who built, walked, gathered, worked, and died there are reflected in the surrounding houses, roads, ponds, and open spaces. The tour also takes in the birthplace of Falmouth’s famous daughter, Katharine Lee Bates, a poet and songwriter who penned “America the Beautiful,” along with two historic churches: the First Congregational Church, dating from 1796, and St. Barnabas Episcopal Church, built in 1888.

Mountford, a retired Falmouth police officer who can also be found running the drawbridge in Woods Hole, has been leading walking tours for over 10 years. One of his favorite stops is the Old Burying Ground, located just off Siders Pond, about a half-mile from the Village Green. The Old Burying Ground was the colonial settlers’ first town center. Epitaphs on graves dating back to the 18th century reveal details of what life was like for a tiny seafaring village perched on the southern tip of Cape Cod.

“Over the years I’ve found a few headstones that say ‘lost at sea’ or ‘killed by whales,’” says Mountford. “There is a 16-year-old boy that fell from the ship’s rigging and landed on deck. Another one—Chadwick I think is his name—was lost at sea off the coast of Chile. He was on the Commodore Morris, a whaleship built in Woods Hole. A Falmouth-built boat with a Falmouth guy, lost off the coast of Chile in the Pacific Ocean on a whaling trip. Brings it home a little bit.”

Mountford is one of many dedicated volunteers who bring the town’s history to life. “We are extremely fortunate to have tour guides who not only possess an intimate knowledge of Falmouth but also great people skills, making the experience even more enjoyable,” says Schmidt. “Whether you’re a visitor to Falmouth or a resident, you’re guaranteed to learn something new.”

For those wishing to cover more distance, the museum also offers a trolley tour on Wednesday mornings in September and October. Adding the late 19th and 20th centuries to the narrative, it winds through Falmouth Heights, follows the shore to Nobska Light, and stops at Highfield Hall & Gardens, the Victorian-era mansion turned cultural center.

Nantucket: Quakers & whalers

historical walking tours

Pictured on the right: Nantucket’s Counting House, built in 1772

A distinct and singular world 30 miles south of the peninsula, Nantucket has its own aesthetic and customs. A tour of the downtown with Linda Steelman, senior interpreter from the Nantucket Historical Association, shows how truly different it is, beginning with the architecture—the brick storefronts, the “friendship stairs” leading to raised front doors, the grand Greek Revival mansions, and the three-story captains’ houses. And of course, those cobblestone streets and rippling sidewalks.

The island’s vernacular architecture is intertwined with its history, most notably its whaling heritage and Quaker underpinnings. To present this story with up-close experiences inside the distinctive buildings, the historical association offers a Historic Downtown Walking Tour twice daily from May to the end of October.

The heyday of Nantucket’s whaling era, the middle of the 19th century, sets the stage for the tour. At that time, the whaling industry saturated all aspects of island life. It affected the diversity of the people who inhabited the island, the evolution of the buildings, and the explosive growth of associated businesses such as refineries, coopers, outfitters, and candle factories. The island’s imported Quaker beliefs informed the ways in which islanders conducted their business, studied, and socialized.

With eight to nine stops on the tour, including several properties owned and maintained by the historical association, participants get to visit buildings such as the Quaker Meeting House and the William Hadwen House. Hadwen was a 19th-century entrepreneur who invested in the lucrative whaling industry. His mansion is both a testament to his wise business investments and a window into high Nantucket living in the 19th century.

The tour meanders down Center Street, or “Petticoat Row” as it was commonly known, named for the many women business owners on the street. It was rare for a woman to own a business in the 19th century; the high number of women-owned business on Nantucket is attributed to the Quaker emphasis on education and equality.

“In the 18th century, a Quaker woman could travel unescorted. She would have a little passport so she could leave the island and travel to a Quaker meeting in Boston,” explains Steelman. “This was really shocking and quite forward thinking, and it made for a very independent woman on island, which is a part of her heritage even today. The head of our government is a woman. We have a lot of women business owners. I’ve never lived in a place where that has been more palpable.”

Steelman, who has been working as an interpreter at the historical society for 17 years, recounts her Nantucket anecdotes with a twinkle in her eye. Her curiosity is infectious. “When a lot of tourists come to Nantucket, they get off the boat and they shop and they like the charm,” she says. “But it’s going on a walking tour where you really start digging into the sand, getting the real gems and bringing up all that richness that makes Nantucket so unique.”


  • The bell in Falmouth’s First Congregational Church was made by Paul Revere and dates to 1796. It still tolls today.
  • The oldest house in Brewster is the Dillingham House, a saltbox built in 1660.
  • Saltbox houses were always built facing south so that the long roof protected the house from the brutal winter winds from the north.
  • The entire island of Nantucket is a National Historic Landmark and is the largest historic district in the country.
  • You can date an antique barn by the location of its door. In the 18th century, barn doors were built on the long sides of the barn. In the 19th century, they were built on the short sides.
  • Nantucket’s schools were first integrated in 1847, more than 100 years before the landmark Supreme Court ruling in Brown v. Board of Education.
  • Absalom Boston, a black resident of the New Guinea neighborhood on Nantucket, was the first black captain of an all-black whaleship, The Industry, from 1819 to 1821.
  • There are 121 buildings in Barnstable County listed on the National Register of Historic Places.
  • Nantucket has over 800 homes built between 1750 and 1850.
  • On Nantucket, additions on houses are affectionately called “warts.”
  • Wing Island, the site of the Cape Cod Museum of Natural History in Brewster, is named for John Wing, a Quaker and one of Brewster’s first colonial residents, who settled there in 1659.

Amanda Wastrom is a curator, artist, and writer living in East Sandwich.

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