Kayakers will find the waters in the bay very peaceful.

Big, diverse and spread out, Harpswell isn’t really a single port. Rather, it’s at least a half dozen distinctly different destinations rolled into one, with miles of shoreline ranging from rugged granite to sandy beach, densely populated to nearly empty, easily navigable to seriously challenging. And gunkholes? They’re all over the place!

Harpswell boasts some 216 miles of shoreline comprising three bays, two sounds, a sizable estuary and five harbors. Even a trailer-boat enthusiast has scads of access options, as there are no less than ten launch ramps scattered amid the town’s three peninsulas and major islands.

Perhaps the best known of Harpswell’s “grips on the sea” is what locals call “The Neck.” This westernmost peninsula terminates conveniently at Potts Harbor, the most visited of the town’s various official ports. Many boaters make this their only stop in Harpswell, and that’s a mistake. Yes, there are two excellent restaurants and a full-service marina in the northwest corner of the harbor, as well as quiet gunkholes and the impressive “reversing falls” at the entrance to Basin Cove. But nearby Mackerel Cove, on Bailey Island, is also worth a visit, given its distinctive “village within a village” atmosphere.

Like Potts Harbor, it’s located at the end of another stretch of land that juts well out to sea, convenient to the common east-west cruising route across outer Casco Bay. Unlike Potts, however, the recreational focus here is squarely on sport fishing, a tradition that has endured for nearly 80 years.

Some sailboats at Potts Point in South Harpswell.

The Bailey Island Fishing Tournament, established in 1938 and run by the Casco Bay Tuna Club, is the oldest continually running fishing tournament on the East Coast. Formerly based in Mackerel Cove, participants now have their catch weighed and processed just a short distance up Merriconeag Sound, at Cook’s Lobster & Ale House.

Even if you miss the tournament (held the last week in July), the cove on which Cook’s is located makes a worthy side trip. Here, the world’s only cribstone bridge spans Wills Gut, which separates Bailey Island from its northern neighbor, Orrs Island. Built almost entirely of granite slabs that are stacked, Lego-like, into “cribs” of support, the bridge is now a National Historic Landmark, not to mention a nifty piece of engineering.

If the cove is too crowded for an overnight stay (as it often is), you can always drop the hook across the sound in Harpswell Harbor. This large bight also offers a rough sand beach that shows on the chart as a hooked arm at Stover’s Point. This is town-owned land, so you may see a sunbather or two enjoying the shore and salt marsh just behind the spit of sand.

If you seek even more seclusion, continue northeastward into Harpswell Sound, where the shoreline features fewer side-by-side bungalows and more forest with the occasional home here and there. In addition to the obvious gunkholes, the tide begins to accelerate here, especially in Ewin Narrows, where a bridge with 30 feet of clearance limits taller boats from enjoying the Harpswell Cove area. The tidal currents around Princes Point are downright intimidating, and often require more than just casual attention to the helm.

The historic Bailey Island Bridge, also known as the Cribstone Bridge.

The truly daring will follow the flood tide east beyond Princes Point and into Long Reach, where you may feel as if you’re on the edge of wilderness—even though Maine’s biggest city, Portland, is little more than 20 miles distant. Indeed, if your boat is short enough (under 10 feet), you can continue northward through Gurnet Strait and end up in the New Meadows River. Here begins yet another aspect of this multifaceted town, with options to the north and south—and peppered with gunkhole options along the way.

Cundys Harbor is where most mariners on the New Meadows eventually drop in. Although it can be a bit rolly in almost any weather, Cundys is home to an old-fashioned, on-the-wharf fishing village, highlighted by Watson’s General Store. Opened more than 160 years ago, Watson’s is a place to get anything you might need for a commercial or recreational fishing trip. But more than that, it’s a hangout on foggy or stormy days, a place where local fishermen swap stories (both true and gilded) while they wait for the weather to improve.

The catch of those same fishermen often finds its way to nearby Holbrook’s Grille, which locals saved from sure demise in 2009, rebuilding the pier and upgrading the landing area for commercial fishermen and hungry visitors. The fish tacos are particularly outstanding.

Continuing south between the New Meadows River and back toward Bailey Island, the entirety of Quahog Bay and a slice of eastern Casco Bay await exploration—again with numerous anchorages and islands ripe for closer scrutiny. And if that’s not enough temptation, you can head back west and north of Potts Harbor and into Middle Bay, which is yet another Harpswellian nugget of nautical nirvana. The quiet coves, warm waters (swimmably warm) and seclusion are well worth the effort.

And since all that Harpswell has to offer is impossible to cover here, you may want to check out the websites for the Harpswell Maine Business Association, the Harpswell Heritage Land Trust, and the Town of Harpswell. Or better yet, just go!