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A road trip from Boston to Cape Cod is one of the most scenic and rewarding journeys in Massachusetts. Covering just over 70 miles, the drive can be done in under two hours without traffic, but the true magic lies in taking your time to explore the charming towns, coastal views, and cultural landmarks along the way. From historic sites to seaside escapes, this route offers a blend of New England history and coastal beauty that makes it unforgettable.
Here are 8 must-visit places to include on your Boston to Cape Cod trip.
Located just south of Boston, Quincy is often the first stop on the way to Cape Cod. Known as the “City of Presidents,” it’s the birthplace of two U.S. presidents—John Adams and John Quincy Adams. Visitors can explore the Adams National Historical Park, which includes family homes, gardens, and a historic library.
Quincy is also famous for its waterfront, offering spots like Marina Bay with restaurants overlooking the harbor. If you want to start your road trip with a taste of New England seafood, Quincy’s clam shacks and waterfront eateries won’t disappoint.
For those who love nature, a quick detour to Blue Hills Reservation offers hiking trails and panoramic views. Located in Milton, this 7,000-acre state park provides over 100 miles of trails, including a climb up Great Blue Hill, where you’ll be rewarded with sweeping vistas of Boston’s skyline. It’s a refreshing way to enjoy the outdoors before heading further toward Cape Cod.
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No Boston to Cape Cod trip is complete without stopping in Plymouth, one of the most historically significant towns in the U.S. Known as “America’s Hometown,” Plymouth is where the Pilgrims landed in 1620. The iconic Plymouth Rock, Mayflower II (a replica of the ship), and Plimoth Patuxet Museums provide a window into early colonial life.
Beyond history, Plymouth has a lively harborfront filled with shops, restaurants, and whale-watching tours. It’s a perfect spot to stretch your legs, grab a meal, and immerse yourself in history.
As you cross the Sagamore Bridge into Cape Cod, one of the first towns you’ll encounter is Sandwich, the oldest town on the Cape. Founded in 1637, Sandwich combines history with natural beauty.
Highlights include the Heritage Museums & Gardens, showcasing art, cars, and lush gardens, as well as the Sandwich Glass Museum, which reflects the town’s glassmaking heritage. For a peaceful walk, the Boardwalk at Sandwich Town Beach offers a serene coastal experience.
Barnstable is the largest town on Cape Cod and offers plenty to see and do. History lovers can visit the Coast Guard Heritage Museum or stroll along Main Street in Hyannis, which is filled with shops, restaurants, and galleries.
Hyannis is also home to the John F. Kennedy Hyannis Museum, a must-visit for those interested in the Kennedy family’s deep ties to Cape Cod. Ferry services to Nantucket and Martha’s Vineyard also depart from Hyannis, making it a great jumping-off point for further exploration.
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The town of Dennis is beloved for its combination of natural beauty and cultural charm. On the north side, you’ll find calm Cape Cod Bay beaches like Mayflower Beach, while the south side offers warmer waters at Nantucket Sound beaches.
For evening entertainment, the Cape Playhouse in Dennis is one of the oldest professional summer theaters in the U.S., hosting performances since 1927. Whether you’re after sunbathing or stage shows, Dennis delivers.
Further east along the Cape lies Chatham, a postcard-perfect town known for its iconic lighthouse, quaint downtown, and rich maritime history. Chatham Lighthouse Beach is one of the most scenic beaches in New England, and the Chatham Lighthouse itself is still an active Coast Guard station.
The town center has boutique shops, art galleries, and restaurants serving fresh seafood. Don’t miss the Chatham Fish Pier, where you can watch fishing boats unload their catch—a slice of authentic Cape Cod life.
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At the very tip of Cape Cod is Provincetown, often referred to as “P-town.” Known for its vibrant arts scene, welcoming community, and stunning natural surroundings, Provincetown is a destination in itself.
History buffs can visit the Pilgrim Monument and Provincetown Museum, which commemorates the Pilgrims’ first landing in Provincetown before moving on to Plymouth. Nature enthusiasts will love exploring the Cape Cod National Seashore, with its dramatic sand dunes and pristine beaches.
Provincetown is also famous for its lively nightlife, art galleries, and whale-watching tours. Ending your Boston to Cape Cod trip here ensures a memorable finish.
A road trip from Boston to Cape Cod is more than just a drive—it’s a journey through history, culture, and breathtaking coastal scenery. From Quincy’s presidential past to Provincetown’s artistic energy, each stop along the route has something unique to offer.
Whether you’re after history, beaches, food, or adventure, these 8 must-visit places will make your Boston to Cape Cod trip one you’ll always remember.
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