Harpswell, Maine - Listen to the Sea Tell Its Stories as You Savor the Flavor - Lobster, Clams, Oysters, Oh My

The scent of salt and seaweed permeated the breeze off Casco Bay as we rolled into Henry Allen’s Seafood on Lookout Point Road in Harpswell, Maine. The place is nestled into a tiny cove off Middle Bay, the nearby rocky ledges and protruding points at falling tide revealing golden brown swaths of sugar kelp, patches of Irish moss, and rockweed.

“This is why I wanted to come here,” I told Maria. “The views, the smells, the seafood.”

Indeed, the little seafood retail barn and wharf, the adjoining Morse’s food truck, and the lobster boats bobbing in the water a hundred yards from shore all combine to create an intimate space, one seemingly sculpted into the coastline by a visionary poet with calloused hands, perhaps earned by decades of pulling traps from the briny deep.

Perched just above Henry Allen’s on Lookout Point is the Harpswell Inn, a magnificent home that was originally a 1700s shipbuilders’ home and carriage house. The carriage house is now converted into two suites. Several rooms in the main house are set up for guests. The place was getting ready for a wedding when we arrived. Crashing the reception briefly crossed my mind, but my shorts and and flip flops probably would have tipped someone off that I wasn't on anyone's guest list.

Savor the flavors and sights of Harpswell

The mission to Henry Allen's was to buy lobsters for the evening dinner. Instead of a motel or a B&B accommodation, though, our destination was a nearby, beautiful, pet-friendly AirBnB home with a wraparound deck affording commanding views of the bay and magnificent sunsets. My sister Sally and brother-in-law Bruce were joining us for a couple of days. A long-anticipated lobster feast on the deck was in the works.

The seafood shack's lobsters were in tanks, segregated by size and shell condition. A friendly employee explained that they sold only lobsters – hard shells and soft shells (recently molted) – and rock crabs.

Now, I’ve eaten at least a thousand blue crabs, which are famous around the Chesapeake Bay. Rock crab was new to me. “All you eat are the claws and legs – not the body,” she said. “You just steam them with the lobsters. The fishermen often break off the big claws and throw the crab back. The claws grow back.”

A nice rock crab claw - sweet, delicious

“Okay, give me five 1.5-pound hard shell lobsters and one 2-pounder (for hungry, greedy me) and I’ll try two of the crabs,” I said. It was mid-July, peak tourist season on Maine’s gorgeous MidCoast, the area north of Portland that extends to Belfast. The lobsters were $8.50 a pound, about as inexpensive as anywhere – I know, because I called several places. Four of the lobsters would be eaten that night. The other two would be cooked and picked in the morning, the meat destined for homemade lobster rolls, the next day lunch.

She picked out two of the biggest crabs, then paused and added one more – a freebie, a little something extra for the rock crab virgin, I gathered. In Louisiana’s Cajun country, they would call it “lagniappe.”

“Thank you,” I said. “Enjoy,” she responded cheerfully.

As we were leaving, we scanned the menu board at Morse’s, noting it could be a good option for any meal we didn’t want to cook “at home.” A haddock sandwich might hit the spot.

The home-cooked lobster dinner, with fresh, sweet corn on the cob, baby Yukon gold potatoes and green beans, washed down with ample chardonnay wine and gin and tonics was one for the record books. And those little rock crabs – not bad, if a little sparse on the meat end.

Day 2 – A Trek to Bailey Island

Bailey Island at the terminus of the Harpswell area on Casco Bay was the day two destination. Leaving Harpswell Center you head north before turning right on Mountain Road, crossing Ewin Narrows and skirting the scenic “Cliff Trail” before getting on Route 24, Harpswell Islands Road, and traversing Orr’s Island. The road constantly winds, narrows and widens. We passed weathered shingled homes, roadside stands selling wild blueberries, and a handful of quaint to impressive bed and breakfast operations.

Then came the Cribstone Bridge—a marvel of engineering and stubborn Yankee ingenuity. Built entirely of stacked granite slabs, it flexes with the tide and spans Will’s Gut, connecting Harpswell to Bailey Island like a handshake between land and sea. This feat of civil engineering is on the National Register of Historic Places.

Mackerel Cove is about halfway across Bailey Island. It’s hard not to slam on the brakes and just stare in awe at the abject beauty and tranquility of this placid cove, loaded with colorful fishing vessels and runabouts. The Pinwheel Tuna Fishing Charters boat, the one made famous from the Wicked Tuna television series, often operates out of this cove. The Johnson Field Preserve at Mackerel Cove is a beautiful place to get out of your vehicle, take your dog for a run or a walk and just drink in the coastal Maine ambiance. The cove’s gentle waters are also an excellent launch point for kayaks, canoes, or paddle boards.

A small parking area is available. A lobster boat that was heading out of the cove reversed course when the captain saw my brother-in-law Bruce’s vehicle pull in to park. “Ya need some lobstahs? I’ve got lobstahs,” the skipper yelled toward shore. Business first.

Kids toss stones smoothed by centuries of rolling in the tide into the surf while dogs chase tennis balls in the foam. Such moments feel like they’re the ones you just need to be living in, versus being in constant photographer mode, looking for a good shot.

Bailey Island is also home to the Giant’s Stairs Trail. The walk along the craggy coastline toward the beloved rock formation affords commanding views of wide Casco Bay. It’s not just a stroll down an earthen path, it’s a meditation. Jagged rocks tumble into the Atlantic like ancient vertebrae. Waves rhythmically crash and the seagulls foraging in the exposed seaweed hop and fly along the buffet line, just outside the pounding water’s reach.

The legend is the stairs were built by a mythical giant. Besides the ever-present gulls, visitors might also see ducks or harbor seals. The Giant's Stairs trail and property is owned and maintained by the Town of Harpswell. According to the town’s website, in 1910 the 2.5-acre strip of coastal land was deeded to the Town by Captain William Henry Sinnett, a lifelong resident of Bailey Island. The narrow foot path used to be choked with poison ivy but in 2008 the Maine Conservation Corps, various Town committees and community members resurfaced, widened and stabilized the primary 700-foot path. Another 700 feet of trail runs across rocky ledges on the abutting McIntosh Lot Preserve, managed by the Harpswell Heritage Land Trust. It complements the Giant's Stairs trail and completes a loop back to the parking area.

The “stairs” appear in a narrow cut in the rocks. They begin at the waterline and rise in a terraced fashion toward the trail. It is a place where some might not want to venture too close to the edge. There are no railings or other barriers to protect you during a dangerous misstep.

The terminus of Bailey Island is fittingly called “Land’s End.” Once you dead-end at the ocean, you find a large gift shop offering souvenirs, soft drinks and snacks. It shares the point with an often-photographed, high-patina sculpture titled “A memorial to all Maine fisherman who have devoted their lives to the sea.” Victor Kahill created the bronze sculpture in 1939 for the World’s Fair in New York. Views at Land’s End aren’t much different than any of a number of vantage points around Harpswell, but a bonus is a small, pebbled beach, great for dipping your toes in the cool water. Dogs on leashes are permitted.

Dining on as much fresh seafood as possible was a key component of our Maine mission. Savor the flavors and sights of Harpswell. Satiated with lobsters the day before, the Day 2 dining plan was to find steamer clams and littlenecks (quahogs). We’d steam them, cook linguini, and make a sauce with butter, white wine, lemon and pepper. Research revealed that the best place to get these delectable morsels was in Phippsburg, one peninsula to the north, just east of the shipbuilding town of Bath. Clam Hunter Seafood, about 40 minutes away, was the destination. Good, clean clams are worth the drive. There, we ordered six pounds of clams and added two dozen Spirit Pond oysters (cocktail size) for good measure.

Maine’s oysters are vastly different from their southern cousins. Smaller, brinier, and loaded with sweet flavor, eating one is like tasting the sea. Oyster connoisseurs enjoy tastings of the offerings grown in the various rivers and coves of the MidCoast. Just like Virginia oyster aficionados can discern a James River oyster from a Potomac River oyster, so can Maine experts tell the difference between varieties from the Damariscotta River or the Basket Islands.

Maine oysters are much slower growing than their Gulf Coast counterparts, often needing up to four years to reach market size. Maine’s cold, clear waters and strong tides offer oysters abundant food. The slow growth, though, lets the oysters develop their great flavor. Even fresh oysters harvested from the cool waters in summer are delicious. They’re even better in the fall and winter when they’re storing glycogen and fattening up for the coldest months. The clams and oysters from Phippsburg – outstanding. The sunset – spectacular.

Day 3 – Lobster Boat Races

Harpswell has 216 miles of rocky coastline. Nearly every cove has lobster boats tied to mooring buoys or sidled up against wharves. Lobstering has been a Maine tradition for a long time. Lobsters were once considered trash food, something you could only feed to prisoners for a limited number of days each week. Today, they are a delicacy, a destination treat.

The lobster industry around Harpswell mostly shuts down for one day in late July for the annual lobster boat races. A summer lobster boat racing circuit starts in Boothbay and ends in Portland, drawing people from all over coastal Maine. The Harpswell races have been a summer tradition for more than 30 years.

Dozens of boats clustered in the waters off Harpswell’s Mitchell Field, separated by a lengthy straightaway where the races would take place. Each vessel is a character in its own right—some sleek and modern, others weathered but persevering, their names painted in proud, bold letters on the stern.

More than a thousand spectators and a couple hundred dogs gathered on the shore. People brought chairs and sat on the expansive beach or the grassy area above it. Hundreds more crowded onto a jetty stretching out into the water and getting you closer to the racing action. The 2025 event featured 29 races, with the boats broken down by classes, usually related to length and engine size. Food and commemorative race merchandise vendors hawked food and t-shirts. A few volunteers dressed up as lobsters. It is, in short, a spectacle, a celebration of grit, pride and saltwater heritage.

“They’re scheduled to start at 10, but they never do,” shared a volunteer who staffed a flatbed truck with speakers ready to boom race announcements to the crowd. By 11 a.m., though, they were ready to go. The sky was cloudy. A moderate wind made for choppy seas. After a seafaring, straightforward rendition of the national anthem, an invocation and thanking of sponsors, the race announcer boomed, “Alright, this first race is to determine the fastest lobster boat in Casco Bay. And they’re off.”

In the distance, you could see several boats throwing a wake and working to build speed, mostly line abreast at the start. Two boats soon pulled ahead. “Miss Ava Elaine,” piloted by Robert Johnson quickly kicked things into overdrive and left the field in the – well, not the dust - reaching speeds of 46 mph. The crowd cheered. The fastest boat of the day showed up in Race 30, the “Diesel Free-for-All,” with “Blue Eyed Girl,” skippered by Andrew Taylor clocking 50.4 mph.

Visitors to Harpswell's Mitchell Field scour the beaches for shells before the lobster boat races.

For locals, the annual races are a time of celebration. The winners get modest prizes –cash or gear – but residual profits go to the Harpswell Santa Fund. In 2024, the races generated $23,000, money that helped local families and fishermen who may have needed a little help around the holidays. It’s an example of that spirit of sharing and caring that epitomizes so many small communities.

The races aren’t just about speed; they’re about honoring tradition and legacies, generating laughter and memories. Spend time watching them and you feel like your finger is resting on the wild pulse of Maine’s working coast. In Harpswell, don’t expect congested, touristy streets like you often encounter in towns south of Portland. Once you get off the main coastal road and head down into the peninsula and islands that comprise Harpswell, expect a slow unraveling of time, a chance to cup your ears to the winds coming off the ocean and listen to the sea tell its stories. If you’re lucky, you may even join the conversation.

Harpswell – More Food and Lodging Options

Erica’s Seafood. Located on Basin Point in Harpswell, overlooking Casco Bay. Live lobsters and fresh Maine scallops (winter only). The takeout stand has ample picnic table seating and a full menu of seafood favorites plus burgers and more. It’s open through Columbus Day.

Dolphin Marina and Restaurant. Down on the tip of Basin Point, South Harpswell, at the water's edge of Pott's Harbor, this “sit-down” restaurant serves coastal fare, including lobster and other seafood dinners, plus steaks and more. Beautiful Casco Bay and island view. Specialties include fish chowder, lobster stew, and blueberry muffins.

Sundrenched.  At the entrance to Bailey Island, just across the Cribstone Bridge. Wide variety of seafood, burger, chicken options. Plus a ½-pound  Bahn Mi hotdog. Nice selection of local draft beers.

Cook’s Lobster and Ale House. Bailey Island. Established in 1955 as a small, one room lobster take-out stand, it’s now a full restaurant with large menu and superb beer/wine list, featuring 20 local craft beers.

Al fresco dining at Morse's

Morse’s Food Truck. Amazing seafood nachos. The fried haddock sandwich was huge and perfectly cooked. Exquisite onion rings.  

Harpswell Schoolhouse.  Fine dining in Harpswell – think, Lobster Bolognese and Artichoke Pancakes. Farm-to-table cuisine, emphasizing fresh, locally sourced ingredients, with everything made in-house

Bailey Island Motel.  Walking distance to the Cook’s Lobster & Ale House, the Salt Cod Cafe, Cribstone Bridge. A little longer walk to Cedar Beach, and ‘BIGS’ the Bailey Island General Store. Prices range from $99 to $249.

Log Cabin Island Inn.   Bailey Island. Each of the 9 rooms offers ocean views and beautiful sunsets. Watch the lobster boats as they work hard for their catch!

Driftwood Inn. Bailey Island. With nearly 30 individual rooms and cabins, Driftwood Inn is one of the larger lodging operations in the area. It is the oldest Inn on Bailey Island - in continuous operation for over 100 years. Three acres of land, directly on the water. About $150-$200 per night.

Sea Escape Cottage. Four cottages and two suites on Bailey Island. Expansive view of Casco Bay. Sailing cruises aboard a schooner or sloop are also available for charter. The cottages have complete kitchen equipment, including large pots for cooking lobster. In-season and off-season rates. Two-night minimum. Reduced weekly rates.

Captain’s Watch Bed & Breakfast. Perched on an elevated bluff, this 1862 home delivers expansive views over the working harbor and beyond. Listed with the National Register of Historic Places and the Harpswell Heritage Trust. The original eight-room section is Maine's "oldest known coastal hotel structure."  Five rooms available. Rates range from $155 to $185 per room, plus tax.

Jameson really loved the saltwater beaches