Paddle Portland Harbor

A Guide to Paddling Portland Harbor 

The many wharves of Portland Harbor. Click on the map above to expand the image.

Portland’s historic Old Port

Portland’s historic Old Port is almost always packed with visitors strolling its cobbled streets and boats cruising in and out of its wharves. If you have the knowledge and experience to navigate the harbor in a kayak or SUP you can get a close-up view of the working waterfront and the many traces of the port’s long and fascinating history. Just keep in mind that this is a working waterfront; it’s important to stay out of the way of fishermen and others who are rely on the harbor for their livelihood.

For this trip, we’ll describe the highlights of a paddle that begins at the East End Beach and continues up the Fore River past the Old Port towards the Casco Bay Bridge. For the return trip we’ll describe a route that follows the South Portland shoreline to Bug Light, Spring Point Ledge Lighthouse, then back to East End Beach.

AN IMPORTANT NOTE ABOUT SAFETY: Paddling Portland Harbor is not for novices or anyone without significant experience navigating busy boat traffic. There are many potential hazards, and local knowledge is crucial. Novice paddlers are better off joining a guided tour. Click here to sign up for one.

Rounding Fish Point, Entering the Fore River 

We’ll start our paddle by following the shoreline of the East End Beach heading southeast until the sand turns into rock and the shoreline veers to the south. This spot is called Fish Point (it’s always been a terrific fishing spot), and it marks one side of the mouth of the Fore River. A short distance out from shore you’ll see a large green buoy marked with the number “1.” This buoy indicates where vessel traffic increases, whether you’re crossing toward South Portland, or towards Fort Gorges to the east. Today, we’re making a right turn before or at the buoy and heading up the Fore River.

At this point you’re paddling along the shoreline of the Eastern Promenade park, which was conceived in 1836 when Portland’s civic leaders began acquiring waterfront land to ensure that all residents would have access to public green space along the shoreline. After the turn of the century Mayor James Phinney Baxter hired the legendary Olmsted firm to develop an ambitious plan to make the Eastern Promenade a premier city park.

In the summer, there’s often a firm southwesterly wind moving along the lowland of South Portland, right through the Fore River, and it passes directly over Fort Gorges. It’s often difficult to appreciate this wind until you emerge from the protection of the Eastern Promenade. During the non-winter months, an American flag flies on the north side of Fort Gorges, 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).

Fort Allen Park & the USS Portland

Fort Allen Park is just uphill from rocky Fish Point

Fort Allen Park is just uphill from rocky Fish Point

As you round Fish Point you can look up the steep embankment on your right to view Fort Allen Park, where a fort once sat to defend the city from the British during the War of 1812. It’s the perfect spot for a fort: the cannons at the top of the hill could easily strike invading ships below, but it would be very difficult for cannons on the ships to fire back at such a steep angle.

You’ll also notice the mast the towering mast of the USS Portland, a WWII Navy cruiser that was one of the only warships to serve continually throughout the war and participate in almost all the major naval battles. She took damage several times, including from a torpedo during the Battle of Guadalcanal.

After you paddle further along the shoreline, through the mooring field and past the marina you’ll observe the small dock area used by Sail Maine and Ripple Effect -- two local organizations that help young people learn about the sea through sailing and kayaking. Be mindful that the intrepid young sailors in the small numbered sailboats may be learning, so give them space, especially when they’re engaged in a regatta.

The Portland Company & Narrow GAUge RR


Onshore you’ll see the brick facade of the Portland Company, which was established in 1846 to manufacture locomotives for the Atlantic & St. Lawrence Railroad. The company built 600 steam locomotives as well as 160 other marine and terrestrial vessels, including the engines of the civil war side-wheel gunboats Agawam and Pontoosuc. The Portland Company finally shut down in 1978. Today that entire area of the waterfront is on the verge of a massive redevelopment. Some of the historic structures will remain, but expect to soon see condominiums, lots new storefronts and a much bigger marina.  

If you look closely onshore you’ll see a statue of a man standing beside the marina. This is a statue of George Cleeves, the first European to establish a village in what is now Portland, and what was then called Casco. Of course, Abenaki people had been living in the area for long before Cleeves arrived in 1632. It wouldn’t take long for tensions between newcomers and the natives to erupt into all-out war. In 1676 the Abenaki completely destroyed the village Cleeves established and drove settlers from the region. This was the first of four times that Portland would be destroyed in its history.  


So far you’ve been paddling alongside the Narrow Gauge Railroad that since 1993 has offered passenger service along the 1.5-mile railroad tracks that extend from your current position to the now-defunct swinging bridge at the mouth of the Back Cove. You may see their historic steam and diesel locomotives packed with waving tourists.

From Burnt Pilings to the INner Harbor

Pilings portland harbor.jpg

Ahead you’ll see a forest of charred pilings sticking out of the water. It’s fun to paddle through a fairly narrow passageway to the right of these pilings, just beside the shoreline.

You'll paddle past the burnt pilings that once supported wharves servicing the Grand Trunk Railway and it's massive grain elevator. (Maine Memory Network)

You'll paddle past the burnt pilings that once supported wharves servicing the Grand Trunk Railway and it's massive grain elevator. (Maine Memory Network)

These burnt pilings once supported expansive wharves that serviced the Grand Trunk Railway, which ran from Portland to Montreal. After the railroad was built in the 1850s much of the grain and other commodities that were produced in the interior of Canada were transported on the railroad to Portland, where they would be loaded on ships to be distributed to global markets. During the second half of the 1800s Portland became a major commercial hub as it became increasingly connected to the rest of the world by steamship routes and railroads.

In 1974, long after the railroad’s demise, the towering grain elevators that were built to hold all that Canadian grain caught fire. The blaze spread to the wharves and demolished them for good.

The charred pilings of the wharves have remained since the fire, offering gulls and cormorants a place to perch and providing a home for a family of ospreys, which built a nest atop platform provided by the City of Portland. Make sure you spot the large osprey nest as you paddle through the pilings, but don’t get too close or you’ll agitate the ospreys.

Kayaking paddling past Ocean Gateway Terminal, with the Portland Observatory visible on the horizon

Kayaking paddling past Ocean Gateway Terminal, with the Portland Observatory visible on the horizon

A very long and narrow pier extends along the south side of the pilings from a complex known as Ocean Gateway Terminal that is the main entry point for large passenger ships docking in Portland. In the summer and fall months you’re likely to see an enormous cruise ship tied up to the dock. If one is present, you should stay clear -- especially when it’s underway. Always look to see if their dock lines are attached to the dock; that’s a good indicator of whether or not they’re in motion. Monitoring channels 16 and 13 on your VHF radio will also help you hear what marine traffic may be up to.

As you pass Ocean Gateway look back toward Munjoy Hill and check out the view of the 86-foot high Portland Observatory, built in 1807 by Captain Lemuel Moody. It might look like a lighthouse but it was designed to serve a very different purpose. This was a commercial venture designed to give a competitive edge to ship owners who paid Moody a subscription fee of $5.00 a year to alert them when their ships were arriving. During the 19th century there were naval observatories like this in many cities, but very few are still left standing.

Beyond the big glassed-in building at Ocean Gateway, the Cat, a ferry to Yarmouth, Nova Scotia, docks daily in summer. (Though the latest word is that it will not continue running in 2019). The ferry’s schedule has changed over the years, but currently the ferry comes in and out once during the early afternoon. Keep a watchful eye. If the ferry is out you can carefully paddle straight under the Ocean Gateway building. If the ferry is in you should only cross its bow when you are sure it’s not underway.

Cross from Ocean Gateway to the Maine State Pier, keeping watch for the tugboats that are stationed along the pier and that often maneuver in and out as the assist large ships.

To your right you’ll have a view up India Street and the oldest neighborhood in the city. English colonists resettled here and built Fort Loyal in 1678 after being driven out by the Abenaki two years earlier. It didn’t last long! An army of more than 400 allied French and Indian attacked the fort in 1690 and exiled the English for another ten years.

Portland wharves in 1890 (Maine Memory Network)

Portland wharves in 1890 (Maine Memory Network)

That French and Indian attack was the second time Portland faced destruction. The third case of widespread destruction occurred on the verge of the American Revolution when English naval Lieutenant Henry Mowatt bombarded the city for nine hours, leaving three quarters of the city in ashes. The attack was meant to punish residents for supporting the Boston Tea Party and other acts of Patriot resistance, but instead it solidified the local commitment to independence. The burning of Portland is one of the grievances against King George cited in the Declaration of Independence.

Paddling Past the Old Port 

As you pass the southern tip of the Maine State Pier you’re entering inner Portland Harbor, where there’s a lot more boat traffic. There’s also a no-wake zone here, which means that all boats must slow to headway speed only.

Fishermen often cast lines from the end of the pier, so give them space while passing. On the west side of the pier working fishing boats dock and depart all day long in the summer. This slipway is probably the busiest section of the harbor.  You can expect traffic from three schooner tour boats, the Casco Bay Lines ferries, the Portland Fire Department boats, and many pleasure boats.

The boat traffic combined with the long casts of the fishing lines at the end of the pier makes this a tricky area for a wayward kayaker to navigate. Look both ways, wait for traffic to clear and then move as quickly as possible across this brief section of water. If you need a target, head straight across toward the marina at Dimillo’s floating restaurant if it’s morning, or, if it’s afternoon, head for the big red letters that say “Lobsters” at the fish processing plant to the right. The difference in timing is because of lobster boat traffic, which wanes in the afternoons.

When the lobster boats are docked, the waterway between Portland Pier and Custom House Wharf is a neat place to check out. You can paddle all the way between them and find a nice calm stretch of water  to take a break and get a close-up look at the boats.

Up until the 1850s the waters of Casco Bay reached nearly to Fore Street, far beyond where Commercial Street and all the wharves now sit. The shoreline of the port was extended further and further over the decades in order to make room for railways and increasing commerce. During big storms the waters still rise high enough at high tide to flood many parts of Commercial Street. As sea levels rise in the coming decades we can expect flooding to become an increasingly significant problem.

Soon you’ll reach Dimillo’s Floating Restaurant, a former Staten Island Ferry that is permanently docked at the Long Wharf. The slipway between the Long Wharf and Chandler’s Wharf is probably the second busiest area of Portland Harbor, with several tour boats and many yachts moving in and out all day long in the summer.

Chandler’s Wharf stands out because it’s lined with condominiums. This development, completed in 1988, stirred lots of controversy. For decades locals, and especially fishermen, have been concerned that commercial development and tourism-focused businesses will eventually displace the working waterfront and the fishing industry. The city now has rules in place that limit non-marine related business uses on the wharves, but the fishing industry continues to face many headwinds. A coalition of fishermen are currently advocating for further restrictions on development to ensure that the working waterfront doesn’t disappear.

Chandler's Wharf to the Casco Bay Bridge

Beyond Chandler’s Wharf, the densest stretch of the working waterfront begins. From here to the Casco Bay Bridge you’ll see almost entirely commercial fishing traffic, boat yard, and fish processing. Though initially industrial in its aura, this section of waterfront is quite beautiful in its own right. As you paddle along this section, remember than few major coastal cities in the United States still have significant fishing oriented waterfronts.

It was in this part of the harbor that a group of boys playing with fireworks sparked a massive fire that burnt down much of the city. The Great Fire of 1866 occurred on July 4 and left more than 10,000 people homeless. This was the last time that the city faced widespread destruction.

You’ll see a massive crane rising up ahead just before the Casco Bay Bridge. This is the international container ship terminal operated by Eimskip, an Icelandic company. All the shipping containers stacked up along the shore will eventually be shipped to Europe. This relatively new connection to the world is part of the recent revival of Portland as a major American port.

The Eimskip shipping container terminal

The Eimskip shipping container terminal

There is only space for one container ship, so if it’s in make sure it isn’t moving before you venture past and under the bridge. Tankers carrying various petroleum products, and other cargo ships, often sail up through the drawbridge and into the upper Fore River.

Paddling under the Casco Bay Bridge is exciting. This is one of the tallest drawbridges in the United States, and it was opened to traffic in 1997. Just before construction of the bridge was finished the old bridge was struck by a Liberian oil tanker, the Julie N, leaking 179,000 gallons of oil into Casco Bay. Most of the toxins that entered the bay were recovered, but the cleanup cost $43 million.

The South Portland Waterfront 

Make your way to the South Portland side of the harbor. If you need to take a break and stretch, there’s a small beach on the South Portland side of the bridge, just east of the causeway. It’s not the most scenic beach, thanks to the electrical transformers nearby and the bridge traffic above, but it’s a good resting spot. You can also land alongside the public dock just under the bridge.

Paddle along the South Portland side of the Fore River heading northeast. This side of the river isn’t as busy as the Portland side, so you can relax a bit more. The Coast Guard station appears to the right, and beyond it a large marina with many docks and moorings.

After the marina, one of the Portland Pipeline oil docks extends into the harbor, and there’s usually a barge there, and sometimes a tanker. After rounding this dock, the smallest lighthouse in Maine appears on the shore to the right. Constructed in 1886, Portland Breakwater Lighthouse is known by locals as “Bug Light”. It once sat at the end of a half-mile long breakwater, but during the Second World War, the land that is now Bug Light Park was filled in to create a shipbuilding yard.

Up ahead you’ll see the Portland Pipeline, which carries oil all the way to Montreal. Do not pass under the large pipeline dock and be careful as you paddle around the outside; sometimes very large oil tankers from faraway lands dock here.

Beyond this dock you see Spring Point Ledge Lighthouse, built in 1859. For much of its life, this “spark plug” style lighthouse sat on the ledge with no breakwater connecting it to land. The breakwater came in 1955 to help protect the nearby marina from ocean swells.

From the lighthouse, proceed to the green buoy marked “5” off of Bug Light. This is a very good location to scan marine traffic prior to crossing the busiest corner in and out of the harbor. It's also a good idea to make a "securite" call on your VHF radio to notify boat traffic of your crossing. Once you're ready to cross you can very carefully paddle quickly and directly back towards the number 1 green buoy by Fish Point. You can also use the large, tan apartment building on the hill (the Portland House) as a landmark beside Fish Point to help you use a range as you cross. 

 ANOTHER 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:
Marine forecast for the Portland Harbor:
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