Portland & The Maine Coast 🦞
"Lighthouses, lobster rolls, and rugged Atlantic shorelines."
Start in the foodie-hub of Portland, then drive North along Route 1 toward Acadia or South toward Kennebunkport. It offers a classic American road trip vibe with rocky beaches and charming coastal towns.
A classic New England road trip blending Portland's world-class culinary scene with the rugged beauty of the Midcoast and Acadia's rocky shores.
Day-by-day itinerary
Day 1 · Historic Old Port and Coastal Views
Morning — Arrive in Portland. Start with a walk through the historic Old Port, grabbing a 'Potato Donut' from The Holy Donut. Explore the cobblestone streets and maritime boutiques.
Afternoon — Walk the Eastern Promenade for panoramic views of Casco Bay; visit the Portland Observatory, the last maritime signal station in the US.
Evening — Head to the Old Port district for dinner. Enjoy fresh oysters at Eventide Oyster Co. and a cocktail at the Portland Hunt + Alpine Club.
💡 The Old Port is very walkable, but parking is difficult; use garages over meters for long stays.
Day 2 · Lighthouses and Local Beaches
Morning — Take a 15-minute drive to Cape Elizabeth to visit Portland Head Light, Maine's oldest lighthouse. Walk the trails in Fort Williams Park.
Afternoon — Relax at Willard Beach in South Portland, a favorite local spot. Afterward, visit the Portland Museum of Art to see the Winslow Homer collection.
Evening — Grab a flight of local craft beers at Shipyard Brewing or Allagash, then dine on the waterfront at Scales for high-end seafood.
💡 Try the 'Bite Into Maine' food truck at Fort Williams Park for a lobster roll with a view.
Day 3 · The Road North to Midcoast Maine
Morning — Pick up a rental car and drive north to Freeport (20 mins). Stop for a classic blueberry muffin at a local bakery.
Afternoon — Browse the L.L. Bean Flagship Store (open 24/7) and the surrounding outlet shops in the village.
Evening — Drive up to Rockland/Camden area. Have a relaxed dinner at a local pub like the Sea Dog Brewing Co. in Camden.
💡 Freeport can get crowded; if you want a quieter nature break nearby, head to Wolfe's Neck Woods State Park.
Day 4 · Sails and Summits in Camden
Morning — Explore Camden Harbor. Walk along the marina and watch the historic windjammers. Consider a 2-hour morning sail on an authentic schooner.
Afternoon — Hike or drive to the summit of Mount Battie in Camden Hills State Park for a view the locals call 'where the mountains meet the sea.'
Evening — Enjoy a farm-to-table dinner at Natalie's at Camden Harbour Inn or a more casual meal at Long Grain for excellent Thai-inspired local fare.
💡 Schooner trips usually require booking at least a day in advance during peak summer months.
Day 5 · Adventure in Acadia National Park
Morning — Drive 1.5 hours north to Mount Desert Island. Enter Acadia National Park and walk the Jordan Pond Path for iconic views of "The Bubbles."
Afternoon — Visit Sand Beach, the only sandy beach in the park, then drive the Park Loop Road, stopping at Thunder Hole.
Evening — Return to Bar Harbor for a traditional Maine Lobster Bake at a rustic spot like Abel’s Lobster.
💡 To see the sunrise from Cadillac Mountain, you must secure a vehicle reservation weeks in advance.
Day 6 · The Scenic Route 1 Return
Morning — Enjoy a quiet breakfast in Bar Harbor, then begin the scenic drive back down Route 1 toward Portland.
Afternoon — Stop in the charming village of Rockport or Wiscasset. Join the line at Red's Eats in Wiscasset if you want the most famous lobster roll in the state.
Evening — Return to Portland for a final celebratory dinner at Fore Street before your late departure or final night stay.
💡 Route 1 is much slower but more scenic than I-295; leave early if you want to stop in multiple towns.