11 Best Things to Do in Cape Cod All Year Long

Where Beach Life Meets New England Charm

The hook-shaped peninsula of Cape Cod delivers way more than just pristine beaches and lobster rolls. This Massachusetts gem packs serious vacation potential with its mix of outdoor activities, historical sites, and small-town vibes. From lighthouse-hopping to whale watching, here’s your ultimate guide to experiencing the best of the Cape.

Cycle the Cape Cod Rail Trail

Starting in South Dennis and winding through six towns, this 25-mile paved path offers the perfect blend of exercise and sightseeing.

The trail connects to beaches like Coast Guard Beach, used by cyclists, joggers, and walkers, with local bike shops like Barbara’s Bikes offering daily rentals starting at $25. You’ll pedal past cranberry bogs, salt marshes, and charming village centers.

Stop at Nickerson State Park for a quick dip or grab an ice cream at Sweet Izzy’s in Brewster. This year, stay tuned for new extensions of the Rail Trail which will expand access through additional scenic areas, including new beach access points.

Hit the Perfect Beach Timing

To dodge the summer crowds, visit between mid-September and mid-October. The water’s still warm (around 65°F), hotel rates drop significantly, and parking spots exist.

The beaches maintain their beauty without the chaos of peak season. Early mornings (before 9 AM) and late afternoons (after 4 PM) offer the most serene experiences.

Plus, September brings the Cape Cod Food Truck Festival at the Barnstable County Fairgrounds (September 14-15) and Wellfleet OysterFest (October 19-20, 2025), adding extra entertainment without the seasonal surge.

Explore the Cape Cod National Seashore

President Kennedy established this protected shoreline in 1961, which stretches for 40 miles along the Outer Cape.

Explore six pristine beaches, including Race Point, where you can occasionally spot North Atlantic right whales from shore, and Marconi Beach, where 40-foot sand cliffs endure the battering of Atlantic waves.

Fun fact: Seashore is a UNESCO Biosphere Reserve with diverse habitats such as salt marshes, dunes, and tidal flats.

The Seashore crisscrosses with hiking trails like the 1.6-mile Atlantic White Cedar Swamp Trail in Wellfleet, offering a rare glimpse of an ancient forest ecosystem. Join the ranger-led interpretive walks to learn about the peninsula’s geology.

Chase Lighthouse Views

Cape Cod boasts 14 historic lighthouses. The candy-cane striped Nauset Light in Eastham appeared in Cape Cod Potato Chips advertisements.

Tour it on Sundays and Wednesdays from May through October. Highland Light in Truro stands as the Cape’s oldest and tallest lighthouse at 66 feet, offering breathtaking 360-degree views of the Atlantic.

Chatham Light provides dramatic views of the ever-changing Chatham Bar sandbar, where seals gather by the hundreds, and dramatic light bathes their iconic silhouettes amidst Truro’s pine-topped dunes.

Savor Fresh Seafood

The bounty of the sea arrives daily at Cape Cod’s restaurants and markets. Try local specialties like creamy quahog clam chowder or the freshly shucked Wellfleet oysters.

For a truly authentic experience, you can purchase seafood directly from the fishing boats at Chatham Fish Pier between 1-3 PM, where fishermen unload their daily catch of cod, haddock, and bluefin tuna.

Witness Whale Watching Wonders

From April through October, the waters off Cape Cod become a feeding ground for humpback, finback, and minke whales.

Whale watching cruises take you to Stellwagen Bank National Marine Sanctuary, where these magnificent creatures breach and feed just 7 miles offshore.

Learn about unique behaviors like bubble-net feeding technique pioneered by a humpback named Salt in the 1980s. The average tour lasts 3-4 hours, and most companies guarantee sightings, offering a free return trip if no whales are spotted.

Remember to bring sunscreen and a light jacket, as temperatures on the water can be 10-15 degrees cooler than on land, especially during morning excursions.

Step Back in Time in Provincetown

At the Cape’s northernmost tip, P-town (as locals call it), you’ll witness Commercial Street buzzing with art galleries, boutiques, and restaurants housed in 19th-century buildings.

Did you know? East End Cultural District houses the highest concentration of working artists in the country.

The Provincetown Art Association and Museum showcases works influenced by the Cape’s special light, including paintings by Charles Hawthorne, who founded the first art colony here in 1899.

History buffs shouldn’t miss the 252-foot Pilgrim Monument, commemorating the Mayflower’s first landing in 1620, where 116 steps and 60 ramps lead to views stretching to Boston on clear days.

The town’s accepting atmosphere makes everyone feel welcome, while Art’s Dune Tours provides sunset excursions through the fragile dune ecosystem that inspired writers from Eugene O’Neill to Norman Mailer.

Discover Island Day Trips

A short ferry ride from Hyannis takes you to Martha’s Vineyard (45 minutes on the high-speed Steamship Authority ferry) or Nantucket. Starting in 2025, faster and more eco-friendly ferries will be introduced for island travel.

On Nantucket, cobblestone streets lined with whaling captains’ homes and boutique shops. Drop by the Whaling Museum on Broad Street to catch a 46-foot skeleton of a sperm whale and the 1849 Fresnel lens from Sankaty Head Lighthouse.

Martha’s Vineyard charms visitors with its colorful gingerbread cottages in Oak Bluffs and dramatic clay cliffs at Aquinnah.

Kayak Through Serene Marshlands

Animal enthusiasts, kayak through marshy swamps for amazing wildlife encounters. The salt marshes and tidal flats in Cape Cod are some of the best places to spot migratory birds, such as the endangered piping plover.

Guided tours through Nauset Marsh in Eastham reveal hidden channels teeming with snowy egrets, great blue herons, and fiddler crabs. Kayaks are rented from numerous outfitters, including Cape Kayaking in Orleans for $45 per half-day.

Immerse Yourself in Arts and Culture

The Cape’s natural beauty has inspired generations of artists, resulting in a thriving cultural scene. The Cape Cod Museum of Art in Dennis houses an impressive collection of works by regional artists. Public art installations dot the landscape, with the Heritage Museums & Gardens in Sandwich displaying 14 monumental works.

Wander Through Charming Town Centers

Each of Cape Cod’s 15 towns possesses its unique personality and attractions. Sandwich, the oldest town founded in 1639, features well-preserved colonial architecture and a working grist mill. Wellfleet’s town center revolves around an old-fashioned town square with weekly farmers’ markets.

Pro tip: Talk to the local shopkeepers for the secret garden behind Truro’s Public Library. It’s a hidden gem.