Town of Harpswell, Maine

The first of the “finger” peninsulas you’ll encounter as you head along Route 1 North in Brunswick, the town of Harpswell includes three large islands: Bailey’s, Orr’s, and Sebascodegan (or Great Island, to the locals), as well as over 200 smaller islands. The three large ones are connected to the “mainland” by bridges—one being particularly notable.

The granite base of the Cribstone Bridge (also known as the Bailey Island Bridge) was built in 1928 over Will’s Gut—an infamously turbulent avenue of tidal waters. Constructed Lincoln-log style to allow the powerful currents to pass through, this engineering marvel is the only one of its kind in existence; it was listed on the National Historic Registry of Places in 1975 and declared a Historic Civil Engineering Landmark in 1983. We don’t recommend pulling over on the bridge to try and get an up-close photo, however, as it’s quite narrow. Instead, head to Stover’s Point Preserve, where there is limited parking for their stony beach; from there you can get your prime Instagram-worthy shots.

Exploring Harpswell Maine

Stover’s Point is just one of many areas set aside for the enjoyment of all, thanks to the Harpswell Heritage Land Trust. Some of these spots are more nature-forward than others—and some are even water-access-only islands, like Crow Island Preserve or Eagle Island State Park (former home of North Pole explorer Admiral Robert Peary).

The Giant’s Stairs and McIntosh Lot Preserve Trail together create the perfect outdoor family adventure; the Stairs are actually on town property, whereas the Preserve is one of the Land Trust properties. The Giant’s Stairs trail meanders along the rocky coastline to the sound of crashing waves and offers breathtaking views of Casco Bay.

The Cliff Trail is a local favorite, and if you don’t mind heights, you’ll enjoy sweeping views from 150-foot bluffs overlooking Long Reach. Keep your eyes peeled for the fairy house villages—magical zones provided for and tended using funds bequeathed by the mysterious benefactress, Lindsey Perkins. So gather up some moss, a few shards of fallen tree bark, and an assortment of other natural detritus and settle in to build a creation of your own. It’s a uniquely calming and centering experience.

Prior to 2001, Mitchell Field belonged to the US Government and used to be a Navy fuel depot. Now, the town owns this popular spot, which offers well-tended paths, a bandstand, beach, and the Harpswell Community Garden. The garden is typically residents-only, but there’s the off-chance for an unclaimed plot once in a while for frequent visitors or seasonal folks; there is also an orchard and a play area. And be sure to visit Bowdoin College’s Coastal Studies Center on Orr’s Island to pick up a trail guide before you head out onto their nearly 4 miles of trails through a plethora of different habitats—all while enjoying gorgeous views of Harpswell Sound.

If you prefer enjoying nature via watercraft, H2Outfitters Sea Kayaking Adventures on Orr’s Island offers lessons, guided tours, and rentals for paddlers of every skill level. Rocky Coast Cruises offers 10 different boating excursions—as well as a “create your own” outing—including their most popular “Out and Around” trip, which takes passengers by points of interest like the Bailey Island Military Preserve and the Cribstone Bridge (Rocky Coast also offers a VRBO cottage that sleeps 4). Casco Bay Lines offers a narrated Bailey Island Boat Cruise as well.

Places to Stay and Eat in Harpswell, Maine

Typical to many of Maine’s coastal towns and cities, much of Harpswell’s commerce shuts down in the off-season, including restaurants and lodging; you should always verify whether a destination is seasonal or not prior to setting out on your road trip. As a matter of fact, the Log Cabin Island Inn on Bailey Island, the historic Harpswell Inn, The Driftwood Inn, and the Quahog Bay Inn are all seasonal. There are many year-round lodging options in Brunswick along Route 1, just a short ride north, however.

For sustenance, you’ll have a few more options if you’re in Harpswell in the colder months. For carefully curated wines, craft beers, treats, and gift-baskets, the Black Sheep Wine and Beer Shop is a definite go-to for one-stop, take-home snacks and beverages. They’ll even deliver one of their gourmet gift baskets to your boat or Airbnb!

The Bailey Island General Store and Eatery (or “BIGS,” to locals) is a combination café, grocery store, beer and wine shop, and mini-department store. Cook’s Lobster and Ale House, on Bailey Island, offers dine-in as well as take-away options for their impressive fresh-caught-daily menu. A newer addition to Harpswell’s year-round dining scene is the School House 1913, located at the one and only traffic light in town and offering brunch and dinner menus.

If you’re in town during the spring, summer, or fall, you’ll have far more dining options. The Dolphin Marina and Restaurant offers a full menu of fare for the seafood fanatic (their fish chowder is a must-try) and landlubber alike, all accompanied by spectacular views of Casco Bay from their waterfront location at the tip of Basin Point.

Erica’s Seafood, located just before the Dolphin Marina, is cash-and-carry, BYOB, and offers outdoor seating. The Salt Cod Café offers fresh, homemade breakfast, lunch, and baked goods, along with views of Harpswell Sound and the Cribstone Bridge. And when you are in the mood for dessert (and who isn’t?), pick up some handcrafted candy or chocolates at the Island Candy Company, or maybe a sundae is in order from Pammy’s Ice Cream Parlor.

Lastly, be sure to follow Route 24 to its end on Bailey Island. Not only will you have the opportunity to browse 2 floors of unique and affordable gifts (April-December) at the Land’s End Gift Shop, you’ll also be treated to a panoramic, breathtaking view of Jaquish Island, Halfway Rock Lighthouse, and the vast expanse of Casco Bay—no matter what time of year it is. Park in the dirt lot off to the right and either walk down onto Bailey Island Beach, or up to the grassy area in front of the shop itself, where the statue paying homage to Maine fishermen resides.

Surrounded on three sides by the majesty and mystery of the Atlantic Ocean, close your eyes, breathe in deeply—and feel Harpswell’s singular sense of seaside magic seep into your soul.

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