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Islands of Casco Bay

You can see them just off-shore from Portland, their lights twinkling off the water. They’re the Islands of Casco Bay, some with small towns and villages that have stood for generations. The Casco Bay Islands offer fun places for walks, bicycle rides, relaxed meals and a slowed-down pace far removed from that of mainland, urban New England.

To get to the islands, take the Casco Bay Lines ferries from Portland. Cruise to a single island or, for a sense of the Bay, take the Mailboat. Leaving several times a day, it visits five islands on a several-hours round trip. Feel like seafood? Ride the Lines’ Bailey Island Cruise, which sails to Bailey’s popular Cook’s Lobster & Ale House.

Things to Do on the Islands of Casco Bay

Casco Bay’s most populous island, Peaks Island, once boasted an amusement park, big hotels, spacious theaters and even active military installations. Those days are gone. Peaks is now a comfortable neighborhood of Portland (albeit an offshore one). But there are still plenty of things to do on Peaks Island. Leave your car on the mainland and see the island in other ways. Peaks Island Tours will show you the sights on foot or in stretched golf carts. Bikes are popular here; bring one on the ferry or rent locally at Brad’s Island Bike Rentals & Repairs (115 Island Ave., (207) 766-5631). History buffs should stop at the island’s Civil War memorial halls. Built in the 19th century by veterans as summer retreats, the Fifth Maine regiment hall is a museum. The Eighth Maine hall is a museum and lodge.

Maine Island Kayak Co. and Portland Paddle offers guided kayaking tours on the bay, including to hulking, granite Fort Gorges, which was built on rocky Hog Island beginning in 1858. You can paddle out and explore the massive and long-abandoned structure.

Chebeague Island is Casco Bay’s largest. It’s served by both Casco Bay Lines and Chebeague Transportation Company, whose ferries run from Yarmouth. Take a walk or enjoy some island golf at the 9-hole Great Chebeague Golf Club.

Great Diamond Island is home to many summer houses and a private residential community. Visit Diamond’s Edge Restaurant and the Inn at Diamond Cove, built on the site of the historic Fort McKinley.

Long Island is the year-round home to many fishing families. It’s also a great place for a hike or bike ride (bring one with you).

Cliff Island is the smallest island in the bay with a year-round community (about 60 folks) and is the last stop on the Casco Bay Lines’ run.

Restaurants on the Islands of Casco Bay

Good places to eat are scattered throughout the Islands of Casco Bay and include the Chebeague Island Inn; Diamond’s Edge Restaurant; Cliff Island Store & Café; and the Inn on Peaks Island. Scroll through our business listings below and check out these other locations for additional ideas.

Where to Stay on the Islands of Casco Bay

Casco Bay hotels include Chebeague Island Inn, the Inn at Diamond Cove on Great Diamond Island and Inn on Peaks Island. Check our business listings below for more suggestions.

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