The Calendar Islands: A Newcomer's Guide to Casco Bay
Casco Bay's islands are one of Portland's best kept secrets. Right there in plain sight, just a short boat ride away, and genuinely unlike anywhere else in New England.
Casco Bay stretches roughly 200 square miles between Cape Elizabeth and Cape Small, and within it sit hundreds of islands. Some uninhabited granite outcroppings, others home to tight knit communities that have been here for generations. A handful are easily accessible by ferry. Each one has its own rhythm, its own character, and its own pull.
Here's a look at the islands you should know.
Peaks Island. The neighborhood just offshore
If you only make it to one island, make it Peaks. Just a 15 minute ferry ride from Portland's Old Port, it's the most accessible and most populated of the bunch. There are around 3,000 residents in summer and a quieter year round community the rest of the year. Peaks feels less like a tourist destination and more like a genuine neighborhood that happens to be surrounded by water.
Rent a bike, follow the 3.7-mile loop road, and you'll pass rocky Cairn Beach, sweeping ocean views, and a mix of weathered cottages and newer homes. Wind your way back toward the ferry dock and dine at the Cockeyed Gull for shrimp tacos or grab a seat on the deck at the Island Lobster Company for “trap-to-table seafood” for a fresh Maine lobster. Both are just a short walk from the ferry dock and have an amazing view of Portland's skyline across the water. It doesn't get much better than that.
Peaks Island overlooking Portland’s skyline.
Long Island. Unhurried, unplugged
Long Island has long been home to fishing families, and that heritage still shows. It's quieter than Peaks, more rugged around the edges, and genuinely off the beaten path. Bring your own bike and plan to spend a slow afternoon at South Beach before picking up cinnamon sugar doughnuts from the Byers and Sons bakehouse. This is the kind of island that reminds you what "slowing down" actually feels like.
Chebeague Island. The big one
Chebeague is the largest island in Casco Bay, and it carries that distinction with ease. It has a laid back, community driven feel. Play golf at the 9-hole Great Chebeague Golf Club, explore miles of walking paths, and a genuine sense of island life. Ferries run from both Portland and Yarmouth, making it one of the more convenient islands to reach. If you're thinking about island life as more than a day trip, Chebeague is worth a long look.
Great Diamond Island. History and quiet elegance
Great Diamond is a bit of a hidden gem. It's home to a private residential community and the Inn at Diamond Cove, built on the grounds of historic Fort McKinley, a former military installation with a fascinating past. The islands of Casco Bay have a long military history, used as outposts from the War of 1812 through World War II, and Great Diamond wears that history more visibly than most. It's a beautiful, unusual place.
Cliff Island. The end of the line
Cliff is the last stop on the Casco Bay Lines run, the farthest from the mainland, and the most special. It's the smallest island in the bay, spanning just under one square mile, with no paved roads, home to roughly 60 year round residents, and the kind of place where the word "community" means something real. There's a small store and cafe where you can pick up a lobster roll and catch up on local news, then carry it over to Stone Beach (aka “Rocky Beach”) for a picnic with views stretching out to the open Atlantic.
Cliff Island isn't for everyone. But for the right person, it's a perfect place to truly get away from it all.
Getting out there
All of the main islands are served by Casco Bay Lines, which runs year round ferries from the terminal on Commercial Street in Portland's Old Port. If you want to get a feel for the whole bay at once, take the famous Mailboat run and visit five islands over a few hours. This gives you a wonderful sense of the scale and variety of what's out there. For something more adventurous, Maine Island Kayak Co. and Portland Paddle both offer guided kayaking tours on the bay.
Whether you're new to Portland or just new to looking out at that skyline and wondering what's out there, go find out. The ferry's waiting.
Erin Haber is an Associate Broker and Owner at Town & Shore Real Estate, specializing in Greater Portland and Southern Maine's coastal communities. A Cape Elizabeth native licensed since 2001, she helps buyers, sellers, and relocation clients navigate one of New England's most sought after markets.
