5 Beautiful Stops On The Perfect Coastal Maine Road Trip

“Vacationland” is the name given to the state of Maine. Most vacationers to the Northeastern state gravitate to its beautiful, rocky coast when they plan their visit, stringing together several small towns to create the perfect road trip.

But it wasn’t just as a vacation destination that Maine garnered its fame. The Maine coast mesmerized painters like Andrew Wyeth, Winslow Homer, and Edward Hopper. Their paintings depict a mix of a steadfast, bucolic lifestyle with the harshness of seafaring.

Of the many beautiful spots along Maine’s coast, I’ve selected ones starting from the north along popular Route 1 and heading south to portray the breadth of the state’s natural and historical attractions.

1. Monhegan Island 

Mystical Monhegan Island has been the vacation home of the Wyeth family since the late 1950s. Reachable only by boat, and for most visitors only by mailboat, Monhegan has no paved roads and no cars. In the evening, there are no lights. Covering less than 1 square mile in area, Monhegan is a special place where artists, fishermen, and visitors have come for what we now call social distancing.

You can’t get seafood any fresher than what you’ll find on the island. Lobster and clams are brought to your picnic table on the sand, just steps from the ocean where they were plucked. You’d best “capture the Maine spirit,” as they say, and order an ice-cold Moxie to wash it all down. An acquired taste, Moxie is the local soft drink favorite likened by many to a mix of Dr. Pepper and cough syrup. I love it.

Monhegan Island accommodations are about as quaint as they come. There’s an inn with rocking chairs on the porch, a couple of rooming houses, and not much more. Island artists live in weathered shingle dwellings scattered on the island. 

If you’re looking for air conditioning, free Wi-Fi, and turndown service, you’ve come to the wrong place. You could visit Monhegan as a day trip only, but, for the full experience, disconnecting and booking a room to listen to the sounds of silence in the evening is better than any kind of meditation I’ve tried.

Pro Tips: The hills and hiking trails along the coast can be quite taxing. If you’re up for it, the reward is Maine’s famed coastal views and a lighthouse and museum with maritime art. For a less challenging walk, you can sit on the sloping lawn in front of The Island Inn and take in the harbor with its lobster boats, bobbing buoys, and maybe even some jumping fish. To reach the island, park your car in Port Clyde, a short drive off Route 1 or Route 295 (use your GPS), and check in at the souvenir shop for your “ferry” ticket.

2. MidCoast: Camden, Rockland, And Owl’s Head 

The area known as the MidCoast offers a taste of easygoing coastal Maine along Penobscot Bay. Art galleries and shops, bed and breakfasts, and waterside charm appeal to visitors looking to enjoy harbor views and a lobster “in the rough.” Both Rockport and Camden have working harbors — guaranteeing fresh seafood daily — and make for some stunning photos.

Plan to spend a day of varied activities in this area. Hike in Camden Hills State Park or get a dose of indoor culture at three notable museums. The Farnsworth Art Museum in Rockland showcases the work of the Wyeth family. Steps away, the Center for Maine Contemporary Art is a striking building filled with current-day oeuvres by Maine residents. Owl’s Head has a museum with a different type of appeal, the Owl’s Head Transportation Museum. The museum’s bi-planes can sometimes be seen flying over the harbor. 

Overnight on a Maine windjammer to explore the bay and the local islands, or stay in a charming bed and breakfast on the shore. Whatever you do, make sure you have a lobster: many consider this to be “lobster central.”

Pro Tip: On this 200^th anniversary of the birth of acclaimed landscape architect Frederick Law Olmsted (of Central Park fame), note the small town park in Camden, another of his firm’s design gems. 

3. Portland And Cape Elizabeth

I’d be remiss if I didn’t encourage you to spend some time in Portland. Portland is a beautiful, historic Maine city with a lively small-town vibe. Architecture ranges from Federal-style buildings to Victorian mansions, with restaurants and bars housed in traditional buildings or on the docks. 

Since parking is extremely difficult in the city, you might have to resolve yourself to a drive-through to see the Old Port, cruise the shopping area with its cobblestones and brick sidewalks, and gaze at the tonier side of the city along the Casco Bay-facing Eastern Promenade and the Western Promenade where Victorian residences stand in multi-color glory. 

If you can park, head to Congress Square to the Portland Museum of Art, a repository of paintings by international and Maine-connected artists including Wyeth, Hopper, and Homer. For dinner, choose from one of this foodie city’s many lauded restaurants like Street and Co., Scales, or Fore Street, touted as among the best U.S. eateries by Food and Wine.

Across the bridge, Cape Elizabeth seems worlds apart from busy Portland. There are only a few restaurants and shops, but your main reason to stay here is for an essentially self-contained Maine holiday experience and access to the headlands and water views from Two Lights State Park and the adjacent Lobster Shack. 

Check in to the Inn by the Sea, one of Maine’s premier resorts, and sign out one of their bikes to see the iconic lighthouses. Revive after your exertion (the roads are hilly) with a swim at the inn’s beach or with an outdoor spa treatment before enjoying a cocktail and s’mores around the fire pit.

Pro Tips: Don’t be dismayed when you see the line at the Lobster Shack — it moves quicker than you might think. Order a lobster roll, fried clams, and onion rings — all Maine favorites — and finish with another New England treat, a Whoopie pie, a chocolate cake-like concoction with a cream center. If you’re a pet lover, the Inn by the Sea has an endearing pet adoption program: you can test out a pup for an afternoon walk. If you fall in love, you have a new friend to take home.

4. The Kennebunks: Kennebunkport And Kennebunk 

The two towns comprising the Kennebunks are all about the Maine seafaring lifestyle. Side-by-side along the shores of several rivers, the towns overlap in some ways but have distinct personalities in others. You can easily combine both in a day or even a few hours of exploring.

The home base for shipbuilding and seafaring, Kennebunk boasts a main street lined with stately homes originally built for sea captains. There you’ll find Federal-style buildings along with frilly and even gothic-looking Victorian homes, many converted into inns for today’s visitors. There’s a patrician feel to the town which blurs with Kennebunkport’s combination seaside and souvenir-shop vibe.

The Clam Shack, a takeout landmark on the bridge separating Kennebunk’s Lower Village and Kennebunkport’s Dock Square, repeatedly wins the award for having Maine’s best lobster roll. Unadulterated lobster, with no unseemly add-ins like tarragon or Old Bay Seasoning, that’s what the Clam Shack’s lobster roll is all about. You decide whether you want it with butter, or with mayonnaise — or go for it and have both. Different from other lobster rolls you might have had even in Maine, the mayo is not already mixed in and celery is nowhere in sight. The flavor is pure, the lobster is warm, and the briny-sweet flavor is at its best. If you prefer a sit-down experience, Nunan’s Lobster Hut in nearby Cape Porpoise offers indoor and outdoor table service with a lobster bake experience of lobster in the shell, steamers, and corn on the cob.

The Kennebunks invite you to dip your toes into Maine’s notoriously chilly water. Beautiful Goose Rocks Beach in Kennebunkport, uncrowded due to limited sidewalk parking, is a lovely spot for exploring Maine’s fascinating tidal pools. If you’re as enchanted as I was here, you’ll want to stay at the Tides Beach Club, an atmospheric inn set directly across the street. Sit on the inn’s front porch and rock for a while as you sip a cosmopolitan and watch the sun go down.

Pro Tip: For a glimpse of American history, follow the road out to Ocean Avenue towards Walker’s Point, the site of the “compound” where former President George H.W. Bush summered with his family. Drive by and take a photo — the Secret Service will probably not let you get very close.

5. Ogunquit, Perkins Cove, And The Marginal Way 

South of the Kennebunks lies traffic-snarled Ogunquit, a magnet for art lovers and beach fans thanks to its many lodgings and cultural opportunities. There are plenty of shops to keep you busy, or you might want to see a show at one of the country’s last summer stock theaters, the Ogunquit Playhouse. The line-up features original and touring musicals for both adults and children and runs through December. The stunning Ogunquit Museum of American Art is a small art museum with a sculpture park with 18 gardens.

If parking in Ogunquit proper is an impossibility, drive south to one of Maine’s coastal gems, Perkins Cove. Fortunately, there are parking lots here to help ease the pain. And that’s good for you, too, for herein lies a quintessential Maine eatery, Barnacle Billy’s, your go-to for a lobster and Maine’s state dessert, blueberry pie made with Maine’s tiny wild berries. This is also where you can sample Maine ice cream in typical New England flavors like butter pecan, rum raisin, peppermint stick, and black raspberry. Use the local vernacular and ask for “jimmies” on top.

Walk down the cove, stopping to admire jewelry made from sea glass, t-shirts with witty sayings, and some serious art. Then turn north to enter the Marginal Way, a 1.25-mile paved cliff walk above the rocky Maine coast. The flower-adorned path has some gently sloping areas as it winds its way towards the heart of Ogunquit, with beautiful homes on the left and crashing waves to the right. If you’re feeling a bit adventurous, you can do a bit of rock scrambling, taking note of slippery areas from the salt water. For a rest, there are 39 thoughtfully placed benches along the route.

Pro Tip: Allow enough time to do the return trip to retrieve your parked car. You’ll get a different perspective as your head south this time.