The quickest option is the Chebeague Transportation Company, which runs a ferry every couple of hours out of Yarmouth, early morning through evening (park at 1 Thomas Dr., Cumberland Foreside; 207-846-3700). Parking is in a satellite lot, and a bus connects to the dock before every departure. From the parking lot to the north side of the island, near the Chebeague Island Inn, the trip is all of about 30 minutes. Casco Bay Lines services the more scenic route, with an hour-plus ride from Portland more than half a dozen times per day (56 Commercial St.; 207-774-7871). The boat stops at other islands along the way, eventually arriving at Chebeague’s southern end. Buy tickets ahead for Chebeague Transportation Company or in-person for Casco Bay Lines — round trips are $18 and $11, respectively.
The best way to see the island is on two wheels. If you own a bike, bring it along — the only loaners available are for guests of the Chebeague Island Inn, and bringing a bike on the ferry costs just a few extra bucks. Cruise around the quiet island roads, stop at Hamilton Beach (17 Willow St.) for a bracing dip, and take in the many ocean vistas. The island is plenty walkable too, but it’s more than three miles long, north to south. That’s a lot of ground to cover, especially if adding in the low-tide-only jaunt across a sandbar to neighboring Little Chebeague, where 1.2 miles of trails traverse woods, beach, and an abandoned summer colony (access from Indian Point Rd.). For some island history, visit the agricultural museum at Second Wind Farm, in an old timber-frame barn — and buy some fresh produce from the stand (on Roy Hill Rd.). Or, if another type of greens is more your speed, play the nine holes at Great Chebeague Golf Club (16 Stone Wharf Rd.; 207-846-9478). The seventh is a short shot from one side of a cove to the other. Should be easy, right?
Eat & Drink
There’s no going wrong with either old standby The Niblic (24 Niblic Cir.; 207-846-1015) or newcomer Two Birds Café(412 North Rd.) for hearty sandwiches, baked goods, or coffee. For a full-service breakfast, lunch, or dinner, stop by the mod-meets-classic dining room of the 19th-century Chebeague Island Inn (61 South Rd.; 207-846-5155). From grits with oyster gravy in the morning to mussels in spicy sambal in the afternoon to butter-basted cod with rapini and salsa verde in the evening, the menus are interesting all day long. At sunset, enjoy a drink on the westward-facing porch.
Apart from a handful of short-term vacation rentals around the island, the Chebeague Island Inn is the only show in town. Luckily, it’s a good one. Its shuttle will pick up guests at either ferry landing. And from the porch’s sweeping sunset views to the lobby’s towering fieldstone fireplace to the historic but light and bright rooms, the place is cozy and grand at the same time.