Early explorers of Casco Bay claimed it had 365 islands, leading to the colloquial name “The Calendar Islands.” While the actual number is only 136, each one has a personality of its own.
Thursday
Afternoon
The Casco Bay Lines terminal is buzzing with summer activity as locals and visitors shuffle onto the signature red, white, and yellow ferries. I’m Peaks Island bound, and it will be my home base for the next two days. I find a seat on the open-air upper deck, which offers unobstructed views of the bay and the Portland skyline as it shrinks behind me. To my left Fort Gorges sits proudly on Hog Island Ledge. This fort, which is covered in shrubs and trees, was built in the mid-1800s but never saw battle. To my right I can see a trio of lighthouses: Bug Light, Spring Point Ledge Light, and Portland Head Light. It’s a short 20 minutes before we are pulling into the Peaks Island terminal. Passengers spill out and go their various ways. Many take off on golf carts (the preferred method of transportation on Peaks). The beautiful Inn on Peaks Island is just up the hill from the terminal. I check in and take a moment to enjoy my room’s water-facing balcony.
The Fifth Maine Regiment Museum is having an art opening and I opt to head over on foot. I take a direct route through the island’s residential neighborhoods and admire the various cottages and homesteads. e bright buttery yellow museum sits just above the water on the southern coast of the island. It originally served as a headquarters for the fifth regiment Maine volunteer infantry and has since transitioned into a cultural center for the island and its residents. Inside beautiful stained-glass windows are adorned with the names of soldiers, and display cases contain Civil War-era relics. A vast veranda overlooks the bay. The opening exhibit, Off-Season: Island Photographs by Heather Wasklewicz, provides a look at a quieter side of Peaks during the less busy months when the summer crowds have disappeared.
Evening
For dinner I stop into the timeless Hannigan’s Island Market. Locals catch up with summer residents returning for the season, and the store clerks seem to be on a first-name basis with almost all of them. I order a simple meal consisting of an Italian sandwich and a bag of chips and enjoy it while the sun goes down on my hotel balcony. My last stop for the night is the American Legion. is classic, dimly lit haunt is a mainstay for locals and visitors. I order a beer at the bar and chat with some year-round residents before heading back to the Inn on Peaks.
Friday
Morning
Lisa’s Peaks Island Café is bursting with hungry breakfast seekers and the line is practically out the door. Inside, a long wrap- around counter serves as a centerpiece, behind which two employees are busy taking orders and frying eggs. A local from the legion hall tipped me off to the cinnamon buns, which look irresistible. I leave with a good-sized one and can’t resist adding a breakfast sandwich as well.
There isn’t a cloud in the sky and it’s a perfect opportunity to hike the entire island loop. The coast offers non-stop vistas of Casco Bay. The rocky shoreline is littered with small cairns, (piles of delicately balanced rocks) which seem to be an island tradition. Visitors cruise by in rented canoes and paddleboards. I stop into Take a Peak, a small shop with several cool island-themed gifts, as well as clothing and home decor. I also find the Gem Gallery, a fun spot featuring jewelry and artwork. Perhaps the most unusual stop is the world’s only Umbrella Cover Museum. This is exactly what it sounds like, a Guinness World Record setting collection of umbrella covers where Nancy, the owner, invites you to “come in and celebrate the mundane.”
Once I make it to the back side of the island I find myself at Battery Steele. is concrete behemoth was heavily armed and fortified in World War II to protect Portland Harbor. Now highly overgrown with vegetation and painted in graffiti it serves as a funky place to explore. Inside I walk through a long dark echoing hallway and poke into the various nooks and crannies. I finish my walk and find myself back at the ferry terminal. Before heading out for more island adventures I hit Down Front, where the team is working hard scooping ice cream into cups and cones for visitors. I get two scoops of Deer Tracks and hop aboard the noon ferry back to Portland.
Afternoon
It’s time to explore some of the other islands and sights in Casco Bay, so I’ve opted for the Casco Bay Lines Mail Boat Run. The mail boat goes out daily to Little Diamond, Great Diamond, Long, Cliff, and Chebeague Islands delivering freight to residents. The cruise is also carrying passengers and sightseers, and due to the large turnout, a Casco Bay Lines employee is narrating the trip over a loud speaker. The mail crew is hard at work bringing packages containing everything from food to furniture. I’m amazed as they lower down a couch from a crane on the top level. The views aboard the mail run are incredible and offer unique glimpses of some island wildlife. A pair of harbor seals seems to be following the ferry, and a bald eagle scans the water over the forested edge of Great Diamond Island. At one point the narrator points out what at first looks like a lawn ornament, but upon closer inspection is a tiny lighthouse. At six feet tall, Pocahontas Light is the smallest lighthouse registered with the U.S. Coastguard. After an actual “three-hour tour” we return to Portland and I hop back on the ferry to Peaks.
Evening
The outdoor dining patio at The Inn On Peaks Island looks too good to miss and I find a water-facing seat to relax in while the sun goes down. For dinner it’s fried calamari and fish tacos with Shipyard Export Ale. I need to head back to the mainland in the morning, but I make a final stop into the legion hall for a nightcap and some conversation. Thirty- six hours is certainly not enough time to explore all of the Calendar Islands, but I hope to be back soon to see more of what Casco Bay has to offer.
