7 Best Places to Visit Between Boston and Maine

A journey from Boston to Maine is one of New England’s most scenic and rewarding road trips. Stretching along the Atlantic coastline, this route offers charming towns, coastal views, and historic sites that make every mile worth the drive. Whether you’re traveling solo, as a couple, or with family, these seven must-visit destinations between Boston and Maine will make your trip unforgettable.

1. Salem, Massachusetts – A Town of History and Mystery

Just 25 miles north of Boston, Salem is a fascinating blend of colonial history and seaside charm. Famous for the 1692 witch trials, Salem now draws visitors with its rich heritage and lively cultural scene. Explore the Salem Witch Museum, tour The House of the Seven Gables, or enjoy a walk along the Derby Wharf overlooking the harbor.

The cobblestone streets, boutique shops, and festive atmosphere—especially in October—make Salem a unique first stop on your journey.

2. Gloucester, Massachusetts – The Spirit of the Sea

About an hour from Boston, Gloucester is America’s oldest working seaport and a symbol of New England’s maritime legacy. The Fishermen’s Memorial Statue honors generations of local sailors, while the Cape Ann Museum showcases the town’s artistic and nautical history.

Relax on Good Harbor Beach, savor freshly caught seafood, or take a thrilling whale-watching tour. Gloucester offers both adventure and tranquility, all framed by stunning ocean views.

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3. Rockport, Massachusetts – Artistic Beauty by the Ocean

A short drive from Gloucester brings you to Rockport, a charming seaside village beloved by artists and travelers alike. Its most iconic landmark, Motif No. 1, is said to be the most painted building in America.

Walk down Bearskin Neck, where colorful shops and galleries line the waterfront. For panoramic ocean vistas, visit Halibut Point State Park—a peaceful escape perfect for photographers and nature lovers.

4. Newburyport, Massachusetts – A Harbor Town with Heart

As you continue north, Newburyport offers a perfect blend of maritime history and modern comfort. The town’s beautifully preserved red-brick architecture, boutique stores, and riverside restaurants make it a delightful stop.

Spend an afternoon at Plum Island Beach, a tranquil stretch of sand ideal for sunbathing or birdwatching. Or visit Waterfront Park for scenic walks and family picnics. Newburyport’s small-town charm and warm hospitality make it one of the highlights of the coastal route.

5. Portsmouth, New Hampshire – History and Harbor Views

Crossing into New Hampshire, Portsmouth combines a rich colonial past with a modern, artsy energy. The Strawbery Banke Museum lets you step back in time, exploring restored homes and interactive exhibits spanning 400 years.

Downtown Portsmouth features a lively mix of shops, galleries, and restaurants, many housed in historic buildings. Dine along Bow Street overlooking the harbor, or catch a live performance at The Music Hall. Its vibrant culture and walkable streets make it a favorite among New England travelers.

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6. Ogunquit, Maine – A Beautiful Place by the Sea

Welcome to Maine! The coastal town of Ogunquit, meaning “beautiful place by the sea,” truly lives up to its name. Known for its pristine beaches and artistic flair, it’s one of Maine’s most picturesque spots.

Stroll the Marginal Way, a stunning coastal path that winds along rocky cliffs with endless ocean views. Enjoy the soft sands of Ogunquit Beach, or take in a show at the historic Ogunquit Playhouse, a local landmark for performing arts.

7. Kennebunkport, Maine – Coastal Elegance and Charm

Your final stop, Kennebunkport, is a quintessential Maine seaside retreat. The town’s harbor is lined with boats, boutiques, and seafood restaurants serving the freshest lobster rolls in New England.

Explore Dock Square, filled with art galleries and cozy cafés, or drive along Ocean Avenue for breathtaking coastal scenery. The Seashore Trolley Museum, the world’s oldest and largest of its kind, adds a touch of nostalgia to this elegant destination. Kennebunkport perfectly captures the relaxed yet refined spirit of the Maine coast.

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Making the Journey Comfortable

If you’re planning this coastal road trip but prefer not to drive yourself, a boston taxi service can make the experience far more comfortable and flexible. Traveling with a professional driver means you can sit back, relax, and enjoy the views without worrying about parking, navigation, or traffic. It’s a convenient way to explore multiple destinations at your own pace.

Similarly, for travelers heading south after exploring New England, a boston to new york taxi service is another excellent option—offering private, stress-free travel between two of the East Coast’s most vibrant cities.

Final Thoughts

A trip from Boston to Maine isn’t just about the destination—it’s about the scenic journey through New England’s heart and soul. From Salem’s historic streets and Rockport’s artistic lanes to Ogunquit’s beaches and Kennebunkport’s coastal elegance, each stop tells its own story.

Take your time to explore, stop often, and immerse yourself in the beauty and character that make this route one of America’s most memorable drives. Whether you’re traveling for relaxation, culture, or adventure, these seven places between Boston and Maine promise experiences you’ll cherish long after the journey ends.