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Historical Sites in Cape Cod Journey

You came to Cape Cod for fun, its four-seasons climate, and the sand and water at the beach along the Atlantic Ocean. It has a rich history dating back to the Pilgrims and Native Americans. Take some time out of your busy schedule to appreciate some of the historical sites in Cape Cod that helped build the country into what it is today.

Day 1: Beaches

First Encounter Beach

The Eastham beach is said to be the site of the Pilgrims’ first encounter with Native Americans upon arriving in the New World. They arrived in the spot after leaving Provincetown and before landing at Plymouth. The mostly calm, warmer waters (in summer) of Cape Cod Bay make it a great beach spot for families with young children. You can make use of the bathhouse and other facilities. There is handicap parking, boardwalk access to the sand, and more. Daily parking fee is $15 on weekdays and $18 on weekends.

Mayflower Beach

Head to Dennis for this beach named after the boat that brought the Pilgrims to the New World. The patch of sand offers access to the waters of Cape Cod Bay. The beach boasts a boardwalk that runs from the parking area all the way to the sand. It’s a perfect spot for vacationing families, especially in the warmer months. You’ll find a volleyball net up on the western side of the beach, restrooms, concessions, and lifeguards on duty. In-season parking is $15/day.

Day 2: Historic Buildings

Chatham Lighthouse

The lighthouse was originally part of a pair of lighthouses. The one that remains in Chatham today is in operation 24 hours a day, guiding boats away from the rugged cliffs of the Cape Cod Atlantic. The other was pulled and painted a bold red and white before becoming the Nauset Lighthouse. Nearby the Chatham light is a Coast Guard station, staffed by a crew ready to answer the calls of distressed mariners. Tour the lighthouse during the summer season, at First Night, or visit the grounds any time you wish to learn more about Cape Cod history. You can even make it part of your visit to Chatham Lighthouse Beach.

Barstable Old Gaol (Jail)

Visit the oldest jail in the United States and one of the best historical sites in Cape Cod! Originally residing on Old Jail Lane in Barnstable Village, the structure currently stands on the grounds of the Coast Guard Heritage Museum. The old, historic wooden structure is open for tours during the season (May-October). The building resembles a colonial domestic residence and was built by order of the Plymouth and Massachusetts Bay Colony courts in 1690. It served as the primary jail until 1820. The six cells remain intact, and have their original locks, hinges, and iron bars.

Jonathan Young Windmill

The Orleans windmill was built in the early 1700s to cure the lack of fast-running rivers and streams in the area and used to turn millstones to grind grain. In 1839, the structure was moved to overlook the Town Cove on the present hillside site of the Governor Prence Motor Inn, on Route 6A. It was relocated once more to its current location in an effort to restore the structure. The site is open for tours in July and August.

Day 3: Historic Homes

Crosby Mansion

The home was built in 1888 in Brewster by Albert and Matilda Crosby. The mansion was nicknamed “Tawasentha” based on an excerpt from Henry Wadsworth Longfellow’s “Song of Hiawatha” poem. The Colonial Revival-style home also incorporated design elements of French, Asian, and multiple other influences. It included indoor plumbing and gas light and became first home on Cape Cod to incorporate the features. Tours are offered of the three-story home in the summer and fall with a $6 donation to the restoration effort.

Atwood Museum

Residing in the 1752 home of Captain Joseph Atwood in Chatham, the museum is a collection of historic objects and the records of the town’s history. The original home remains, but additions and restoration efforts have been made over the years. The museum hosts events, programs, and education seminars that bring visitors and locals alike closer to the town’s history.

Edward Gorey House

When author and artist Edward Gorey purchased the home in 1979, it was already over 200 years old. The home in Yarmouth was Gorey’s residence and where he worked on many of his books before his passing in 2000. The home then became a museum of Gorey’s life and work with regular exhibits, as well as special events like “Dressed to Kill: Edward Gorey and the Social Fabric” – looking into the use of Gorey’s personal fashion and the importance of his characters’ wardrobes.

Experience Historical Sites in Cape Cod

When you stay in a vacation rental in Cape Cod provided by Pretty Picky Properties, you’ll enjoy easy access to the beach and the crashing waves of the Atlantic, and its history. We’re also close to many area attractions, sites, tours, shopping, dining, and activities the area has to offer. We offer two-bedroom units for your small family getaway all the way up to a ten-bedroom compound for a Cape Cod history-lover’s getaway with all your loved ones. Prepare a delicious home-cooked meal in the fully equipped kitchen. Afterward, spread out in an open living space for a movie or to relax. Enjoy the view from the private balcony or patio or spend some time near the pool at select rentals.

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