Things To Do
Golfing
The Great Chebeague Golf Course is a nine-hole course with a view of the ocean from every hole. Tee times not required but recommended for large groups (looking at you Fialas).
Trails
Explore the island's beautiful beaches and trails, like Hamilton Beach or Rose's Point. During low tide, you can walk across a sandbar to Little Chebeague Island.
Chebeague Island Inn
The restaurant at the inn is the best place to get a sit-down meal on the island. Come by for breakfast, lunch or dinner, or just to see your favorite people.
Two Birds Café
A lovely spot for breakfast, lunch, coffee or pastries. Open every day until 3:00.
Doughty's Island Market
Stock up on wine, beer, and essential groceries for the weekend or get your morning iced coffee fix.
Boat Tours
The best way to see Casco Bay! Go whale watching or catch your own lobsters. There are several tour companies that operate from Portland. Bring layers!
Freeport
Famous for its outlet shopping! If you're staying in Freeport, check out the shops and restaurants at the Freeport Village Station. And if you're into camping, hunting, or fishing at all, check out the flagship L.L. Bean store. Also worth visiting is the Maine Beer Company brewery. We love the "Lunch" beer.
Old Port
Historic neighborhood in downtown Portland. You can spend an entire day wandering the cobblestone streets but here are a few of our favorite spots. Duckfat Blyth & Burrows Eventide Honeypaw Fore Street Scales The Holy Donut The Gelato Fiasco Mt. Desert Island Ice Cream
Allagash Brewing Co. & Bite Into Maine
Home to everyone's favorite Belgian-style wheat beer and the best lobster rolls in Portland. A lot of people will tell you where to find the best lobster rolls, but these are it. Would we lie to you? Don't answer that.
Portland Head Light
The oldest lighthouse in Maine and most photographed lighthouse in the US! As if that weren't reason enough to visit, there's ANOTHER Bite Into Maine here.