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21 BEST Things to Do on the Casco Bay Islands in Maine

Maine is full of charming, beautiful cities and towns, and that includes those located on its many islands. In particular, the Casco Bay Islands offer wonderful opportunities to enjoy indoor and outdoor activities that you can’t experience just anywhere.

These islands off Portland Maine are known for their amazing ocean views, thriving marine life, and the fishing and lobstering industry. Whether you’re looking for hiking, relaxation, a beach trip, restaurants or somewhere to disconnect, there’s an island in Casco Bay that is just waiting for you to explore it.

Casco Bay Lines
Casco Bay Lines | photo via thmcjr

About the Casco Bay Islands

Casco Bay in Maine is located between Cape Elizabeth and Cape Small, and it includes about 200 square miles of land and water.

The Casco Bay Islands include hundreds of islands — some small and uninhabited while others are larger with established communities, each of which has its own charm and vibe. The most popular to visit are Bailey, Chebeague, Cliff, Great Diamond, Little Diamond, Long, and Peaks.

Getting to the Islands

Most of the islands can only be accessed via boat. Most tourists and residents utilize Casco Bay Lines vessels departing from Portland Maine. Bailey Island, however, is accessible via the Cribstone Bridge, so visitors do not need to take a ferry to get there.

Casco Bay Islands
Casco Bay Islands | photo via sailingcita

History of Casco Bay Islands

The Casco Bay Islands were named the “Calendar Islands” by Colonel Wolfgang William Romer in the 1700s. He gave the islands this title because he saw as many islands as there are days in the year (or on the calendar).

The islands have a rich military history because they were utilized from the War of 1812 up through World War II as military outposts and batteries. Remnants of military structures have remained on the islands and some have been repurposed into preserves, museums, and parks.

Throughout this history, Casco Bay has been active in the fishing and lobstering industry. Fishermen from Portland have been fishing in the bay and around the islands for hundreds of years.

Peaks Island-Casco Bay
Peaks Island | photo via mainechoseme

Outdoor Things to Do on the Casco Bay Islands

There are plenty of outdoor activities on the Casco Bay Islands whether you’re looking for something family-friendly, adventurous, or relaxing.

Explore one of the many beaches along the coast, get out on the water for a guided tour, or delve into the military history of the islands. Check out these outdoor options on your next visit to the islands.

Maine Island Kayak Co.

There’s no better way to explore the Casco Bay Islands than by sea. Check out Maine Island Kayak Co. for a sea kayaking adventure that’s sure to be unforgettable. The company offers small group kayaking tours for all kayaking abilities.

Tour guides will familiarize you with the basics before setting off on the tour. The tour includes popular local sites, history, and stops along the way.

You will get to see not only the sites but, if you’re lucky, also seals, bald eagles, and other ocean life. Tours go past or stop at various islands, so you’ll get to see each one up close.

Battery Steele-Portland
Battery Steele | photo via morgan_forrest

Battery Steele

Battery Steele on Peaks Island is an eerie tunnel walk and a neat place to explore. The structure was originally a World War II fortification that was used as an observation spot and gun battery. It was listed on the National Register of Historical Places in 2005.

Over the years, the structure has been graffitied, and many have come to enjoy the artwork that’s been spray painted on the walls. There’s so much to see and areas can be dimly lit, so be sure to bring a light source, like a flashlight or headlamp, if you would like to go into the structure.

The ground could get wet, so bring boots and a camera to take some pictures along the walk.

Great Chebeague Golf Club-Chebeague Island
Great Chebeague Golf Club | photo via theturnpiketour

Peaks Island Golf Carts

A great way to explore Peaks Island is via a golf cart. You’re sure to see many locals and tourists cruising around in them when the weather is nice.

The golf carts fit four passengers and can be rented by those who are 21 years old or older. Once you have a golf cart, you can easily access local sites, trails, shops, and restaurants.

Great Chebeague Golf Club

Looking for a challenging golf course during your visit to Chebeauge Island? Book a tee time at the Great Chebeague Golf Club. This golf course is known for its challenging seventh hole, a 110-yard par 3 hole. Golfers have to take a shot from Stone Wharf over Casco Bay to the green.

The course is known for being challenging for those with a low handicap, but don’t let that deter you from giving this course a try when you’re visiting the island. Also, the golf club hosts events throughout the open season — golf tournaments, Independence Day picnics, and socials.

The clubhouse was originally a farmhouse that was built over 200 years ago. It has earned a spot on the National Register of Historic Places.

Umbrella Cover Museum-Peaks Island
Umbrella Cover Museum | photo via littlebluebrary

Indoor Things to Do on the Casco Bay Islands

When you need to take a break from all of the outdoor excitement that the Casco Bay Islands have to offer, try one of these indoor activities. From unique museums to military history museums and art galleries, there are several indoor activities to keep everyone busy.

Umbrella Cover Museum

The Umbrella Cover Museum on Peaks Island is a unique museum experience that you won’t find anywhere else. The museum’s mission is to celebrate the “mundane in everyday life,” showcasing those little fabric sleeves that umbrellas come in.

The museum has umbrella covers from over 70 countries. What started as a personal collection has become a quirky and fun landmark for tourists to visit, take pictures, and learn about umbrella covers. The museum is open seasonally from Memorial Day weekend to Labor Day weekend.

Fifth Maine Regiment History Museum

Located on Peaks Island, the Fifth Maine Regiment Museum is a must-see for anyone looking to learn more about Peaks Island and military history. The collection of the museum focuses on Peaks Island’s origins, the Fifth Maine Regiment, World War II, and local artifacts.

The Fifth Maine Regiment was a volunteer Maine Civil War regiment from 1861-1864. The veterans of this regiment opened the museum at its meeting place to commemorate the regiment’s involvement in the Civil War. The collection has grown to include local Peaks Island history throughout the years.

The museum is family-friendly and run by a wonderful group of volunteers who are happy to share stories and history with visitors and answer any questions.

8th Maine Oceanfront Lodge & Museum

The 8th Maine Oceanfront Lodge & Museum is another great place on Peaks Island to learn about American Civil War history involving a Maine regiment. The museum has a collection of Civil War memorabilia, Civil War displays, documents, and the history of the members of the 8th Regiment.

On-site, the grounds are gorgeous and have a view of the shoreline for visitors to enjoy. The museum is no-frills but very informational. History buffs will love learning about the regiment, while children will enjoy the outdoor ambiance.

Cliff Island-Casco Bay
Cliff Island | photo via emilygrams_

Chebeague Island Historical Society

The Chebeague Island Historical Society is not just for history lovers but has something for everyone in the family. The historical society runs a small museum that features Chebeague Island artifacts and town history.

It holds community events — history lectures, temporary exhibits, archaeological dig finds, and suppers. It’s not only a museum and historical society but also a community gem open to all.

Richard Boyd Art Gallery

The Casco Bay Islands have several small art galleries to visit. Check out the Richard Boyd Art Gallery on Peaks Island for an enlightening art experience. The Richard Boyd Art Gallery features paintings, bronze sculptures, and clay works with a connection to Maine.

There’s always something new to discover at the art gallery because the exhibits change monthly. From landscapes and still life to contemporary abstracts and photographs, the diversity of the art in this small gallery is impressive.

Fort McKinley Museum

The Fort McKinley Museum at Diamond Cove on Great Diamond Island is another great museum for history buffs and curious minds alike. Fort McKinley is a former U.S. Army defense fort. The museum is small but well-run with tour guides regaling visitors with stories of the fort’s past.

The museum has a nice collection of shell casings, maps, photographs, and military memorabilia. If you find yourself in Diamond Cove, it’s worth a visit.

Crown Jewel-Great Diamond Island
Crown Jewel | photo via mainelylost

Popular Restaurants on the Casco Bay Islands

You don’t have to rush back to the city of Portland Maine for a delicious and affordable meal. The Casco Bay Islands have many options whether you’re looking for a casual dining experience or something a bit more upscale.

TIP: Some restaurants are open seasonally, so check the hours prior to visiting these great restaurants.

The Cockeyed Gull Restaurant

The Cockeyed Gull Restaurant on Peaks Island is a wonderful, family-friendly restaurant featuring seafood and meat entrees.

The menu has an array of food options — from appetizers of soups and salads to fancy entrees like salmon, New York strip steak, and fried haddock, as well as pub favorites like cheeseburgers and sandwiches.

Make sure to leave room for dessert because locals rave about the layered carrot cake. And, take your camera to capture the spectacular bay views.

Crown Jewel

The Crown Jewel on Great Diamond Island offers a menu that you’d expect to see at a fancy city restaurant. The appetizer menu has delicious options — oysters Rockefeller, lobster arancini, and snap peas.

For entrees, try the seared scallops, crispy pork belly, shrimp ceviche, or butter-poached lobster. The children’s menu has three options — a burger, hot dog, or popcorn chicken.

A full bar menu with signature cocktails, like the Crown Jewel Punch, is available. There’s a small dessert menu featuring shaved ice, chocolate mousse, and ice cream sandwiches for those looking for a sweet treat at the end of a meal.

Diamond’s Edge Restaurant-Portland
Diamond’s Edge Restaurant | photo via date.night.great.night

Diamond’s Edge Restaurant

Diamond’s Edge Restaurant is located on Great Diamond Island. It has amazing views of the cove and offers lunch and dinner with a full bar. The menu can change annually but typically features staples — New England clam chowder and crinkle-cut truffle fries for appetizers.

Fresh, Maine-caught seafood — a Maine lobster roll, Maine lobster and crab ravioli, grilled swordfish, and cedar-planked salmon — round out the entrees. Top the night off with a berry cobbler or classic creme brulee, and you’re sure to leave satisfied.

For those in a hurry, there’s also the Diamond’s Edge Market on-site, which offers grab-and-go meals, alcohol, salads, and sandwiches. The market is the perfect place to stop to grab picnic essentials.

Jones Landing Restaurant & Bar

Looking for somewhere that serves breakfast, lunch, and dinner? Check out Jones Landing Restaurant & Bar on Peaks Island. Open seasonally, it is located on the water, offering amazing sea views and friendly service.

The daytime menu features breakfast options like spiced apple French toast, Benedicts, and a classic egg and bacon plate. Morning cocktails are offered, including mimosas and bloody Marys. For lunch, try the chowder or buffalo wings and then a lobster roll, Jones burger, Reuben, or smoked salmon toast.

Dinner features a bar menu of popular appetizers like French fries or onion rings and buffalo wings. Sandwiches — such as grilled cheese and fish — and entrees — like lemon ricotta Alfredo and broiled citrus aioli fish.

Milly’s Skillet Food Truck-Portland
Milly’s Skillet Food Truck | photo via kels_eatz

Milly’s Skillet Food Truck

Located at Jones Landing on Peaks Island, Milly’s Skillet Food Truck has delicious options available to go. Patrons are welcome to get their food and eat on the Jones Landing waterfront deck.

The food truck has lobster rolls, fried fish sandwiches, burgers, gourmet tacos, and sides — like clam cakes, onion rings, and truffle fries. The food truck operates seasonally.

Il Leone

Another Peaks Island gem is Il Leone, an outdoor wood-fired Neopolitan pizzeria. This food truck operates from May to October. Even though there’s no restaurant to sit at, customers can enjoy their meal at one of the many picnic tables or take it to go. The picnic tables are well-shaded for hot summer days.

Most of the produce used to make the pizzas is organic — from the garlic to the heirloom cherry tomatoes. The pizzeria has unique flavors too — like the Aragosta, which is wood-fired Maine lobster with lemon, basil, garlic, and chili flakes on top of a pizza pie.

If you’re not in the mood for pizza, the food truck also has a few salads and gelato.

The Driftwood Inn-Bailey Island
The Driftwood Inn | photo via ramsayhillary

Hotels on the Casco Bay Islands

The Casco Bay Islands have several relaxing and clean accommodations for solo travelers, couples, and families. Instead of traveling back and forth on the ferry, book a night or several at one of these charming inns.

The Driftwood Inn

The Driftwood Inn, located on Bailey Island, is a wonderful lodging option with both rooms and cabins. The inn has a saltwater pool for kids to cool off, waterside porches for relaxation, and, of course, amazing views of Casco Bay.

Rooms are spread across three buildings — the Driftwood building, the Surfside Building, and the Pleasant Place building. Each building has its own charm and offers twin, double, queen, and king beds. Most of the buildings have shared bathrooms.

The cabins are quaint and accommodate two or three people, depending on which one you choose.

Chebeague Island Inn

If you’re looking for scenic bay views, Chebeague Island Inn has you covered. Featuring a huge wraparound porch located on a hill, the views can’t be beaten.

While relaxing and enjoying the beauty around you, you can order a drink that will be delivered to you on the porch. This family-friendly inn has yard games — like cornhole and croquet — and a nightly bonfire at the fire pit to keep everyone entertained.

There are seven room types to choose from. All of the rooms include free Wi-Fi and clean furnishings, linens, and custom Maine artwork. You won’t find air conditioning, TVs, elevators, or phones here because the goal of the inn is to disconnect from the craziness of everyday life and enjoy island life.

There is a restaurant located on-site, offering breakfast, lunch, dinner, dessert, and Sunday brunch.

8th Maine Oceanfront Lodge & Museum

The 8th Maine Oceanfront Lodge & Museum on Peaks Island is ideal for budget-conscious travelers. This no-frills lodge has one, two, and three-bed rooms that are clean and comfortable.

Each guest is assigned a table and a refrigerator when they arrive. You are encouraged to share a meal with each other throughout the stay. Coffee and tea are free of charge, and many guests even bring their favorite coffees and teas to share with others.

On-site activities include puzzles, ping pong, free Wi-Fi, tide pool exploration, and enjoying the friendly atmosphere. Plus, the lodge is a gathering place where guests can learn about the Civil War and the 8th Regiment at the small museum that’s on-site.

Chebeague Island Inn
Chebeague Island Inn | photo via loretta_alkalay

Log Cabin – An Island Inn

If you’re visiting Bailey Island, consider staying at the Log Cabin island inn. This small, family-owned inn is the perfect place to rest between outdoor excursions in Casco Bay. Beautiful views and a quiet atmosphere provide the ideal place to relax and unwind.

Each room has a Maine theme, such as York, Westview, Casco Bay, and Bluefin. Some rooms have chairs, a deck, or a small kitchen area. There is a small restaurant located on-site for breakfast, lunch, and dinner.

Peaks Island-Casco Bay
Peaks Island | photo via loriasimpson

The Inn on Peaks Island

The Inn on Peaks Island has seven Maine cottage luxury rooms featuring Jacuzzi tubs, views of Portland, and private decks. This inn is great for large groups because it has a top-floor suite that can accommodate up to 11 guests.

Every room is bright and spacious and has luxury linens. Some rooms have fireplaces and balconies, but all rooms have free Wi-Fi and parking. There is a restaurant located on-site, but it is only open during peak season — spring through summer.

FAQs About the Casco Bay Islands

Are there beaches on the Casco Bay Islands?

Yes! The Casco Bay Islands have numerous beaches. Some are smaller and located at popular inns, while others are larger and manned by lifeguards. When you visit the islands, you will see beaches within walking distance of the ferries.

Do I need a car on the Casco Bay Islands?

No, you do not need a car to get around the Casco Bay Islands. It is recommended that you rent a bicycle or golf cart if you plan to explore the islands, but most destinations can be reached by foot.

What’s the best time of year to visit the Casco Bay Islands?

Any time is a great time of year to visit the Casco Bay Islands. The peak season is from May through August. You’ll find that most inns, restaurants, and museums are open only seasonally. For lighter crowds, visit during the off-season.

Are dogs allowed to visit the Casco Bay Islands?

Yes! Dogs are welcome on the Casco Bay Islands. Ferries typically require a ticket to be purchased for dogs.

Littlejohn Island-Casco Bay
Littlejohn Island | photo via brightwell.photo

Plan Your Visit to the Casco Bay Islands

The Casco Bay Islands offer visitors an escape from the hustle and bustle of everyday life. The islands move at a slower pace and offer gorgeous ocean views and a friendly atmosphere.

Located just a short ferry ride from Portland Maine, the Casco Bay Islands are worth a trip, whether for just a day trip or for an extended stay. Since each island has its own special characteristics and personality, it’s best to plan to visit them all.

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