Things to Do on Cape Cod Thanksgiving Weekend | Pretty Picky
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Cape Cod Thanksgiving Activities

You came to Cape Cod this fall for fun, a four-seasons climate with beautiful fall colors, and a wide and varied array of activities only available on Cape Cod. The Pilgrims first landed in New England in the region of Cape Cod in the 1620s. Plymouth was the site of the first Thanksgiving, celebrated with the surviving Pilgrims from the Mayflower and nearly 100 Native Americans in celebration of the first harvest. Enjoy the traditional Thanksgiving meal, and learn even more about the area, Pilgrims, and more during your Cape Cod Thanksgiving visit.

Thanksgiving Dinner

The holiday we celebrate today is much different than that of the Pilgrims. They feasted and celebrated for three full days as a celebration of the harvest and was likely held sometime in late September or early November. Today, the restaurants that are open during the season celebrate with the traditional meal of today. Contact your restaurant of choice to see about hours and reservations.

Many restaurants are closed during the season, but some grocery stores remain open. Gather all the supplies you need to prepare and serve the meal and host the meal at your accommodation provided by Pretty Picky Properties.

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. The spot is a can’t-miss for your Cape Cod Thanksgiving adventure. There is handicap parking, boardwalk access to the sand, and more. Daily parking fee is $15 on weekdays and $18 on weekends.


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. Additionally, are a variety of companies in the towns of Cape Cod that offer guided tours of the area, hitting 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. Before making your plans, contact tour companies to ensure they are open and taking bookings.

Stellwagen Bank National Marine Sanctuary

The marine sanctuary is situated between Cape Cod and Cape Ann and consists of nearly 900-square-miles of area. The area is historically important as a fishing ground in the area. Currently, the sanctuary is New England’s only national marine sanctuary and is a premier destination for whale watching. It also continues to support commercial and recreational fishing activities. Take a whale-watching tour, go on a diving excursion in search of shipwrecks, or stay above water for birding and other things to do on Cape Cod Thanksgiving weekend. It is open ocean, meaning the only way to visit the area is by charter boat, which run on limited schedules in the fall.

Cape Cod National Seashore

Over half of the seashore’s land is accessed by the town of Wellfleet. 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 close to 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.


Part of Cape Cod’s beauty is its natural sand dunes. The dunes are part of the Cape Cod National Seashore along the coast of Provincetown. During the season, you can choose to take a tour of the dunes with a knowledgeable tour guide who provides information on local flora and fauna, as well as the history of the Dune Shacks, life-saving stations, and more.

During the off season, you can still explore the area.

Truro Vineyards

Set aside some adults-only time, as well as some good wine to add to your Thanksgiving feast! 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.

Cape Cod: Your Home for Thanksgiving

When planning your Cape Cod Thanksgiving retreat, make sure you choose a home base provided by Pretty Picky Properties. Choose from two-bedroom units for you and your small family or group this Thanksgiving all the way up to a ten-bedroom mansion to house all your loved ones to celebrate as the Pilgrims did. Prepare a delicious home-cooked meal, or the Thanksgiving feast, 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.

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