Things to Do:

Explore the island by bike — The best way to see Chebeague is on two wheels! The Chebeague Island Inn has beach cruiser bikes available for guests, making it easy to cruise the quiet island roads, explore the different neighborhoods, and stop at the beaches along the way.

Spend the day at Hamilton Beach — Just a short walk from the Inn, Hamilton Beach is a great spot to relax, swim, read, or enjoy a picnic. The Inn provides beach chairs, towels, and

umbrellas for guests.

Walk out to The Hook — Head to Indian Point, known locally as “The Hook,” for beautiful views of Casco Bay. At low tide, you can walk across the sandbar toward Little Chebeague Island for a fun little adventure. Be sure to check the tides before heading out!

Play a round of golf at Great Chebeague Golf Club — Located right next to the Inn, this nine-hole links-style course has incredible ocean views from every hole. It’s a perfect way to spend a leisurely afternoon on the island.

Play a match at the Great Chebeague Tennis Club — Grab a racket and head over to the Great Chebeague Tennis Club for a friendly game of tennis. It’s a fun way to get some exercise while enjoying the relaxed island atmosphere.

Take a dip at the Chebeague Recreation Center — Head to the Chebeague Recreation Center for a swim in the island’s community pool. It’s a great option for cooling off on a warm summer day or for families looking for a fun place to

spend an afternoon.

Play lawn games at the Inn — Challenge your friends to a game of bocce, cornhole, croquet, or frisbee on the Inn’s lawn. Or, after the sun goes down, gather around

the fire pit for s’mores.

Take a boat out on Casco Bay — Arrange a private boat charter to explore Chebeague and the surrounding islands, or spend the day out on the water taking in the coastline, wildlife, and beautiful views of Casco Bay.

Visit Little Chebeague Island — For a little adventure, head across to Little Chebeague at low tide from The Hook. The island is undeveloped and offers a more rugged, natural side of the Maine coast.

Visit the Chebeague Island Historical Society — Learn a little about the island’s history and explore its collection of photographs, artifacts, and exhibits. It’s a great stop for anyone interested in the history of this special little community.

Do absolutely nothing! — One of the best things about Chebeague is slowing down. Grab a book, sit on the porch, walk to the beach, and enjoy a little island time.

Favorite Eats:

Chebeague Island Inn — Obviously our first choice! Grab a cocktail, enjoy a meal overlooking Casco Bay, or settle in on the porch for a drink and take in the views.

The Niblic — a great island stop for coffee, breakfast, sandwiches, salads, chowder, baked goods, ice cream, and snacks. They also have a cute selection of Chebeague clothing, gifts, and souvenirs. Grab your food to go or enjoy it on their scenic deck overlooking the water.

The Slow Bell Cafe — a casual island restaurant and bar near the center of Chebeague. A great spot for dinner, drinks, soft serve, and often live music. Check their hours before heading over, as they vary throughout the season.

Things to Do:

Take the ferry to Peaks Island- walk around or rent a bike

Go shopping at the local retail stores in downtown Portland (commercial street) or outlet shopping in Freeport (where the flagship L.L Bean store is located and where you can take photos by the giant bean boot)

Walk, run, rent a kayak or have a picnic at the eastern promenade, a two mile path with great views of the Casco Bay, beach access, a playground and food trucks

Check out Maine's oldest bookstore - Sherman's Maine Coast Book Shop which was founded in 1886, or other Portland book stores, Longfellow Books, Green Hand Bookshop or Back Cove Books

For hiking you can visit Popham Beach State Park, Bradbury Mountain State Park, Wolfe’s Neck State Park. If you're looking to extend your stay, we highly encourage making a trip to Acadia National Park!

Check out the Portland Museum of Art

Visit the Portland Headlight and Fort Williams Park

Favorite Eats:

Taco Trio - the best tacos in town!

Kettle Cove Ice Cream - a quaint little stop with incredible ice cream

C Salt - a favorite stop with a little bit of everything!

Scratch Bakery - if venturing over during the weekend, make sure you get there early. Their bagels alone are worth the trip! Feel free to grab a coffee and head to Willard Beach for a stroll.

Porthole - great spot to catch some live music on Portland's largest dock

Duckfat - make sure to get a milkshakes and the poutine, and you can't go wrong with any of their sandwiches. You can also visit with Frite Shack at Oxbow Brewery for just fries and less of a line

Eventide - famous lobster rolls and seafood

Honey Paw - sister restaurant to Eventide that serves amazing Southeast Asian food

Bread and Friends - fun coffee and brunch spot

High Roller Lobster Co - amazing lobster rolls

Solo Italiano - upscale Italian food

Scales - upscale seafood restaurant right on the water

Leeward - another great Italian restaurant

Twelve - new popular dinner spot

Rose foods - delicious bagels

The Ugly Duckling - pastries, breakfast sandwiches and coffee

Izayaka Minato - great Japanese food

Fore Street - one of the most popular restaurants in Portland

Standard Baking Co - a must do and worth the long wait for their famous pastries (they're all amazing)

Tandem Coffee Co - excellent coffee shop

The Holy Donut - delicious and unique donuts

Portland has tons of amazing breweries that we love to visit, here are a few of our favorites:

Bissell Brothers

Belleflower

Definitive

Oxbow

Austin St

Rising Tide

Allagash

Batson River Brewing