Written by Joe Guglielmetti

 TRIP LENGTH: 9 Nautical Miles
HIGHLIGHTS: Paddling in the open ocean, observing island life, counting seabirds and harbor seals, feeling proud for circumnavigating a formidable island in Maine
DEPART FROM: East End Beach
WATCH OUT FOR: Vessel traffic, venturi effect on winds and current in Whitehead Passage, exposure to the open ocean, swell break on the east coast of Peaks Island
RELATED TRIP DESCRIPTIONS: Fort Gorges, Whitehead Passage

Click on the image above to see the route in greater detail 


Most islands in Maine offer kayakers a plentitude of pine trees, sea roses, rocks, and birds. But it’s enjoyable to experience island life too – as in human island life. I know,  you want to paddle away from society’s spinning and get into nature. But give Peaks Island a chance!

Rounding Brackett Point on the south side of Peaks Island   (Pictured: Erin Quigley, Portland Paddle guide, Photo: Joe Guglielmetti)   

Rounding Brackett Point on the south side of Peaks Island (Pictured: Erin Quigley, Portland Paddle guide, Photo: Joe Guglielmetti)   

 Peaks is a good specimen of Maine island life, since it’s the state’s most densely populated island. Nearly eight thousand people settle in during our “hot” months (June, July, and August). That drops to about eight hundred by deep winter, and that's still a lot for a Maine island.

The island offers kayakers two sides of the Maine coast. On the outer, ocean-facing side, you'll experience a rugged, rocky coastline, crashing waves and the full range of conditions that comes with exposure to the Atlantic Ocean.  On the inner, Portland-facing side of the island, you'll encounter a generally calm and protected harbor beside a village that's packed with restaurants, ice cream shops and lots of visitors.

Getting Started

 The paddle around Peaks is less than five miles, but first you need to get there. If you leave from the East End Beach (which is usually the easiest launching site on the mainland) that will add an extra four miles to the whole trip. But there's plenty to explore on the way to the island and back.

From the East End Beach it makes sense to  start out with a crossing to Little Diamond Island. You could also easily incorporate Fort Gorges into this route, and if you've never been there you probably should, because it’s very interesting. If you’d prefer the more direct course, your bearing should be to the left of the fort, toward the small sandy beach on the west side of Little Diamond.

During this first crossing, be mindful of the tide. If it’s an ebb tide, the current moves pretty quickly because Back Cove and the Presumpscot River are pushing out a lot of water.

During the summer months, pay attention to the prevailing southwesterly, which sometimes hides until you emerge from the hill of the Eastern Promenade. If you’re unsure of the wind, observe the flag flying on the northwest side of Fort Gorges. It gives a good indication of wind direction and speed, fully extending at 10 knots.

Look out for heavy vessel traffic on this crossing. All sorts of craft travel to and from inner Casco Bay along this section of water.

What is Fort Gorges anyway? Check out our Fort Gorges trip description for more details, but the short story is that it's a granite fort that was built in 1857. But before completion, it was rendered obsolete because of the invention of heavy artillery, particularly exploding shells. The fort is now owned by the City of Portland and is open to the public (that’s you!).

The north wall of Fort Gorges (Photo: Joe Guglielmetti)

The north wall of Fort Gorges (Photo: Joe Guglielmetti)

Fort Gorges rises from Hog Island, which shoots shallow ledges like tree roots to the west, north, and east. Green cans and red nuns mark a narrow channel between Hog and Little Diamond Islands. This was the Navy’s escape channel for the anchorage of inner Casco Bay during the Second World War. Nowadays, lobster boats primarily use it. 

Watch for harbor seals in this area! They meander these waters, fishing, and peaking above the surface with puppy-like expressions, which is how they earned the nickname “seadogs”. But make sure you steer clear if they are hauled out on the ledges. Seals are easily frightened by kayakers, so you should never paddle towards them. Watch from a distance.  

Little Diamond Island Casino during an early fall storm (Photo: Joe Guglielmetti)

As you paddle around the southern tip of Little Diamond island you'll see a distinctive maroon building sitting alongside a pier. This is the Little Diamond Island Casino, originally constructed in 1905. Nowadays it’s a communal space for islanders to use, primarily when waiting for the ferry. There’s no public land on Little Diamond Island, so avoid landing here.

Circumnavigating Peaks

It's a short paddle across a busy boat channel from Little Diamond to the dense cluster of buildings and piers that mark the central harbor of Peaks Island. From there, you're set to begin the paddle around the island.

 For this trip description, we’ll circumnavigate Peaks Island counter-clockwise. As you follow the coastline of Peaks towards the west, eclectic houses perch along the hillside, and island life breathes above you. The ferry landing is a large green pier, usually bustling with activity. The ferry arrives and departs every forty five minutes or so in the summer, and it’s best to give her plenty of space if she’s around.

Just beyond the green pier, there’s a pleasant sandy beach that makes an excellent landing spot. There’s a public restroom across the parking lot above the beach, and you might already need to use it if you’ve hydrated properly. But we’ll discuss Peaks Island town a little later.

Brackett Point marks a prominent turn to the northeast, into Whitehead Passage. Round this corner and you'll see a small, bare island right in front of you that makes for a great break spot at low tide, when a sizable beach is exposed. Locals call it Catnip Island. Continuing on, you'll notice that the coastline becomes more rugged and rocky, leaving very few spots where you can easily land a kayak. There's one last break spot before you continue into the exposed waters on the other side of the island, though. The sandy spit of land that extends out to "Picnic Point" a bit further along on your left is a great spot that's open to the public.

Through Whitehead Passage

As you pass through Whitehead Passage between Torrington Point and Cushing Island, be mindful of tide, wind, and Trotts Rock (marked with a red triangle). Thanks to the elevation of Cushing Island Cliffs, and the hills on the east side of Peaks, a venturi effect often catalyzes the strength of wind and tide through White Head Passage. When a mature swell rolls in, running up against an ebb tide, wave heights can double, and smash over Trotts Rock.

Aren’t the cliffs amazing? If you look carefully, atop the cliffs you can see submarine towers that are part of Fort Levitt, a defense battery constructed during the Second World War.

Ever seen a guillemot? They are a small, black and white bird that likes to fly and swim in Whitehead Passage, and the best thing about them is how awkwardly they land; fat little bodies skipping over the surface like stones. They are members of the Auk family, which makes them closely related to Atlantic puffins.

Venturing onto the Ocean Side of the Island

A crude oil tanker passes behind Ram Island Ledge Lighthouse (Photo: Joe Guglielmetti)

A crude oil tanker passes behind Ram Island Ledge Lighthouse (Photo: Joe Guglielmetti)

As you continue along the Coast of Peaks out of Whitehead Passage, you’re in the open ocean! Austere Ram Island Ledge Lighthouse appears from behind Cushing. Completed in 1905, it’s the newest lighthouse in Maine (although it doesn’t look that way).

From this point in your journey all the way to Wharf Cove on the northeast coast of Peaks (0.5 NM), there will be no safe area to land in foul weather. You must make a solid assessment of the conditions, and your energy level, before continuing with the circumnavigation.

Considering rock-gardening on the east coast of Peaks Island (Photo: Joe Guglielmetti)

Considering rock-gardening on the east coast of Peaks Island (Photo: Joe Guglielmetti)

You now bravely paddle the east coast of Peaks, swell rolling under you, and breaking along granite ledges’ fingers. If you enjoy “rock gardening”, this stretch of Peaks is ripe for it. If when you hear someone say “rock gardening” you think of pruning a rhododendron on a hill, you may want to stay well to the right of the east coast of Peaks.

Make your way into Wharf Cove, and you enter the mouth of Hussey Sound, one of the deepest waterways on the Eastern Seaboard. As you move away from the open sea, the homes on Peaks creep closer to the shore, where there are more gentle stone beaches to explore. It’s possible to take a break in one of the three prominent coves here. Elm Tree Cove is the most difficult to land and launch within, thanks to large slippery boulders. 

Pumpkin Nob (Photo: Joe Guglielmetti)

Pumpkin Nob (Photo: Joe Guglielmetti)

Pass by Josiah’s Cove, and you approach Pumpkin Nob, a small island directly off of the northern tip of Peaks. This little place was the summer home of John Ford, the film director. Even at low tide there’s plenty of water between the Pumpkin and Peaks, and it’s an interesting passage. Look up at the houses! Talk about porches! 

Into Diamond Pass and Back to Town 

As you make your way into Diamond Pass, you’ll leave the big waters of the open sea and Hussey Sound behind, and enter the shelter of Peaks Island’s northwest coast. Across the way is Great Diamond Island, a large plot of privately owned land with one public restaurant. Above the towering rock shore of Great Diamond, ospreys often float and glide, sometimes diving into the deep waters below for fish. 

Make your way southwest, and you’ll see the big Peaks Island Casino building sitting at water’s edge. Built in 1930, it’s now the Peaks Island Sailing Club.

Going Ashore

Just beyond the Sailing Club, a long, inviting sand beach unravels all the way City Point. The boat ramp near City Point is an excellent place to stop if you would like to explore Peaks Island Town. Consider the tide when you pull your boat up on the beach.

If you walk up Centennial St. (the one leading up from the boat ramp) and then take your next right, you’ll follow Island Ave. right into the thick of town. Just past the bicycle rental place, there’s a little known but wonderful public restroom in the public library. A small grocery store sits across the street. Inside you’ll find a deli and sandwich makers. Beware the pickles they use on the sandwiches: they’re addictive. Continue farther down the road and you will discover ice cream.

City Point, with Little Diamond Island Casino overlapping Fort Gorges, and Portland in the background (Photo: Joe Guglielmetti)

Notice how a lot of the vehicles here are barely patched together with duct tape? That’s because there’s no motor vehicle inspection required on Peaks Island, so the rejects from the mainland have a colony here. You’ll also observe that some people simply use golf carts to get around!

 At City Point, you’ve circumnavigated! Congratulations. From here, you’re back bearing to Little Diamond, Fort Gorges, and East End Beach.

 A NOTE ABOUT SAFETY: Sea kayaking responsibly on Maine's coastal waters requires preparation, skills and knowledge. Casco Bay is a potentially dangerous environment due to its very cold waters, busy boat traffic and exposure to the conditions of the Atlantic Ocean (including sudden fog and strong winds). This is why we encourage people to take our lessons or join our guided trips before venturing out on their own. One fundamental skill that is essential for sea kayaking is the ability to rescue someone from a capsize. It can be extremely difficult to re-enter a kayak in cold and turbulent water. Anyone who paddles in the exposed waters of Casco Bay without this knowledge (or someone else who has that knowledge) is taking an extremely high risk.  Sign up for our "Rescue Clinic" to learn these rescue skills.


Local NOAA Chart (online viewing only):
Local marine forecast: