Have a Fall in Cape Cod Journey | Pretty Picky
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Fall in Cape Cod Journey

You came to Cape Cod this fall for fun, a four-seasons climate with beautiful fall weather, and a wide and varied array of activities only available on Cape Cod. There are a variety of things to do and places to see to make your fall in Cape Cod retreat one to remember for a lifetime!

Day 1:

First Encounter Beach

The Eastham beach is reportedly the site of the Pilgrims’ first encounter with the Nauset Native Americans upon arriving in the New World. They arrived in the spot after leaving Provincetown and before arriving in Plymouth. The mostly calm waters make it the perfect beach for families with young children. You can make use of the bathhouse and other facilities. You may want to limit your beach activities like swimming and sunbathing as the weather cools, but the spot is a can’t-miss for your Cape Cod adventure. There is handicap parking, boardwalk access to the sand, and more. Daily parking fee is $15 on weekdays and $18 on weekends.

Sightseeing Tours

There are a variety of historic and other significant sights scattered across Cape Cod. Get in your car and plot your own course or book a sightseeing tour and let someone else do the driving. There are a variety of companies in the towns of Cape Cod that offer guided tours of the area, hitting on all the hot spots. The knowledgeable guides will take you to all the places you want to go and fill you in on local history and events. Select a specialty tour that includes food or wine tastings, sunset tours, or even night tours that offer a different perspective than any daytime tour can offer.

Day 2:

John F. Kennedy Hyannis Museum

The museum is devoted to the life and legacy of America’s 35th President. It includes exhibits like a remembrance of the fateful day in 1963 when President Kennedy was shot, the presidential summer home, and personal belongings like his rocking chair – known as a Kennedy Rocker – on loan due to the renovation of The Towers of the Waldorf Astoria. October hours are Monday-Saturday 10 a.m. – 5 p.m. November hours are Monday-Saturday 10 a.m. – 4 p.m., and December hours are Thursday-Saturday 10 a.m. – 4 p.m. The museum is open for shortened hours on Veterans Day and Black Friday, but is closed Thanksgiving, Christmas, and New Year’s Day. Tickets and admission prices are available on the museum website.

Woods Hole Science Aquarium

Established in 1875, the aquarium is the oldest public aquarium in the U.S. It hosts approximately 80 species of marine animals native to the Northeast and Mid-Atlantic U.S. waters. It is designed for self-guided tours of the main exhibits, while visitors can also get a behind-the-scenes look at aquarium operations. There is also a seal enclosure hosting several residents. Current operating hours for the seal enclosure as well as the indoor aquarium are Monday-Friday 11 a.m. – 4 p.m. The upstairs gallery, touch tank, and other exhibits are currently closed for construction.


Anglers on a fall respite to Cape Cod won’t be able to resist casting a line. The area is ripe with great fishing spots, including great places for shore fishing, freshwater fishing, and of course, deep sea fishing. You’ll hook catches like striped bass, flounder, bluefish, flatfish, smallmouth and largemouth bass, and many more. Check out shore fishing hot spots like Cape Cod Bay or Brewster Flats. Freshwater locales include Nickerson State Park, Long Pond, and Black Pond.

Day 3:

Cape Cod National Seashore

Much of the seashore is accessed by the town of Wellfleet – in fact, over half of the designated land is there! The CCNS was created in August of 1961 by 35th President John F. Kennedy and includes ponds, woods, and beachfront along the Atlantic coastal pine barrens ecoregion. The CCNS is nearly 40 miles of seashore along the Atlantic-facing eastern shore of the Cape Cod region, and includes the towns of Provincetown, Truro, Wellfleet, Eastham, Orleans, and Chatham.

Truro Vineyards

Set aside some adults-only time, as well as some good wine! Wine tastings are offered by the glass daily. There is also a pavilion with walk-up bar. Grapes are grown right on the five-acre vineyard and include Chardonnay, Cabernet Franc, and Merlot. Choose from a variety of reds and whites or try something from the “Lighthouse Wine Series” or “Limited Release Wines.” The vineyard also offers a selection of spirits, including whiskey, gin, rum, and Amaro. The vineyards are open year-round, and hours vary throughout the year. Typical summer and fall hours are Monday-Saturday 11 a.m. – 5 p.m. and Sunday 12-5 p.m.

Destination: Fall in Cape Cod

When planning your Cape Cod fall journey, make sure you choose a home base provided by Pretty Picky Properties. For your fall retreat, we offer two-bedroom units for you and your small family or group all the way up to a ten-bedroom mansion to house all your loved ones. Prepare a delicious home-cooked, soul-warming fall meal of your own in the fully equipped kitchen. Lounge inside in beautiful living spaces or enjoy the view from the private balcony or patio or spend some time near the pool at select rentals.

Explore an array of Cape Cod vacation rentals, including inviting West Barnstable vacation rentals, charming Eastham vacation rentals, and scenic Wellfleet vacation rentals.

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