10 Ways to Make the Most of Your Cape Cod Vacation

Perfect for anyone headed to Massachusetts’ famed coastal getaway, these travel ideas are tried, true, and terrific.

By Yankee Editors

Apr 24 2023

CCC_Marconi_Paul Scharff

Marconi Beach, Cape Cod, MA

Photo Credit : Paul Scharff

By Megan Johnson; sponsored by the Cape Cod Chamber of Commerce

Whether you cross into Cape Cod via the bridges or by hopping off a ferry or a flight, you’ll immediately be immersed in a vacation destination that can cater to every kind of traveler, from adventurous types to laid-back loungers. Yet no matter your itinerary for visiting this endlessly scenic peninsula on the Atlantic Ocean, filled with beautiful beaches and bustling coastal towns, there are certain experiences here that are guaranteed to take your trip to the next level — and deliver the kinds of memories that will keep you coming back for more. You could call them a bucket list, but in truth, they’re just the beginning of the bottomless possibilities that await on your Cape Cod getaway.

1. Make a P-Town Pilgrimage

Dedicated in 1910, the Pilgrim Monument is the tallest all-granite structure in the U.S. — and the view from the top can’t be beat.
Photo Credit : Hawk Visuals

Before the Pilgrims landed in Plymouth, they spent five weeks exploring the ocean-swept outermost tip of Cape Cod, an area of rolling dunes and wide-open vistas that would eventually become Provincetown. First established as a whaling and fishing village, it transformed through the years into a welcoming enclave for immigrants, artists, and the LGBTQ+ community. Get a bird’s-eye view of today’s Provincetown and the surrounding seascape from the top of the 252-foot-tall Pilgrim Monument, then dive into the downtown scene to explore a unique fusion of New England village and arts-and-culture oasis. Stroll the galleries and museums; take in a comedy, cabaret, or drag show; and enjoy the taste of coastal living at one of the many locally owned cafés and restaurants (going strong for almost half a century, seafood favorite The Lobster Pot is a can’t-miss).

2. Enjoy Local Flavor by the Pint or Glass

If you’re treasure hunting for Cape-brewed beer, check out the many tempting options at Hog Island Beer Co., whose name honors a rumored Orleans haunt of the infamous pirate Captain Kidd.
Photo Credit : Ben Nugent

With their ever-growing variety of distilleries, breweries, and wineries, Cape Cod and its island neighbors, Nantucket and Martha’s Vineyard, always have something tasty on tap — and often with a gorgeous view, to boot. In North Truro, for instance, Truro Vineyards offers a ruggedly beautiful backdrop for enjoying a glass of this chill winery’s rosé or a smooth-sipping whiskey from their new distillery, South Hollow Spirits. Over at Hog Island Beer Co. in Orleans, meanwhile, you can kick back at a picnic table on the lawn with a cold Nauset Haze or White Shark Wheat. And in Falmouth, Bad Martha Farmer’s Brewery invites beer lovers to relax in the taproom or outdoor patio while noshing on a charcuterie platter or artisan pizza (for those visiting the Vineyard, there is a second Bad Martha location in Edgartown).

3. Discover the Beauty of the Dunes

Venturing into the Peaked Hill Bars Historic District near Provincetown lets hikers catch a glimpse of decades-old artists’ shacks amid an untamed landscape of coastal sand dunes.
Photo Credit : Jon Miksis

To the human eye, the famed sand dunes of Cape Cod seem to roll like endless golden waves across the landscape. If you’d like to dive into their lovely expanse, one of the best ways is by booking an adventure-filled journey with Art’s Dune Tours: Founded in 1946 in Provincetown and still run by the same family, this outfit gives visitors a rare off-road look at the Cape Cod National Seashore — and no one else offers such a colorful, historical, and ecologically sensitive experience of this fragile ecosystem. Prefer to explore at your own pace? The Provincetown Dune Shacks Trail winds through the Peaked Hill Bars Historic District, where you’ll spot the rustic seaside shacks that have offered creative refuge to iconic writers and artists over the years.

4. Gear Up for a Bike Adventure

As the longest paved bike trail in the state of Massachusetts, the Cape Cod Rail Trail gives riders plenty of opportunities to make scenic detours along the way, including visiting Marconi Beach in Wellfleet.
Photo Credit : Paul Scharff

Whether you’re an off-road type or an easy-going cruiser, one word sums up the experience of biking on Cape Cod: smooth. Among the 100-plus miles of bike trails that crisscross the peninsula, the most iconic route might be the paved 25-mile Cape Cod Rail Trail, which stretches all the way from South Yarmouth to Wellfleet on the Outer Cape. But many other gems await to be discovered, including the 7.25-mile Province Lands Trail, a ride that offers an unforgettable look at the wild dunes near Provincetown. For off-pavement fun, head to a spot like the West Barnstable Conservation Area, whose 1,200 acres are laced with 21 miles of singletrack that twist, climb, and plunge through pristine conservation land.

5. Explore the Cape Cod National Seashore

Forty miles of coastline including six gorgeous beaches make it easy to find your perfect patch of sand in the Cape Cod National Seashore.
Photo Credit : Paul Scharff

Created on August 7, 1961, with JFK’s presidential pen stroke, the 44,000-acre national park known as the Cape Cod National Seashore gave everyone access to one of the most treasured stretches of coastline in the East; today it draws more than 4 million visitors annually with its endless opportunities for recreation. Kettle ponds and ocean beaches invite sunbathing and swimming, while those looking to stretch their legs can choose from 15-minute strolls, hour-plus walks, and even a three-to-five-hour trek on the Great Island Trail, considered one of the best hikes in the state. And wildlife fans will get their fill, too, as more than 400 species of animals make their home in this protected landscape.

6. Catch a Show on a Timeless Stage

With its rich tradition of attracting top actors, the nearly century-old Cape Playhouse in Dennis was famously once described as “the place where Broadway goes to summer” by The New York Times.
Photo Credit : Paul Scharff

First opened in 1927 in a former Unitarian meetinghouse, the Cape Playhouse in Dennis has seen countless stars of Broadway and Hollywood perform their magic on its stage, including Henry Fonda, Bernadette Peters, and Julie Andrews. Now revered as the country’s oldest professional summer theater, the Playhouse still delights audiences of all ages with its annual mix of comedies, musicals, and dramas. Among the shows this season, you can tap your toes to the music of Fats Waller with Ain’t Misbehavin’ (June 7-17), relive the golden era of Broadway musicals with Lerner & Loewe’s Camelot (Aug. 16-26), and delve into the world of Sir Arthur Conan Doyle with Baskerville: A Sherlock Holmes Mystery (Aug. 30-Sep. 9).

7. Immerse Yourself in Blooming Wonders

For anyone enchanted by hydrangeas’ lush puffballs of color — like the beautiful specimens in this garden in Dennis — the 10-day extravaganza of the Cape Cod Hydrangea Festival is an essential summer event.
Photo Credit : Greta Georgieva

When July rolls around, the signature pinks, whites, and blues of hydrangeas seem to blanket Cape Cod, whose soil and climate are a boon to this flowering beauty. Little wonder that the Cape Cod Hydrangea Festival (July 7-16, 2023) is celebrated across the Cape for a full 10 days each July, giving attendees the chance to take private tours of gardens overflowing with the iconic blooms, as well as attend lectures and workshops by leading horticulturalists and artists. As a bonus, this flower fete coincides with the annual Hydrangea Festival at Heritage Museums & Gardens in Sandwich, whose Cape Cod Hydrangea Display Garden offers a showcase of about 155 species and cultivars, including many “historic” cultivars that are not commonly found.

8. Cheer on Future Baseball Stars

Bringing generations together at local ballfields from June to August, the Cape Cod Baseball League is just the ticket for a family night out.
Photo Credit : Paul Scharff

As summer twilight descends across the Cape, the glow of stadium lights marks the fields where teams from 10 towns play in the Cape Cod Baseball League, the country’s elite summer league for college players. They are the chosen ones, the best of the best, each athlete on the cusp of a dream to one day play under the lights at a major league park. And the drama is real: More than 300 current and former MLB players spent at least one summer on the Cape, including Hall of Famers Jeff Bagwell and Carlton Fisk. The games are free—and you are close enough to the action to see the dream play out on the young athletes’ faces.

9. Embark on a Whale of a Ride

Cape Cod offers some of the best whale watching in the world, thanks to its proximity to the Stellwagen Bank National Marine Sanctuary.
Photo Credit : Paul Scharff

An impressive delegation of the world’s whale population heads to the waters off Cape Cod each year to frolic and feed from spring till autumn in the Stellwagen Bank National Marine Sanctuary, an 842-square-mile federally protected area. This is prime time for anyone hoping to glimpse a humpback, minke whale, or other gentle giant — and luckily you can turn that hope into reality thanks to Cape Cod’s whale watching scene, which includes the veteran tour operators Hyannis Whale Watcher Cruises in Barnstable, Dolphin Fleet in Provincetown, and Captain John Boats in Provincetown and Plymouth. Just grab your sunscreen, climb aboard, and settle in for a trip guaranteed to be educational, entertaining, and — above all — exciting.

10. Bask in a Cape Cod Sunset

Perched at the tip of the Cape Cod peninsula, Race Point gives visitors a wide-open vista to the west that’s perfect for sunset viewing.
Photo Credit : Mark Fleming

Among its “85 Best Things to Do in New England,” Yankee magazine touted the beauty of watching the sun go down at Race Point in Provincetown: “Dunes at your back, seals bobbing in the waves, sun melting into the horizon … look around. Everyone’s in awe, no matter how many times they’ve stood here before.” But that particular strip of the Cape Cod National Seashore is far from the only place for appointment viewing when the sky turns to gold, pink, and lavender. From Old Silver Beach in North Falmouth to Skaket Beach in Orleans, there are plenty of inviting spots to put down a blanket and watch the show, maybe with a soft-serve cone in your hand. Or, for a different perspective, take to the water on a sunset kayak tour like the one offered at RideAway Adventures, and enjoy the sensation of gently bobbing on water filled with the reflected majesty of the setting sun.

This post is funded by the Massachusetts Office of Travel & Tourism.

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