Cape Cod Labor Day Activities and Events Happening This Year | Pretty Picky
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Cape Cod Labor Day Activities

Enjoy a long holiday weekend in a four-seasons climate that’s starting to head toward fall. Labor Day Weekend bids farewell to summer for many and is one last chance to enjoy the warmer weather it brings. The cozy towns of Cape Cod help you celebrate, with a myriad of Cape Cod Labor Day activities, as well as year-round fun that you can enjoy no matter when you visit.

Cape Cod Labor Day Weekend Craft Festival

Enjoy the rest and relaxation of a long weekend, along with fun arts and crafts. The event features over 90 artisans, craftspeople, and vendors showing off handmade fine jewelry, candles, textiles, sea glass, turned wood, resin creations, art, photography, and more. Taste specialty foods including kettle corn, oils, jams, jellies, nut butters, whoopee pies, dessert mixes, and so much more.

Free, on-site parking is available and well-behaved, leashed dogs are welcome. The admission-free Labor Day event on Cape Cod takes place August 31 10 a.m. – 5 p.m. and September 1 10 a.m. – 4 p.m., rain or shine. Visit them at Simpkins Field, 1153 Rt. 28 in South Yarmouth.

West Dennis Beach Party, Bonfire & Fireworks

The free event features a beach party, as well as evening bonfire and fireworks along West Dennis Beach. Dance to live music, roast marshmallows at the bonfire, and set up your seats for the fireworks display starting at dusk (around 8:30 p.m.).

There will be a free shuttle bus starting at 5 p.m. from Ezra Baker School, as well as the West Dennis Graded School. Another good fireworks viewing spot is Smugglers Beach in South Yarmouth. The party starts at 5 p.m.

Sightseeing Tours

There are a variety of historic and other significant sights scattered across Cape Cod you’ll want to make a part of your Labor Day itinerary. Pack up the rental car and plot your own course or book a sightseeing tour so everyone can relax and enjoy the journey.

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. Knowledgeable guides will take you to all the places you want to go and fill you in on local history and Labor Day events on Cape Cod. Choose 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.

John F. Kennedy Hyannis Museum

The museum is devoted to the life and legacy of America’s 35th It includes exhibits like a remembrance of the fateful day in 1963 when President Kennedy (JFK) was shot, the presidential summer home, and personal belongings, including his rocking chair – known as a Kennedy Rocker – which is on loan due to the renovation of The Towers of the Waldorf Astoria.

Holiday hours are Monday-Saturday, 10 a.m. – 4 p.m. Check to make sure the tour is available on Labor Day. Tickets and admission prices are available on the museum website.

Cape Cod National Seashore

Much of the seashore is accessed by the town of Wellfleet. In fact, over half of the designated land is within the town’s borders! The CCNS was created in August of 1961 by 35th President John F. Kennedy, and includes natural features like 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 Cape Cod, and includes the towns of Provincetown, Truro, Wellfleet, Eastham, Orleans, and Chatham.

Truro Vineyards

Set aside some adults-only time this Cape Cod Labor Day, 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. Currently they are open Monday-Saturday 11 a.m. – 5 p.m., and Sunday 12-5 p.m.

First Encounter Beach

While it may be a bit cool for a swim or other beach activities, you’ll want to see the Eastham beach is reported to be the site of the Pilgrims’ first encounter with the Nauset Native Americans upon arriving in the New World.

The Pilgrims arrived in the spot after leaving Provincetown and before arriving in Plymouth. There are facilities including a bathhouse and restrooms, in case you do plan a Labor Day beach day. There is handicap parking, boardwalk access to the sand, and more. Daily parking fee is $15 on weekdays and $18 on weekends.

Labor Day Accommodations on Cape Cod

When planning your Labor Day vacation to Cape Cod, make sure you choose a home base provided by Pretty Picky Properties. We offer two-bedroom units for a smaller family Labor Day getaway, all the way up to a ten-bedroom mansion to house all of your loved ones for a Labor Day Weekend reunion.

Prepare a delicious home-cooked meal, or fixin’s for a Labor Day cookout, 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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