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5-Day Driving Trip from Boston, Massachusetts to the Maine Coast

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Day 1: Boston to Portland, Maine

Morning: Depart from Boston and enjoy a scenic drive north along I-95. Stop at Kittery Outlets for some shopping and a quick brunch.

Afternoon: Arrive in Portland and explore the Old Port District with its cobblestone streets, boutiques, and art galleries. Visit the Portland Head Light, one of the most photographed lighthouses in Maine.

Evening: Dine at one of Portland's renowned seafood restaurants and take a leisurely stroll along the Eastern Promenade to enjoy sunset views over Casco Bay.

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Day 2: Portland to Camden

Morning: Drive up the coast stopping at Freeport for a visit to the L.L. Bean Flagship Store and local shops. Grab breakfast at a cozy café before continuing north.

Afternoon: Arrive in Camden and explore the charming harbor town. Take a hike up to Mount Battie in Camden Hills State Park for panoramic views of Penobscot Bay.

Evening: Enjoy a waterfront dinner at a local eatery then stroll through the town’s quaint streets to take in the local shops and art scene.

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Day 3: Camden to Bar Harbor

Morning: Depart Camden early and drive toward Bar Harbor with a stop at the charming town of Rockland to visit the Farnsworth Art Museum.

Afternoon: Arrive in Bar Harbor, check into your accommodation, and spend the afternoon exploring Acadia National Park. Drive the Park Loop Road and visit Sand Beach and Thunder Hole.

Evening: Have dinner in downtown Bar Harbor and enjoy a peaceful waterfront walk under the stars.

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Day 4: Exploring Acadia National Park

Morning: Start early with a sunrise hike to the summit of Cadillac Mountain, the highest point on the U.S. East Coast. Enjoy breathtaking panoramic views as the sun rises.

Afternoon: Continue exploring Acadia with a visit to the Jordan Pond House for lunch and a leisurely stroll around Jordan Pond. Optionally, bike the carriage roads for a scenic experience.

Evening: Relax with a quiet dinner in Bar Harbor, perhaps sampling some fresh lobster, and visit some local shops and galleries.

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Day 5: Bar Harbor to Boston

Morning: Enjoy a leisurely breakfast in Bar Harbor before departing south. Stop by the town of Wiscasset to explore its historic downtown and have lunch.

Afternoon: Continue the drive back to Boston, taking break stops in quaint coastal towns like Portsmouth, New Hampshire.

Evening: Arrive in Boston by early evening, concluding your memorable Maine coast road trip with plenty of photographs and experiences to cherish.

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Time and Cost Estimates

  • Kittery Outlets: 1.5 hours, Free to browse, cost varies for shopping
  • Portland Head Light: 1 hour, Free
  • L.L. Bean Flagship Store: 1 hour, Free
  • Mount Battie Hike: 2 hours, Free
  • Farnsworth Art Museum: 2 hours, Approx. $15 per person
  • Acadia National Park: Full day, $35 per vehicle for park access
  • Jordan Pond House Lunch: 1.5 hours, $20-$35 per person
  • Fuel for total trip (~550 miles): Approx. $80-$100 depending on vehicle

Total estimated cost: $150 - $200 per person (excluding lodging and shopping)

Tips

If you want to extend your trip, consider adding a day to explore more of Acadia National Park or take a boat tour around the islands of Casco Bay. For a shorter trip, focus on Portland and Camden with a day trip to Acadia, skipping the longer drive to Bar Harbor. Booking accommodations early is recommended during peak summer months, and be sure to pack layers as coastal Maine can be cool in the evenings even in summer.

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