In summer, the northern reach of the East Coast has much to offer anyone who loves to go cruising. If you’re looking for an idyllic stretch of water to explore over the course of a week or more, head for the shores near the state line separating New Hampshire and Maine. From there, you can take in big views from the helm, visit historic sites and salty towns, tie up and take a hike, or drop the hook in some of the most beautiful anchorages anywhere in the world.
Start in New Castle, New Hampshire—the gateway to a Gulf of Maine adventure. There, you can spend a night at Great Common Island, which is just south of the Portsmouth Naval Shipyard. (It’s awe-inspiring to watch a new naval destroyer leave the yard on the Piscataqua River as it heads out for sea trials.) You can get your provisions in order and then head up to Kittery Point, just across the state border, the southernmost point in Maine.
A nice offshore side trip is a run through the Isles of Shoals. You can pick up a mooring at picturesque Gosport Harbor, which divides the cluster of islands. At one side is Star Island in New Hampshire; at the other, Smuttynose in Maine. Star Island was one of the busiest fishing ports on the East Coast in the 1600s; later it was home to a grand hotel, The Oceanic. Today, cruisers come here to get close to nature from kayaks, trails and rocking chairs that line the wood porch of the island’s restaurant. If a classic Maine sunset is on your bucket list, you can check that box here.
To get to Kittery Point, you enter Portsmouth Harbor, passing Whaleback Lighthouse and Wood Island Life Saving Station to starboard and Fort Constitution to port. Here, you get a sense of what the area was like in the past, when former captains, officers and British merchants had large homes on the Maine side. The tightly packed cluster of smaller homes on the New Hampshire side were for the deckhands and working class.
Maine’s southern coast belies the image that most people have of it. There are no rocky outcroppings traversed by puffins. Instead, from Kittery to Cape Elizabeth, the coast is home to some of the state’s most popular beaches, including Old Orchard. Scarborough is another popular location, with miles of tidal pools and marshy canals that kayakers enjoy plying when the tide is right. Hearty surfers can be seen off some of the beaches. They don thick wetsuits to ride the waves because the average water temperature of the ocean in the summer is 56 degrees; keep that in mind before taking a dip.
Popular attractions in the area include the Cape Neddick Lighthouse, also known as Nubble light, and Mount Agamenticus, which sits just a few miles inland and served as a landmark for mariners when the Popham Colony was founded at the mouth of the Kennebec River in 1607. Then there’s Biddeford Pool, off Sac Bay, where Capt. Richard Vines spent the winter of 1616 to prove that the Maine climate wasn’t too severe. He called it Winter Harbor and returned to establish a permanent settlement on the Saco River in 1623, the same year that Kittery was founded.
In Casco Bay, you’ll approach the working harbor of Portland, the largest city in the state. Here, streets are lined with galleries and shops and there’s great dining at dozens of award-winning restaurants. Portland may have been the childhood home of Henry Wadsworth Longfellow, but it’s a foodie’s town today. History buffs can check out the Spring Point Ledge Light that was built in 1808 to help guide ships through the main channel into Portland Harbor. Then there’s Fort Gorges, which was constructed in the 1860s and stored submarine mines during World War II. Because of its position, this landmark can be reached by boats of many sizes.
The scale of Casco Bay is relatively small—the distance from Cape Elizabeth to Cape Small is less than 20 miles, and in clear weather you can see the Portland skyline from Harpswell Neck. And yet Casco Bay is home to many islands, including Little and Great Diamond, Long, Cliff and Chebeague. They were once known as the Calendar Islands because there was one for each month of the year. Peaks Island has more than 1,000 year-round residents and is a good day trip. Transient slips and moorings are available and there’s a general store and restaurant.
At the north corner of Casco Bay, tidal Harraseeket River leads to a well-protected harbor in the village of South Freeport. Boats have been built on the Harraseeket River since the first settlers arrived. One of the most famous, Dash, was constructed at the Porter Yard at the beginning of the War of 1812. Ships weighing up to 400 tons were built at what is now Brewer’s South Freeport Marine. The town might be best known as home to the L.L. Bean store but there’s another good reason to spend an afternoon here: lobster. Tie on a plastic bib at Harraseeket Lunch & Lobster, a mom-and-pop eatery on the dock that serves up boiled “bugs” and fried seafood.
When you’re ready to transition to Maine’s more traditional, rocky coastline, head for Harpswell. Safe Harbor Great Island is in this beautiful and more rugged part of the state, in protected Orrs Cove. It has transient slips, moorings, a fuel dock, and an on-site restaurant.
For a day trip, run just six miles from the marina to Snow Island at the head of Quahog Bay. It’s a good spot for those who want to throttle back in a place that’s not overrun with tourists. Look for seals, watch for birds and maybe take a quick dip in the warmer water here. There’s also an oyster farm—slurp Snow Island oysters right off the shell and you’ll fund local environmental programs.
From Harpswell, you can run to many classic cruising destinations. Just up the coast are Boothbay, Damariscotta, Waldoboro and Rockland. This area is the heart of Mid-Coast Maine and stretches north to the Downeast region that begins at Ellsworth and Bar Harbor.
Spend some time in Rockland, a large commercial port that’s easy to enter and offers plenty of space for anchoring. Need spare parts or supplies for your boat? Hamilton Marine has a store right in town near the waterfront. Rockland is abuzz with shops, a theater, restaurants, two art museums and more. Cape Air provides service to Boston’s Logan Airport from the Knox County Regional Airport in nearby Owls Head and the Concord Trailways bus line stops at the ferry terminal, in the event you want to plan for a crew change.
Rockland is the end point for this cruising itinerary, but if you have more time and curiosity, it could be the starting point for an extended adventure into Penobscot Bay and some of the most pristine cruising grounds on the Atlantic Coast. Experienced cruisers say you can spend a week on Penobscot Bay and barely scratch its surface. But that’s another story. The point is, for new and experienced cruisers alike, this corner of the country has much to offer.
This article was originally published in the July 2024 issue.
