Coastal Maine Road Trip: A Lobster Roll Pilgrimage
I first visited coastal Maine as a preteen. Of all my childhood trips, it’s one of the few that stuck. Maybe it was the rocky shoreline, maybe the salty breeze, or maybe it was the lobster, fresh out of the trap and onto my plate. Decades later, it was time to go back and see if Maine still tasted as good as I remembered. Spoiler: it does.
We planned eight days in mid-September, that sweet shoulder-season window when everything’s open but the summer crush has faded. Days reached the high 70s to low 80s, mornings were crisp, and the skies behaved like they had a postcard quota to meet. Our route: two nights in Kennebunkport, a foodie stretch in Portland, then Bar Harbor and Acadia National Park for the grand finale.
Kennebunkport: Sea Captains, Shoreline, and a Perfect First Night
We checked into the Kennebunkport Captains Collection, settling in the Nathaniel Lord Mansion (1812) with its high ceilings, creaky floors, and “did a sea captain just pass by?” vibes. Breakfast in the main house was a lovely spread: juices, pastries, fruit with yogurt, granola, and a hot dish, served in the dining room or out on the porch.
First evening: patio seats at Batson River Brewing & Distilling. Craft cocktails, truffle fries, lobster bisque, and duck-fat cornbread (extra points for creativity) made for a relaxed, happy start.
The next day we followed Ocean Avenue from Dock Square toward Walker’s Point, the Bush family’s summer compound perched on a rugged outcrop where waves pound the shore and a flag stands watch. To one side, historic sea captains’ homes turned boutique inns; to the other, Atlantic swells working the granite. We stepped into St. Ann’s by-the-Sea Episcopal Church, a stone chapel built in 1887 right on the rocks, before later borrowing bikes to retrace the route at a breezier pace, stopping at Blowing Cave for views of Sandy Cove and the Bush estate.
Lunch came from The Clam Shack. Their famous lobster roll wasn’t our favorite of the trip (don’t worry, redemption comes later), but the fried scallops were excellent and the warm wild-blueberry hand pie was divine.
Few things feel more Maine than biting into a lobster roll at a roadside shack with the water right beside you.
After a quick Dock Square browse and a restorative nap, we grabbed two bar seats at Old Vines and shared small plates: truffle fingerlings, blue-cheese short-rib toasts, and crisp pork belly, paired with cocktails. It was our favorite dinner in town and exactly my idea of a perfect meal: graze, sip, repeat.
Portland: Lighthouse Views, Working Harbor, and A+ Eating
On the way into Portland, we detoured to Portland Head Light atFort Williams Park. Commissioned in 1791, it’s Maine’s oldest lighthouse and best admired from a little seaside overlook where cliffs, surf, and white tower align. Around the park we wandered past the early-1900s batteries Keyes and Blair and the ivy-clad shell of the 1858 Goddard Mansion, which leans just enough toward “haunting” to be atmospheric rather than spooky.
Lunch at Bite into Maine sealed it: our trip’s top lobster roll. Toasted bun, generous chunks of sweet lobster, warm butter; the kind of simple perfection that rewires your memory. We followed it with a slice of wild-blueberry pie and ice cream from Pie-Oh-My!, eaten with a view of the water because that’s how dessert is meant to be.
Downtown, we checked into The Press Hotel (once the headquarters of the Portland Press Herald), where typewriters, letterpress blocks, and a walk-everywhere Old Port location made us instantly happy. Parking, however, required strategy (and a valet splurge).
Evening one was a greatest-hits lineup: cocktails and Hunt popcorn at Hunt & Alpine (my Bonecrusher was the standout).
Oysters, tuna crudo, and a brown-butter lobster roll at Eventide (our #2 roll of the trip), and, for science, a whoopie pie. I respect the Maine devotion, but I’m still team blueberry pie.
Morning began at Holy Donut, famous for its potato-based donuts that somehow manage to be both dense and tender. We tried four flavors—chocolate sea salt, maple bacon, triple berry, and vanilla glaze—with maple bacon the hands-down winner. The potato gives them a moist, almost cake-like texture that feels more indulgent than sugary, the kind of breakfast that sets you up happily for miles of walking.
Lobstering with the Pros
We’re not tour people. We like to wander on our own. But some experiences belong to the experts, and lobstering is one of them. After research, Lucky Catch Cruises ticked every box: owner-operated, small group, hands-on, captained by a real lobsterman on his own boat.
Our 90-minute trip with Captain Tom (forty years on the water) threaded Portland Harbor and Casco Bay. He’s funny, easygoing, and wildly knowledgeable. All fifteen passengers hauled traps, measured, re-baited with herring, and banded claws. We even idled off Portland Head Light for the best lighthouse view of the day. It was one of our favorite Portland experiences: educational, memorable, and pure Maine.
We walked the Eastern Promenade afterward—harbor views, dogs living their best lives at the beach, and the biggest private yacht we’ve ever seen. By then, it had been a scandalous few hours since our last lobster, so we fixed that with lunch at Gilbert's Chowder House. Their “super” chowder doubles the catch—clams, shrimp, haddock, and lobster in a creamy broth that tastes like the ocean decided to show off. We paired it with fried whole-belly clams, briny and tender, unless you look too closely at the belly. The Hubs did. He regrets it. I chose blissful non-inspection and kept eating.
We peeked at Victoria Mansion (tours didn’t align). Consolation prize: stumbling on Becky’s Diner, the home of the “best whoopie pie in Portland,” and testing yet another whoopie pie in the name of research. Better, but still too sweet for me. Some people adore them; I’ll never yuck their yum.
The Hubs redeemed the day with a brilliant pick: Blyth & Burrows for cocktails. He declared the Ship Captain Crew his favorite drink of the trip. Dinner at DuckFat followed: duck-confit poutine and a soppressata grilled cheese that made me wish I had space for the famous doughnut holes and a milkshake. Next time.
Bar Harbor & Acadia: Tides, Trails, and a Sunset Send-Off
En route to Bar Harbor we detoured to the Coastal Maine Botanical Garden in Boothbay. Beyond the gorgeous plantings, five towering wooden trolls are hidden through the woods—part treasure hunt, part environmental tale. We found them all, felt like kids, and left grinning.
We tried to continue to Owls Head State Park and McLoon's Lobster Shack, but lost cell service in the “fingers of Maine” and had to abort. Lunch salvation appeared at The Shuck Station in Newcastle: a garlic-butter-kissed lobster roll (our #3 of the trip) and excellent fried haddock, eaten at picnic tables in the sun.
In Bar Harbor we checked into the waterfront Bar Harbor Inn, a luxury property on Frenchman Bay that overlooks the harbor and the Porcupine Islands, right in the heart of downtown. We lucked out with a balcony facing the water—perfect for morning coffee and tide (or people)-watching.
With the tide out, we walked across the exposed bar to Bar Island (it’s only passable about 90 minutes on either side of low tide), hiked the quiet loop, and headed back before the ocean swallowed the path.
After tide walks and harbor strolls, we realized we’d been dangerously long without seafood. Dinner that night righted us at Havana, where charred octopus, seafood paella, and mojitos reminded us why coastal dining spoils you for anywhere else. On the way back, we stopped at Mount Desert Island Ice Cream for a scoop that absolutely lived up to the buzz.
Morning at 2 Cats Bar Harbor was solid if unremarkable; the farmer’s breakfast did its job.
Then we headed into Acadia. The park, founded in 1916 as the first national park east of the Mississippi, protects a dramatic meeting of mountains and sea. We parked at Sand Beach and set out along Ocean Path, a two-mile trail tracing the rugged shoreline to Otter Point and back (about four miles total). Granite cliffs rose on one side, surf on the other, the whole coastline smelled of pine needles steeped in salt air.
At Thunder Hole, where waves slam into a narrow cavern to send spray stories high, we caught only a gurgle instead of the famous boom—but it was easy to imagine how thunderous it could be on a stormy day. Boulder Beach lived up to its name, a tumble of rounded stones smoothed by centuries of waves, each one clicking softly as the tide rolled in and out. At Otter Cliff, one of the tallest headlands on the Atlantic coast, we stopped to watch climbers rappel straight down its pink granite face to the sea below. The combination of forest, ocean, and sheer stone felt like Acadia showing off all its best sides in a single walk.
Back in town, we grabbed a popover with blueberry jam and a chowder from The Stadium, then took them to a bench in Agamont Park with a harbor view. A partial closure on the Shore Path cut our stroll short, but it was still a peaceful loop along the water.
We napped, then settled into the garden patio at Project Social for cocktails and small plates: beef skewers and duck tacos (hits), a rich lobster crepe (I loved it), and five-spice pork belly (his favorite, a touch strong for me). Twinkle lights, warm evening, happy us.
Our last morning began at Cafe This Way, where a blueberry pancake rewired my understanding of breakfast; crisp edges, fluffy center, blueberry to the core. It jumped to my “best ever” list. The Hubs liked his chocolate-chip pancake more than his egg sandwich, so we both won.
Fueled up, we drove back into Acadia to walk the 3.3-mile loop around Jordan Pond.
Carved by glaciers more than 10,000 years ago, the pond is one of the clearest in Maine, with water so pristine the park forbids swimming to protect its ecosystem. On the east side, a narrow boardwalk snakes across wetlands; on the west, the trail turns rocky, with stretches that feel like nature’s own staircase. All along the way, The Bubbles, two rounded mountains rising side-by-side, mirror perfectly in the glassy surface of the pond. We spotted beaver-gnawed stumps, listened to the hush of wind through pine, and took our time soaking it in.
Halfway around, we detoured up to Jordan Pond House, where popovers have been a tradition since the 1890s. Ours arrived hot and hollow, steam rising as we split them open, served with jam and blueberry ice cream. Sitting on a rock overlooking the pond with the popovers in hand felt like joining a century-old club of hikers, presidents, and day-trippers who’ve ended their Acadia walk the same way.
For sunset, we drove up Cadillac Mountain (vehicle reservation required in season). Layers and a blanket were non-negotiable. We snagged a spot by the west overlook, watched the temperature dip, and waited. At first a cloud bank muted the sun. Then we watched the sky shift from gold to fiery pink to indigo. When the sun finally dropped, the whole crowd clapped. It was that kind of sunset; one you’ll remember for years.
Late dinner at Tap & Barrel Tavern: truffle-parmesan fries, a juicy burger, and short-rib toast was cozy and unfussy; just what we wanted on our last night. It also marked our first lobster-free meal in a week. I could already feel the withdrawal.
Departure morning, we returned to The Stadium to grab coffee and breakfast sandwiches for the drive. A little dry, but they did the job. As we crossed back onto the highway, I missed Maine already.
Coastal Maine gave me exactly what it did when I was twelve: wonder, salt air on my lips, and more lobster than one person strictly needs (not that I complained). I don’t think we’ll retire there; the winters are real, but it’s one of those places that gets under your skin: a little wild, a little weathered, and a lot delicious. There are more trails to wander, more sunsets to catch, and at least a few more lobster rolls with my name on them.
I hope this inspires you to travel, to eat, and to join me as I continue sharing my journey through seven continents and infinite foods.
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If You Go – Quick Itinerary
Day 1: Kennebunkport - Kennebunkport Captains Collection
Batson River Brewing & Distilling **waitlist available
Day 2: Kennebunkport - Kennebunkport Captains Collection
Old Vines **takes reservation
Day 3: Kennebunkport to Portland
Pie-Oh-My! food truck
Hunt & Aline and Eventide
Day 4: Portland - The Press Hotel
Day 5: Portland to Bar Harbor
Havana **takes reservation
Day 6: Acadia National Park - Bar Harbor Inn
The Stadium and Agamont Park
Project Social **waitlist available
Day 7: Acadia National Park - Bar Harbor Inn
Jordan Pond House **takes reservation
Cadillac Mountain **timed reservation required
Day 7: Home
**I would highly recommend that you make reservations in advance when available. I always book scheduled activities and typically make dinner reservations in advance. I’ve indicated with a parenthetical any restaurants that take reservations.