Imagine a place where the salty sea air mingles with the scent of pine trees, where the horizon is dotted with lighthouses and fishing boats, and where the pace of life slows down to match the gentle rhythm of the waves. This is the charm of Maine’s Casco Bay Islands, a coastal paradise that offers a unique blend of natural beauty, rich history, and vibrant local culture. Whether you’re a nature lover, a history buff, or a foodie, the Casco Bay Islands have something to offer you. Let’s embark on a journey to explore these enchanting islands and discover what makes them a must-visit destination.

Getting to Know the Casco Bay Islands

The Casco Bay Islands, also known as the Calendar Islands, are a group of islands located in the Gulf of Maine, off the coast of Portland. There are about 136 islands in total, ranging from small, uninhabited islets to larger islands with year-round communities. The most popular islands to visit are Peaks Island, Great Diamond Island, Little Diamond Island, Long Island, Chebeague Island, and Bailey Island.

Exploring the Natural Beauty

Maine’s Casco Bay Islands are a haven for nature lovers. Each island boasts its own unique landscape, from the rocky shores and wooded trails of Peaks Island to the sandy beaches and marshlands of Long Island.

  • Peaks Island: Known as the “Coney Island of Maine,” Peaks Island offers a variety of outdoor activities. You can hike the Island Loop Trail, explore the tide pools, or rent a kayak and paddle around the island.
  • Great Diamond Island: This island is home to Diamond Cove, a private community built on the site of a former military base. The island’s natural beauty is complemented by its historic charm.
  • Little Diamond Island: A peaceful retreat, Little Diamond Island is perfect for a quiet picnic or a leisurely walk along the shore.
  • Long Island: With its beautiful beaches and marshlands, Long Island is a great place for bird watching and beachcombing.
  • Chebeague Island: The largest island in Casco Bay, Chebeague Island offers miles of hiking trails and stunning views of the surrounding islands.
  • Bailey Island: Known for its unique “cribstone” bridge, Bailey Island is a picturesque fishing community with a rich maritime history.

Diving into History and Culture

The Casco Bay Islands are steeped in history, from their early days as fishing and farming communities to their role in World War II. Each island has its own unique story to tell, and there are many ways to delve into their past.

  • Peaks Island: Visit the Fifth Maine Regiment Museum to learn about the island’s military history, or explore the Umbrella Cover Museum for a quirky cultural experience.
  • Great Diamond Island: Take a tour of Fort McKinley, a former military base that’s now a National Historic Landmark.
  • Chebeague Island: Stop by the Chebeague Island Historical Society to learn about the island’s past, or visit the Stone Wharf, a historic site that’s still in use today.
  • Bailey Island: Explore the Land’s End Gift Shop, a local landmark that’s been serving visitors since 1959.

Savoring the Local Cuisine

Maine is famous for its seafood, and the Casco Bay Islands are no exception. From casual lobster shacks to upscale waterfront restaurants, there are plenty of places to savor the fresh, local flavors.

  • Peaks Island: Enjoy a lobster roll at the Peaks Island House, or grab a slice of pizza at the Down Front.
  • Great Diamond Island: Dine at the Diamond’s Edge Restaurant, known for its stunning views and delicious seafood dishes.
  • Chebeague Island: Visit the Chebeague Island Inn for a gourmet meal, or stop by the Slow Bell Cafe for some comfort food.
  • Bailey Island: Try the famous lobster stew at Cook’s Lobster & Ale House, or enjoy a meal with a view at the Giant’s Stairs Seafood Grille.


From their breathtaking natural beauty to their rich history and culture, Maine’s Casco Bay Islands offer a coastal paradise that’s just waiting to be explored. Whether you’re looking for adventure, relaxation, or a taste of the local cuisine, you’re sure to find it here. So why wait? Start planning your journey to the Casco Bay Islands today!

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