Harpswell

No matter what time of day it is, you can smell the sea salt and hear the boats hum in certain parts of Harpswell.

The eastern portion of the small Maine town of Harpswell is an enclave of islands, each with its own distinctive personality. The tight-knit Bailey Island convenes around the lobster industry and its general store, Orr’s Island has a special protected cove where the wind can’t get in and Great Island is where you’ll find tons of lobstermen and old fishing weirs.

“You drive down and you’ll see fishermen in fishing gear, and places to buy lobster and buy fish,” says Curt Fish, owner of Sharon Drake Real Estate in nearby Bath. “You have to go pretty far up the coast before you see lots of fishermen in one place.”

Throughout the islands, houses include see everything from multifamily properties for around $200,000 to shingle-style shorefront homes with deepwater docks for $3 million. There are 1970s bungalows for $330,000, ten-year-old contemporary ranch-style houses for $750,000, modern contemporary houses with board and batten exteriors for $400,000 and contemporary brick houses with cathedral ceilings for $1.6 million. Harpswell is a mostly year-round community, says Fish, but about 30% of residents are so-called “summer folk.”

One of the highlights of these idyllic keys is Cliff Trail, a hiking area along Strawberry Creek in Great Island. The trail includes a 150-ft. cliff with breathtaking views of the Long Reach waterway. The creekside portion of the hike was updated in 2021 to include a smooth wide path, accessible for people who either use mobility devices or have limited mobility. Devil’s Back Trail Area, named for a trail that runs along the “spine” of the devil’s back, goes through a mixed forest that includes a handful of apple trees. If you take the trail down to Gun Point Cove, you can climb out to the rocks for a picnic during low tide.

Orr’s Island and Bailey Island are vibrant communities with a Nantucket or Martha’s Vineyard sort of vibe, Fish says. Here, residential areas closely packed with cottages are close to a handful of beaches and conservation areas, like the rocky Houghton Graves Park. There are also plenty of places in Harpswell where you can go kayaking or learn how to sail. “You really feel like you’re out in open ocean,” Fish says. “You can always smell salt water, and you can always hear a boat going this way or out.”

Tucked away at the northern tip of Orr’s Island is Long Cove, a secluded, dead quiet waterway. Because it opens to the north, wind can’t get inside, and as a result the water here is warm. Neighbors can come here to get a reprieve from the otherwise windy key, or to escape during a hurricane.

Harpswell is part of Maine School Administrative District 75, which has about 2,400 students between the towns of Bowdoinham, Harpswell, Bowdoin and Topsham. About 125 children in kindergarten through fifth grade attend Harpswell Community School.

When it’s time to eat, Bailey Island General Store has a mix of convenience items plus freshly made pizza and lobster rolls. Right next to the historic Cribstone Bridge connecting Bailey and Orr’s is Cook’s Lobster & Ale House. You can have your lobster whole here, or in stew form, packed into a grilled cheese or fried into wontons. You can also order it submerged in a big bowl of macaroni and cheese.

Even though these are islands, it’s not terribly inconvenient to get to the highway. It’s a short drive to both Route 1 and I-295, which will take you down to Portland and its international jetport.

Aquaculture and boating are deeply engrained into this community. If you move here, you can join in the fun and come sail away.

Written By

Laura Finaldi

Photography Contributed By

Jeff Tippett

Video By

Tyler Cataldo