Paddle to Whitehead Passage

Written by Joe Guglielmetti



TRIP LENGTH: 7 Nautical Miles
HIGHLIGHTS: Gazing up at the Cushing Island cliffs, reaching the open ocean, stopping on Peaks Island, watching guillemots land on water (it’s hilarious)
DEPART FROM: East End Beach
WATCH OUT FOR: Vessel traffic, venturi effect on winds and tide-current in Whitehead Passage, swell break on Trotts Rock, hazardously good pickles on the sandwiches on Peaks Island

Sometimes, you just want to island hop to the sea! Paddling from East End Beach to Whitehead Passage is the perfect progression from sheltered beginnings to an open-ocean-horizon. Along the way, you’ll move through some of Casco Bay’s layered history, observe wildlife and island life, and breathe the open-ocean air.

There are several routes you can navigate from East End Beach to Whitehead Passage, but here we’ll focus on the path that keeps you out of Portland’s primary shipping channel, and close to the interesting shorelines of the inner islands.


A regatta sails Whitehead Passage, photo: Joe Guglielmetti

A regatta sails Whitehead Passage, photo: Joe Guglielmetti

If you're starting from the East End Beach in Portland, the first crossing you’ll undertake is from East End Beach to Fort Gorges. A firm southwesterly wind commonly blows during summer, especially in the afternoon. You may not notice this wind until you emerge from Fish Point, but it will probably join you for the remainder of your voyage. During the non-winter months, an American flag flies on the north side of Fort Gorges, and it’s clearly visible from East End Beach. This flag is a solid indicator of the intensity and direction of the wind (the flag fully extends in a wind of 10 knots).

During ebb (outgoing) tide, Back Cove and the Presumpscot River empty between Fort Gorges and East End Beach at a steady pace. During flood (incoming) tide, there’s generally a slower but more “confused” current. It’s wonderful to time the tidal flow to assist your entire voyage, which works on this particular trip, because you can ride an ebb tide all the way out, and then pick up the flood tide for your return.

The federal government constructed Fort Gorges between 1857 and 1861 as part of the harbor defense system, which is now a layered museum of military structures from various wars throughout various islands and the mainland. Fort Gorges is now owned by the City of Portland. Yes, you can stop and visit and explore. Bring a flashlight, and watch your step.

Hey! You’re out on the water now! Feels great, doesn’t it? Portland is fading into a skyline behind you. Impressive, huh? That’s the largest city in all of Maine. And Portland’s harbor is the busiest harbor in New England (yes, even busier than Boston!). You’re now in a thoroughfare to inner Casco Bay, and there are many vessels passing through this space. Look out for yourself, always assume other vessels don’t see you, stay out of the way, make yourself seen and heard, and always wave at people, because that’s what you do when you’re in a boat (unlike in a vehicle, although I’m working on changing that).


The west wall of Fort Scammel photo: Joe Guglielmetti

The west wall of Fort Scammel photo: Joe Guglielmetti

There are a few options for the route beyond Fort Gorges, all equally fulfilling. You can head toward Little Diamond Island to the North, crossing over the old “escape channel” for the Navy during the Second World War. This was the channel through which destroyers and battleships would have sailed to sea had the anchorage in inner Casco Bay been attacked.

You can also head directly toward Peaks Island, which is a little more direct, but will require spending more time in the ferry routes. Otherwise, you can paddle over to House Island.

As with any crossing, your choice should partially depend on wind and boat traffic, and partially on what specifically you want to gander at. Remember, you’re coming back (hopefully), so you can choose a different route on the return trip to add some variety.

If you take the Little Diamond route, follow the southeast coast for a short distance, and then hop over to Peaks. Little Diamond does not have any public spaces. If you cross directly to Peaks, use the big yellow anchorage buoy as your bearing until you’re halfway across, and then navigate to the big green wharf.

If you cross to House Island, use the green navigational marker on the north shore to hold a bearing, and if you paddle to it, you will find an osprey nest inside. Try to stay distant enough to avoid scaring the ospreys. If you do scare them, note how they take their fear and aggression out on other birds instead of you, often dive-bombing nearby cormorants. House Island is a privately owned space. Jutting out from its west side, you can see Fort Scammel, a huge artillery bunker constructed during the tension leading to the war of 1812. Now cross from House Island to Peaks.

A seal hauled out on Hog Island Ledge, photo: Joe Guglielmetti

A seal hauled out on Hog Island Ledge, photo: Joe Guglielmetti

All three crossings involve ferry and tour boat routes, and plenty of lobster fishing groves, so pay attention to vessel traffic! Nowadays (unlike in the late nineties), paddlers and commercial vessel operators enjoy a pretty darned amicable relationship; so don’t ruin that of the rest of us!

Need a toilet already? No problem. Peaks Island provides a public restroom in the back corner of the parking lot just up from the ferry dock, which is the big green wharf that says “Peaks Island” in orange letters. Peaks has food and drink on Peaks as well. There's a small grocery store with a built-in sandwich shop, and their pickles might be the best you’ve ever tried. You can also visit Down Front Ice Cream if you’re warm, or just obsessed with ice cream like me! 


Whitehead Passage divides the west coast of Cushing Island from the east coast of Peaks Island. Both islands have sandy beaches along this stretch, but the majority of the coastline is rock. The north shore of Cushing Island climbs into sheer cliffs that overlook the open sea. Punctuating their stunning presence are concrete submarine towers from the Second World War, right atop the hill. Cushing Island is all private property, with the exception of Fort Levett, the World War II base. Unfortunately, you can’t reach Fort Levett without crossing private property, unless you fly or parachute in.

Watch out for Trotts Rock. Swell from the open ocean loves to break, sometimes violently, over this shallow granite stump. A skinny pole with a red triangle marks the rock.

Cushing Island Cliffs, photo: Joe Guglielmetti

Cushing Island Cliffs, photo: Joe Guglielmetti

Whitehead Passage is relatively deep, and the shores on either side are relatively high, so a venturi effect kicks up here both hydro dynamically and aerodynamically. If the wind and tide combine in a northeasterly direction, you can be jettisoned to sea with surprisingly rapid speed. If you find yourself overpowered by this force, navigate with it, and attempt to paddle north and then west to Peaks Island’s eastern shore. The venturi effect will lose its force once you are far enough to the north.

Also, swell height at the mouth of Whitehead Passage is often significantly higher than the average on an ebb tide.

Look out for guillemots! They like to spend time in Whitehead Passage, and they’re a lot of fun to watch, especially as they land, totally ungracefully on their fat little tummies.

Like to surf your kayak? Whitehead Passage is great for that. When swell moves in from the northeast, really good surfing waves develop between Trotts Rock and Torrington Point, and wrap into the cove on the west side of the point. When swell moves in from the east, surfing waves develop just offshore from the 5th Regiment Museum (the yellow building with a tower).

On your return voyage, if you’re interested in getting really close to Fort Scammel, paddle west along the coastline of Cushing Island, and then cross to the fort, and pass alongside the western wall. Looking west you’ll see Fort Preble to the left of Spring Point Breakwater. Forts Scammel and Preble were constructed simultaneously, and intended to crisscross cannon fire over the harbor entrance, and scissor the wooden ships of the day apart! Moving on, you’ll then see Fort Gorges to the northwest and can navigate straight toward it. If you take this route, you’ll skirt up against the major shipping channel, so pay attention to the large red buoys and stay northeast (right) of them. 

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:

Fort Gorges:

Fort Scammel:

Fort Levett: