The Ultimate Road Trip Along Maine’s Stunning Coastline
Here’s a mind-blowing fact about Maine: the Pine Tree State boasts a longer coastline than California! That’s right—when you tally up every bay, cove, and tidal inlet, Maine’s shoreline stretches over 3,478 miles, edging out California by about 50 miles. Scattered along this vast coastal tapestry are 65 historic lighthouses, charming fishing harbors, and some of the most picturesque seaside towns in the country.
I went on the ultimate Maine adventure, sailing aboard a 150-year-old schooner, weaving in and out of Maine’s islands. It’s a truly unique experience and one I can’t recommend enough! After our week on a rustic sailboat, we set out to explore the coast of Maine so I wanted to share my itinerary with you.
Whether you’re planning a romantic getaway, a solo escape, or a family vacation, this curated road trip along Maine’s famous Lobster Trail will immerse you in the best places to stay, eat, and explore. Get ready to pack your bib and dive into some of the freshest lobster and seafood around!
Day 1: Arrival & Kennebunkport
Fly into Boston and pick up your rental car. The drive to Kennebunkport takes about two hours, but you’ll want to slow down and savor every mile of this iconic Maine coastline. Stop often for snapshots of quaint harbors, rocky cliffs, and the signature red-roofed lobster shacks. You’ll pass the glassy Mystic River and the leafy suburbs of the North Shore before skimming the tidal flats of Newburyport’s Parker River Wildlife Refuge. Crossing into New Hampshire, the highway arches over the Piscataqua River with postcard views of Portsmouth’s red‑brick waterfront and tugboats. Minutes later you hit Maine, where dense pine forests, roadside lobster shacks, and antique barns pepper the short stretch to Exit 25; detour onto U.S. Route 1 for glimpses of Ogunquit’s sandy coves and the marshy inlets of Wells Reserve. The final miles wind through salt‑air–scented wetlands until the road delivers you into Kennebunkport’s storybook harbor lined with weather‑worn clapboard homes, bobbing lobster boats, and the iconic white spire of South Congregational Church.
Check in at the Nonantum Resort, a quintessential New England-style hotel set right on a tranquil fishing cove. The resort offers two distinct experiences: the historic Carriage House Inn with cozy, classic rooms, and the contemporary Portside Lodge, featuring spacious balconies overlooking the harbor.
Just a short stroll from the resort, Mabel’s Lobster Claw offers a cozy, old-fashioned atmosphere—think grandmother’s dining room with a nautical twist. Order the iconic Maine feast with New England clam chowder, steamed native clams, and a whole fresh lobster to kick off your trip right.
Day 2: Lobster Fishing & Lighthouses — Learn & Explore
Start your day with a fascinating Rugosa Lobster Tour departing from Nonantum’s docks. Captains Bob and Phil will take you aboard their lobster boat for a two-hour hands-on adventure, explaining the history, sustainability efforts, and hard work behind Maine’s lobster industry. It’s educational, fun, and an authentic coastal experience.
Next, drive north to Portland, stopping at Cape Elizabeth to visit Maine’s oldest and most photographed lighthouse, Portland Head Light. The scenic ocean views and crashing waves make this a perfect photo stop.
For lunch, head to DiMillo’s On the Water, a unique seafood restaurant housed on a historic car ferry docked in Portland Harbor. Enjoy fresh local dishes with sweeping water views.
Continue on to Freeport, the outdoor enthusiast’s shopping paradise and home to the legendary L.L. Bean flagship store.
Settle into the Harraseeket Inn, nestled on Freeport’s charming main street. This welcoming inn offers spacious rooms, many with cozy fireplaces, perfect for those cool coastal evenings. Don’t miss their award-winning brunch or afternoon tea by the fire.
For dinner, try the inn’s own Porter Kitchen & Bar and be sure to sample all of the local seafood. End your evening around the patio fire pit with a cocktail under the stars.
Day 3: Shopping, Hiking & Seafaring Adventures
Freeport’s Village Station is a shopper’s dream, packed with outlet stores featuring outdoor gear, fashion, and local artisan crafts. Beyond shopping, nature beckons at nearby Wolfe’s Neck Woods State Park, where gentle trails wind through forest and shoreline, ideal for a refreshing hike.
After a morning of exploration, drive on to Rockland, a coastal town famous for its vibrant arts scene and maritime heritage. Stop in Boothbay Harbor along the way to join a whale-watching tour—one of Maine’s most thrilling wildlife encounters.
In Rockland, stay at the historic Berry Manor Inn, a beautifully restored Victorian home offering charming rooms close to the bustling harbor and shops.
Dine at Rockland Café, a homey, comfortable little cafe and try to seafood lasagne.
Day 4: Arts, Culture & Bar Harbor Relaxation
Rockland surprises visitors with two must-see cultural gems: the Farnsworth Art Museum, dedicated to American and Maine artists, and the Center for Maine Contemporary Art. Families will appreciate the hands-on fun at the Coastal Children’s Museum.
From Rockland, it’s about a two-hour scenic drive to Bar Harbor, the gateway to Acadia National Park.
Book a stay at the elegant Bar Harbor Inn, where waterfront views, a heated outdoor pool, and a spa invite you to relax after your adventures.
Just steps from the inn, enjoy a casual meal at Side Street Cafe. Their lobster mac ‘n’ cheese is a local favorite—comfort food with a coastal twist.
Day 5: Acadia National Park
Spend your final day exploring the crown jewel of Maine’s coast, Acadia National Park. Visit the Abbe Museum in Bar Harbor to learn about Maine’s Native American heritage or explore the Mount Desert Oceanarium for family-friendly marine exhibits.
Don’t miss a drive up Cadillac Mountain for sweeping panoramic views of the Atlantic—Maine’s highest point and one of the first places in the U.S. to see the sunrise.
From Bar Harbor, you can either fly out of nearby Bangor or retrace your route back to Boston. If time allows, retracing your steps along the coast offers more opportunities to revisit your favorite spots.
Travel Tips & Season Notes
- Best time to visit: Late spring through early fall for mild weather, open attractions, and vibrant coastal scenery. Many coastal businesses close in winter.
- Packing: Layers are key—cool mornings, ocean breezes, and warm afternoons call for versatile clothing.
- Local culture: Respect lobster fishermen and the environment—Maine takes great pride in sustainability.
- Don’t forget: Bring your appetite and your camera; Maine’s coast delivers on both!
This road trip promises fresh seafood, breathtaking views, charming inns, and memorable adventures that showcase the rugged beauty and warm hospitality of coastal Maine. Whether you’re savoring lobster by a roaring fire or watching the sunset over a historic lighthouse, you’ll fall hard for this spectacular slice of the Northeast.