When it’s May and the weather forecast for your weekend is two days of sun with highs near 70, you don’t think twice — you load up the kayaks and drive to Maine!

Casco Bay stretches from Portland Head to Small Point, and includes many of the islands with year-round communities that remain in Maine. It’s a busy place, with big ships,  ferries, local fishermen, and lots of recreational boats. The best time to visit is during the off-season, when the campsites aren’t packed and the launch sites have parking. Therefore, fellow employee (and fiancee) Kristen and I decided to spend two days in Casco Bay!

Jewell Island offers a protected harbor lined by low cliffs. The campsites are located at the top of the cliff, and offer great views back toward the mainland. Here, Kristen watched the sunset.

We put in at Falmouth Foreside Town Landing and made the long crossing to Great Diamond Island. After following the cliffy southern shore of Great Diamond and Little Diamond, we landed at Fort Gorges, an 1865 granite fort built to protect Portland during the Civil War but never used. The fort is owned by the City of Portland and open to the public. We wandered through the officer’s quarters, explored the pitch-black powder magazines with our headlamps, and climbed to the top of the three-story structure for a great view of Portland and eastern Casco Bay. Most of the fort has decayed significantly, but in places you can still see ornate woodwork, fully intact wood floors, and a beautiful spiral staircase.

We hopped back in our boats and crossed the shipping channel to Spring Point Light, then paddled down the rocky South Portland shore to Portland Head Light. One of the best-known and most-photographed lighthouses in the world, Portland Head guards the western entrance to Portland Harbor. It’s a beautiful structure in a beautiful spot, and the tourists that flock there stare longingly at any kayakers who happen to paddle by. It’s also totally exposed, and the 3- to 5-foot rollers coming off the sea were lots of fun as we left Portland Head behind and headed back across the shipping channel to even-more-remote Ram Island Ledge Light off Cushing Island. Both the design and the loneliness are reminiscent of the Graves Light in outer Boston Harbor. With the rollers now giving us a boost from behind, we skirted White Head on Cushing Island, perhaps the most spectacular rock cliff in Casco Bay.

From there it was on to Jewell Island, our campsite for the night. Jewell is the largest island on the Maine Island Trail (MITA), with stunning rock cliffs, a protected cove ringed by campsites, and miles of hiking trails that explore beaches, swamps, and the remnants of military buildings from both World Wars. After 16 miles of paddling and a well-deserved dinner, we took a short hike and turned in to the sound of surf breaking on the far side of the island.

In the morning, we hiked across the island to the Punchbowl, a large tide pool ringed by a sand beach. Following the rugged rocky shore south from here, we climbed to an amazing vantage point high above the surf and shot this video.

After a delicious breakfast of eggs and sausage, we broke camp and started to make our way back to the put-in. Our first stop was Bangs Island, another MITA island open to visitors. On the south end, terns flew overhead and abruptly dove headfirst into the water, hoping to snatch unsuspecting fish with their bills. On the west side, we saw one Laughing Gull standing in the back of another while flapping his wings and squawking loudly, and had to look twice before we decided “oh my, yes, that is what’s going on.” We stopped on Bangs for a quick snack before continuing to Little Chebeague Island.

May 17-18, 2012. Kristen and I launched at Falmouth Foreside and camped on Jewell Island. Click the image for a large map with more placenames.

Little Chebeague is yet another MITA island, and one of the most interesting (there are 20 or so islands open to Maine Island Trail Association members in Casco Bay alone). Little Chebeague was a getaway for wealthy Portlanders and sported a hotel, bowling alley, golf course, farm, and numerous cottages at various times during the last 150 years. The Navy took over the island during World War II and used it as a recreation ground for thousands of sailors manning the Atlantic destroyer fleet. They also constructed a small metal building that was doused in gasoline and ignited to simulate fires on ships, and over 15,000 sailors took the firefighting course here in 1944 and 1945.

This firefighter training building, along with remnants of many cottages, are still visible on the island. MITA volunteers maintain trails throughout the island and have posted interpretive signs at many of the decrepit structures. It’s fascinating to see the old photos and pick out recognizable shapes still visible in the collapsed buildings.

By now the wind had picked up, and the remaining three miles to Falmouth were a fun, fast ride in some chop. Off Clapboard Island we saw a number of seals hauled out on a rock while a Bald Eagle perched on the peak. It was a fitting end to a perfect trip!

[Editor's Note -- If you paddle in Maine, a membership in the Maine Island Trail Association is a must. You'll gain access to almost 200 public and privately owned sites, plus an amazing guidebook to help you plan your travels. Visit mita.org to learn more!]