Kayaking Maine’s Orr’s and Bailey Islands

For thousands of years, humans have gone out on the sea alone in a kayak and experienced what might be the ultimate soul journey on the water. The Orr’s and Bailey Islands are part of the Harpswell Island chain located off the central coast of Maine.

Although they are but two of many islands in the area featuring a myriad of bays, coves, and wildlife that can be explored by kayak, Orr’s and Bailey stand out as some of the most magical spots to experience the joys of paddling.

cove at Orr's and Bailey Islands in Central Maine

Orr’s and Bailey Islands in Central Maine. Photo: Sherry Hanson

The Paddling Season

Kayaking season at Orr’s and Bailey Islands runs roughly from late May through September. Though, some enthusiasts extend their time on the water even later in the season.

Air temperatures in late May are between 43 and 65 degrees F (6 to 18 C). In October, the range is 37 to 59 degrees (3 to 15 C), while summer temperatures vary from 52 to 79 degrees (11 to 26 C). However, these are just averages, as plenty of days in July and August can sizzle in the 90s (30s C).

Outside of temperature, there are many places to put in on these islands, from quiet bays and coves to open ocean. Coves offer protected waters, while the larger bays will get choppy quickly if there’s even a slight breeze. For open-ocean outings, it’s essential to stay updated on weather and tide changes, especially in early spring or late fall.

Route 24 on Bailey Island with view of the water and fishing boats

Route 24 on Bailey Island. Photo: Sherry Hanson

Where to Go Paddling On Orr’s & Bailey Island

There are a few paddling routes available in this beautiful area. Here are a few to get you started.

Mackerel Cove to Merriconeag Sound

One of my favorite routes begins by launching from the small sandy beach area at Mackerel Cove on Bailey Island. Then, head south among the lobster boats and pleasure craft out around the end of the peninsula. Finish by paddling north to Merriconeag Sound.

There will be swells during the transition out of the cove to head into the Sound. But otherwise, this route is pretty smooth. You’ll cruise among brightly painted buoys that mark where the lobster traps lie.

Plus, if you plan accordingly, you can pull in at a variety of places for a taste of the day’s fresh catch, or try a local brew. Cook’s Lobster or the Salt Cod Café, located adjacent to H2 Kayaking Outfitters, offers excellent options. You could also paddle through the Bailey Island Bridge–a unique, crib-stone bridge that connects Orr’s and Bailey Islands–and tie up at the float behind Morse’s Cribstone Grill, which puts you back on Bailey Island.

Read More: Maine Lobster House Run By Kayak

Morse's Cribstone Grill in Orr's and Baileys Island, Maine

Yum! Morse’s Cribstone Grill. Photo: Sherry Hanson

Land’s End To Merriconeag Sound 

For a longer route to the Sound, you can launch your kayak from Bailey Island Beach at the tip of Bailey Island, below the end of route 24. Then, paddle south and around to the west side of the island. Finally, head north to go over into Merriconeag Sound.

If you put in here, make sure to visit the lobstermen’s statue on the ocean side of Land’s End Gift Shop. The figure is a bigger-than-life tribute to many folks in this region who make a living on the water.

On a good day with calm seas, you might choose to take a picnic lunch and paddle out to Eagle Island, home of the late Arctic explorer Admiral Robert E. Peary, instead of paddling into the Sound. On Eagle Island, there is a boat landing, and, in season, you can tour the explorer’s historic residence. This route is open water kayaking all the way.

Bailey Island Bridge To Mackerel Cove Or Land’s End

To change it up, you can also put in beside the Bailey Island Bridge adjacent to H2 Outfitters. From here, you can head south down Merriconeag Sound, past Graveyard, and Pott’s Points. Continue south to the entrance to Mackerel Cove or Land’s End.

H2 Kayaking Outfitters

H2 Kayaking Outfitters, which provides kayak rental, courses, and tours. Photo: Sherry Hanson

Bailey Island Bridge To Reed Cove

Paddlers putting in beside the Bailey Island Bridge on Orr’s Island can choose to turn north and head up the Sound, instead of going south on the open water route. The Sound is a great place to enjoy the scenery, take some photos and enjoy a relaxing float in the coves.

Bailey Island Bridge To Casco Bay

Another option when putting in at the crib-stone bridge is to go under the bridge towards the east side of the islands and head south for the open waters of Casco Bay. While paddling on the east side of Bailey and Orr’s Islands, the water is rougher, and paddlers need to pay close attention to the weather and tide information before heading out.

On the east side of the islands, though, views along the rocky coast are unforgettable. You can paddle towards Land’s End on your way to Casco Bay. Or head north to Lowell Cove on the south side of Orr’s Island after passing beneath the Bailey Island Bridge. Even if you stay within sight of the coast, it’s still all open water paddling.

Bailey Island crib-stone bridge

Bailey Island crib-stone bridge, an excellent point to start your kayaking adventure. Photo: Sherry Hanson

Enjoy Paddling On Maine’s Orr’s & Bailey Island

When I am out here in open seas in summer, my spray skirt is running with water, and I am often sweating under my PFD. But, the pure athleticism of paddling combined with the screams of gulls and the rocking of fishing boats at their moorings brings incredible satisfaction and peace.

As I watch the rocks along the coast, the occasional seal will pop up to look at me, and the sleek, dark cormorants often perch on ledges to dry their wings. When a fish jumps or seal surfaces, I know I am sharing a special moment with these water creatures that have come to meet me.

What is your favorite spot to kayak near Orr’s and Bailey Island? Have you tried any of the outings mentioned here? Let us know in the comments below.

Read Next:
Richard Carney: Maine’s Treasure Diver
Doing The Dog Paddle: Tips For Canoeing & Kayaking With Dogs
The First-Timer’s Guide To Kayaking
Paddlers, It’s Time To Stretch

Article first published on Sept 14, 2015, and updated with formatting changes and additional links on May 1, 2020

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