Written by Joe Guglielmetti


TRIP LENGTH:  14 Miles
HIGHLIGHTS: Paddling beside the Diamond Island cliffs, crossing Hussey Sound, camping on big sandy beaches, building windbreaks to prevent sand from blowing into your cornmeal
DEPART FROM: East End Beach
WATCH OUT FOR: Vessel traffic, tidal currents, the disappearing sandbar to the north of Little Chebeague
RELATED TRIP DESCRIPTIONS: Fort Gorges, Cow Island, Long Island

Much of Casco Bay is protected by outer islands like Jewell and Cushing that block the brunt of the wind and swells coming off the open ocean. This inner part of the bay offers relatively calm waters where wildlife flourishes, lobster boats bustle, and paddling is available to all skill levels. An overnight trip to Little Chebeague allows you to island-hop through this more protected inner bay, while still passing by many of the bay's most interesting sites and leaving the possibility of detours to the outer islands. If you like camping on white, sandy beaches, you'll probably enjoy a night on Little Chebeague. 

The little island is the sandy satellite of Great Chebeague, which is the second largest island in Casco Bay. The two Chebeagues connect at low tide by sandbar, allowing you to walk between them. Unlike almost every other island in Maine, fine sand makes up nearly all of Little Chebeague’s shoreline, the exception being a spit of granite to the west.

Despite its small stature, the island is replete with trails and campsites, and it even contains an old fire training structure from the U.S. Navy. A full time caretaker lives on the island during the summer months, but it's otherwise uninhabited these days.



Little Chebeague has a lot to offer kayak campers, but it isn’t always as remote or peaceful as many other Maine islands. It’s adjacent to busy lobster fishing communities and the primary channel to the outer islands. It’s also a popular camping destination for boaters of all types and it can experience heavy use in the summer. But it sure is a fun and unique spot -- even when you have to share it with some other folks!

Getting There

Start the paddle to Little Chebeague by crossing from the East End Beach to Fort Gorges, and then on to Little Diamond Island. Be cautious during this crossing. Boat traffic often moves around either side of the fort, including large pleasure yachts and working vessels. The tide creates strong currents here as well, especially during its ebb.

During the summer, the prevailing winds are southwesterly. A flag flies on the north side of Fort Gorges, and is a good indicator of the wind. The flag fully extends at about ten knots. There's no public access to the beaches on Little Diamond, so best to stop at Fort Gorges if you need a break.

Fort Gorges is a former harbor defense battery completed in 1865. It is owned by the City of Portland and open to the public. If you visit, be careful of trip/fall hazards that abound. (Check out our Fort Gorges trip description for more info)

There’s a small sandy beach on the west edge of Little Diamond that you should navigate toward. Once here, paddle north along the east shore, passing the old brown casino building at the ferry pier, built in 1905.

Look at this scenery! This is Diamond Pass, one of my favorite places in the world! To your east is Peaks Island, the busiest island community in the bay, and a great example of Maine island life. Up above you, on Little Diamond, beautiful homes overlook the water, and an abnormal number of deciduous trees grow from island soil.

Little and Great Diamond Islands are all private land, and connect at low tide where Lamson Cove opens between them. There’s a cool old shipwreck here; you see the ribs rise above the water at mid to low tide. This wreck was an intentionally foundered wooden ship.

As you move north and follow the coast of Great Diamond, the cliffs grow, and eagles and osprey often soar above. The final, clustered community across the pass on Peaks Island’s north shore is the Evergreen Village. Just off of its coast is Pumpkin Knob, a small island that was once John Ford’s summer getaway.

Paddle across the opening to Hussey Sound toward West Point, the west corner of Long Island. This crossing exposes you to the open sea, and you most likely feel the rolling swell and a drop in air temperature. The water exceeds one hundred feet deep in the middle of the sound. You’re likely to see harbor seals swimming and fishing here, because the underwater currents upwell a lot of marine life.

Once you reach Long Island, follow its west coastline. Pass plenty of sandy beaches, all public and friendly for visitors. Long Island is its own town, established in 1994 after succession from Portland. The townsfolk are very proud of their independence. There’s a public portable toilet on the ferry pier, and a small store that sells a variety of food and beverages just up the road from the public dock. They have a freezer with all sorts of treats. I once ate a whole box of powdered donuts here. Paddling makes me hungry.

Long Island got its name for a reason, and as you paddle north, you understand why. Long Cove, usually filled with lobster boats, breaks the straight shoreline. To the west, distant, you see the mainland. Between here and there, the Navy maintained an anchorage for the Atlantic Fleet during the Second World War. Imagine dozens of destroyers and battleships sitting out there! They sailed in and out through Hussey Sound.

Little Chebeague sits to the north with its white sand shore easy to spot.

Many lobster fishermen and women live along this section of Long Island, and their boats bumble around the docks, and head to and from sea. There’s a lobster co-op dock here where the catch is kept alive under water.

It’s best to cross from Long Island to Little Chebeague at Cushing Point, because it makes the crossing as short as possible. Be cautious of the constant boat traffic here. Great Chebeague sits just north, with its tall sloping landscape, and sparse habitation.

On Little Chebeague

The campsites on the island line up along the east shore, just above the beach. These sites are easy to access and allow you to carry your boats right up to the action. But nothing is ever perfect in camping. Camping here, the big disadvantages are the overabundance of sand, and lack of tree line protection. These factors are an especially important consideration when it’s windy. If a stiff wind blows up the beach, you can construct your own windbreak with a tarp if needed, and that will protect your cooking and belongings from filling with sand.

Little Chebeague has fewer trees than other islands, and it may be difficult to find a lot of dead firewood. Although it’s tempting to build a fire on the beach, only do so if you can find driftwood and fallen branches. Don’t destroy the few trees that live on the island!

When camping on Little Chebeague, your closest emergency services are on Long Island, which is a quick crossing back to Cushing Point. Remember to factor this in to your evening. If someone should be injured or fall ill, you will have to be smart about the fastest way to help them. Plan ahead!

Now go explore the Island! Just remember that the sandbar disappears at high tide, and poison ivy abounds! And give the island caretaker her/his space!

Departing Little Chebeague

Because you’ve already seen Diamond Pass on your trip out, it’s always interesting to take the alternative route back to East End Beach. There’s a long crossing to Cow Island if you head southwest. You can connect the dots with red buoys. Other than exposure to wind and some boat traffic, this crossing is protected and straightforward. If you’d rather follow Long Island again, and cross to Cow from Ponce Ledge, that is also a straightforward route.

Paddle around the west shoreline of Cow Island. There’s a public area here complete with fancy latrine, well known as the best in the bay. Cow Island is sometimes busy with adolescents because it’s the home of Ripple Effect outdoor programs. You’ll see evidence of the military bunker that operated on Cow Island until the end of the Second World War.

The crossing between Cow and Great Diamond Island is short, but sometimes surprises a paddler with strong tidal currents, and sudden blasts of wind from the open ocean at Hussey Sound. Make an assessment of the conditions before crossing. Diamond Cove opens to the east, and is the old landing for the Navy at Fort McKinley, which operated in the early 1900’s.

Follow the west shore of Great Diamond Island. You can already see East End Beach quite distant, under the big ugly apartment buildings in Portland. Though it’s tempting to just begin paddling toward your destination, it usually makes more sense to paddle along the shores of Great and Little Diamond Islands, and then cross just west of Fort Gorges. This will keep you less exposed to wind and vessel traffic, and allow you to stop onshore if needed.

 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:

Leave no trace principles:

Little Chebeague Island Trails/Campsites:

Maine Island Trail Association: