Take a Sightseeing in Cape Cod Journey | Pretty Picky
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Sightseeing on Cape Cod Journey

You came to Cape Cod for fun, a four-seasons climate, as well as the sand and water at the beach along the Atlantic Ocean. Make sure to see the sights and take in some history while you’re here. There are plenty of historic and important sights to add to your sightseeing in Cape Cod trip, and you’ll want to make sure to spend some time at each.

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) make it the perfect beach 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.

Cape Cod National Seashore

Much of the seashore is accessed by the town of Wellfleet – over half! The CCNS was created in August of 1961 by President John F. Kennedy and includes ponds, woods, and beachfront along the Atlantic coastal pine barrens ecoregion. It is nearly 40 miles of seashore along the Atlantic-facing eastern shore of the Cape Cod region, spanning the towns of Provincetown, Truro, Wellfleet, Eastham, Orleans, and Chatham.

Day 2: Historic Homes

Crosby Mansion

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, the first home on Cape Cod to incorporate the features. Tours are offered of the three-story home in the summer and fall, and a $6 donation to the restoration effort is appreciated when you visit this home on your Cape Cod trip.

Atwood Museum

Residing in the 1752 home of Captain Joseph Atwood, the museum is a collection of historic objects and the records of Chatham’s history. The original home remains, but as the museum and its mission expanded, additions and restoration efforts were made. The museum hosts events, programs, and education seminars that bring visitors and locals alike closer to the town’s history with each visit.

Edward Gorey House

The home was over 200 years old when author and artist Edward Gorey purchased the home in 1979. 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 as well as the importance of his characters’ wardrobes.

Day 3: Historic Buildings

Chatham Lighthouse

Originally part of a pair of lighthouses, the light is currently in operation 24 hours a day, guiding boats away from the rugged cliffs. One remains standing in Chatham today, while the other was pulled and painted a bold red and white before becoming the Nauset Lighthouse. Nearby is a Coast Guard station, staffed by a crew ready to answer the distress calls of mariners. Tour the lighthouse during the summer season, at First Night, or visit the grounds any time you wish when you’re sightseeing on Cape Cod. You can even make it part of your visit to Chatham Lighthouse Beach next door.

Barnstable Old Gaol (Jail)

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

Jonathan Young Windmill (Orleans)

The Orleans windmill was built in the early 1700s as an answer to the lack of fast-running rivers and streams in the area. It was 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 again to its current location due to restoration efforts. The site is open for tours in July and August.

Sightseeing in Cape Cod

When you stay in a vacation rental on Cape Cod provided by Pretty Picky Properties, you’ll enjoy easy access to the beach and the crashing waves of the Atlantic. 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 sightseeing 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.

Contact us today to start planning your Cape Cod sightseeing journey!

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