Check Out These President’s Day Things to Do in Cape Cod | Pretty Picky
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President’s Day Things to Do in Cape Cod

You came to Cape Cod this President’s Day for fun, a four-seasons climate, and a wide and varied array of things to do in Cape Cod. There are a variety things to do and places to see, including some with a presidential flair, to make your retreat one to remember for a lifetime!

John F. Kennedy Hyannis Museum

The most famous president with ties to the area is 35th President John F. Kennedy, better known as JFK. The museum is devoted to his life and legacy. 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.

Contact the museum before you make plans. Tentative hours are Monday-Saturday 10 a.m. – 4 p.m. but may change.

Cape Cod National Seashore

President Kennedy left his mark on Cape Cod in an everlasting way. Much of the seashore is accessed by the town of Wellfleet – over half of the designated land is there! The CCNS was created in August of 1961 by President Kennedy. The area 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.

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. The site is where the Pilgrims landed after leaving Provincetown and before arriving in Plymouth. The mostly calm waters make it the perfect beach for families with young children this Cape Cod President’s Day.

While it will be too cold for typical beach things to do in Cape Cod, the historic site is not to be missed. 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. Pack up the rental car and plot your own course or book a sightseeing tour and let someone else do the driving. Tap any of the number 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 from any daytime tour.

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

Truro Vineyards

Set aside some adults-only time this President’s Day and enjoy some good wine! Wine tastings are offered by the glass daily, year-round. 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: President’s Day on Cape Cod

When planning your Cape Cod President’s Day retreat, make sure you choose a home base even a president would choose: one provided by Pretty Picky Properties. 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 meal of your own in the fully equipped kitchen. Lounge inside in beautiful living spaces or enjoy the view and crisp New England air from the private balcony or patio or spend some time near the pool at select rentals.

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