You came to Cape Cod for plenty of fun, a four-seasons climate, and a wide and varied array of outdoor adventures and activities only available on Cape Cod. There are a variety of things to do and places to see to make your ultimate outdoor Cape Cod adventure and retreat one to remember for a lifetime!

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First Encounter Beach

The beach in Eastham is reportedly the site of the Pilgrims’ first encounter with the Nauset Native Americans upon arriving in the New World. The Pilgrims arrived at the spot after leaving Provincetown and before arriving in Plymouth. The mostly calm waters of the area make it the perfect beach for families with young children. Make use of the bathhouse and other facilities for your comfort. There is handicap parking, boardwalk access to the sand, and more. The daily parking fee is $15 on weekdays and $18 on weekends during the season.

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. Tours include a number of outdoor sites where you can get out, stretch your legs, and explore the great outdoors of Cape Cod.

There 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 along the way, sunset tours, or even night tours that offer a different perspective than any daytime tour can offer.


Anglers on an outdoor adventure to Cape Cod won’t be able to resist casting a line. The region 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 others. Check out shore fishing hot spots like Cape Cod Bay or Brewster Flats. Freshwater locales include Nickerson State Park, Long Pond, and Black Pond.

Cape Cod National Seashore

Much of the official seashore is accessed by the town of Wellfleet – in fact, over half of the designated land is there! The CCNS was created in August 1961 by 35th President and Massachusetts native 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. It includes the towns of Provincetown, Truro, Wellfleet, Eastham, Orleans, and Chatham.

Truro Vineyards

Set aside some adults-only time during your outdoor adventures and take the time to taste some good wine! Wine tastings are offered daily by the glass. There is also an outdoor 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.

Deep Sea Fishing

Heading out to the depths of the Atlantic can be a thrilling way to catch your next big fish story. Headboats, or “party boats,” offer a variety of trips, from short, fun trips where you can catch your next meal, to longer trips like full day or overnight fishing treks.

Set your sights on hooking fluke, cod, haddock, mahi, swordfish, wahoo, tuna, and many others. For a different thrill during your deep-sea excursion, ask about shark fishing!

Cape Cod Rail Trail

The over 25 miles of paved paths offer challenges for serious bikers as well as more tame routes for adventure-seeking families. The trail stretches through seven Cape towns: Yarmouth, Dennis, Harwich, Brewster, Orleans, Eastham, and Wellfleet. The trail gets its name from its location: it sits atop a former railroad line. The trail cuts through parks, past dazzling bodies of water, and a unique variety of ecosystems.

You’ll find many people biking the path, but there are also visitors walking, jogging, running, rollerblading, horseback riding, and even Nordic skiing in the winter! The trail is open daily dawn to dusk, and there are eight different entry points along the trail, each with a convenient parking area.

Monomoy National Wildlife Refuge

The refuge is not only the perfect place for wildlife to while away the time, but human visitors, too. The federal refuge on Monomoy Island was established in 1944 to provide a safe habitat for migratory birds. These habitats combine to provide a safe harbor for over 25 species of seabirds, shorebirds, waterfowl, and other visitors.

The refuge itself is situated on an eight-mile stretch of sandy beaches in Chatham and boasts over 7,600 acres of beaches, trail systems, and a variety of habitats and ecosystems. Its waterways include parts of the Atlantic Ocean, salt and freshwater marshes, and freshwater ponds. You won’t want to forget to check out the dunes, too. Activities available in the refuge include birding, fishing, hiking, shellfishing, photography, and more.

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 outdoor activities in Cape Cod.

Shining Sea Bikeway

Head to Falmouth for another beautiful biking experience. The 10+ mile long trail starts at the Steamship Authority Ferry Terminal, snakes through breathtaking lands, and finally ends at Woods Hole in North Falmouth.

The paved path’s name hearkens from a line in the song America the Beautiful “From sea to shining sea…” The bikeway runs along the Atlantic Ocean shoreline offering a glimpse of the shining sea it speaks of. It winds along the Vineyard South Shoreline, past Woods Hole, through cranberry bogs, and more as it overlooks Chapoquoit Beach.

Nickerson State Park

The public recreation area offers over 1,900 acres of wooded coastal land in the town of Brewster. Explore the woods, take in the kettle ponds, or participate in one of the park’s many outdoor activities in Cape Cod. You’ll find visitors hiking, fishing, boating, cross-country skiing, horseback riding, swimming, kayaking, playing basketball, and biking. Other facilities include an amphitheater, restrooms, picnic pavilions, and playgrounds for the kids.

Highfield Hall and Gardens

Wander the 18th century estate that is open early spring to early fall. Tag along on heritage and garden tours or attend a special event like a concert or show. Walk the pathways of lovingly and beautifully restored and maintained gardens or explore with a trail walk through nearby Beebe Woods.

Take some time out for a picnic, then wander to the property’s Music Garden, a place where kids and kids-at-heart can make beautiful music with built-in instruments.

Heritage Museum & Gardens

The property is a cozy 100 acres of land dotted with trees, shrubs, and flowers in Sandwich, but that doesn’t mean you should leave it off your list. Wander the peaceful gardens, walking trails, and more as you take in the sounds and scents of a New England spring or summer.

Explore multiple gardens, including the rhododendron garden, herb garden, and Cape Cod hydrangea display garden, or check any of the bee hotels for residents. Take a ride on the 1908 Looff carousel,

If by chance you do want to escape the weather, the museums are a sight to see as well. Exhibits include information about the transformation the automobile brought to America, as well as early electric cars in America, Impressionist New England, and more.

Opening day is April 20, 2024.

Mayflower Beach

The Pilgrims sailed to the New World aboard the Mayflower, and a beach in Dennis bears the name of the famous ship. The beach stretches along the shores of Cape Cod Bay. Enjoy the day at the beach, with activities including a boardwalk from the parking area to the beach, volleyball, and more. During the season there is a lifeguard on duty, as well as concessions and restrooms. In-season parking is $15/day.


While going inside each one isn’t the “outdoor adventure” you’re looking for, finding and visiting all of Cape Cod’s lighthouses will give you plenty of time outside in the fresh New England air. Make a list that includes Nobska Point, Chatham, Nauset, Highland, the Three Sisters Lighthouses, Wood End, and more. Ask us about other must-see lighthouses.

The areas around the lighthouses are often open 24 hours a day, year-round, but the lighthouses themselves aren’t open for touring until the summer season.


The outdoor activity will keep you busy in the fresh New England air for hours. Challenge yourself to one of the many golf courses in the area. While it may not be the “adventure” you’re looking for, it’s time well spent during your time on Cape Cod.

Contact the course of your choice and book a tee time. If your clubs and other golf gear don’t make the packing list, ask about rentals or the best place to purchase what you need.

Sandwich Fish Hatchery

While there are hundreds of species of fish in the sea – the Atlantic Ocean off the coast of Cape Cod to be exact, the State of Massachusetts is giving its freshwater species a little push in numbers. There are a total of five hatcheries across the state, including one on Cape Cod. Between the five, over 500,00 brook, brown, rainbow, and tiger trout are stocked into state waterways during spring and fall stocking seasons.

Make a visit to the hatchery to view the fish at their different stages of growth, and before they’re released into the waterways. Visits are self-guided, so take as much time as you wish to learn and explore. There is parking available onsite.

Uncle Tim’s Bridge & Hamblen Island

The combo is one of the best hikes and outdoor Cape Cod adventures. Located in Wellfleet, it’s one of the most photographed places in the whole region! Established in 1783, its original name was “The New Bridge.” It spans Duck Creek to connect Hamblen Island to the mainland and central village of Wellfleet. “Uncle Tim” is Timothy E. Daniels, a retail shop owner in the 1800s whose shop was right across from the bridge. Walk the bridge to the island and enjoy outdoor activities like beaches, walking trails, Wellfleet Harbor, and more. The bridge is on the State Historic Register.


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. 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.

An Indoor Home Base for Outdoor Cape Cod Fun

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, as well as many other outdoor adventure spots around the Cape.

We’re also close to many area attractions, sites, tours, shopping, dining, and activities the area has to offer. Choose from two-bedroom units for your smaller group or family, all the way up to a ten-bedroom estate for a Cape Cod outdoor adventure getaway with all your loved ones. Prepare a delicious home-cooked meal of the day’s catch, in the fully equipped kitchen. Afterward, spread out in an open living space for a movie or to recount the day’s adventures. Enjoy the view from the private balcony or patio or spend some time near the pool at select rentals.

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