Posted on November 12, 2022 and last updated on August 01, 2023

Chebeague Island, Casco Bay


  • Preserve Size: Varies
  • Trail Mileage: Varies
  • Pets: yes
  • Difficulty: easy to moderate
  • Sights: Ocean vistas, sandy beaches, neighboring islands

Map is incomplete, especially the trails on Little Chebeague Island.

Chebeague Island is the largest in Casco Bay; it’s almost five miles long and 1.5 mile wide. Though there aren’t big preserves here with extensive trail networks (with the exception of Little Chebeague), the island is a wonderful place to visit and do a bit of walking.

Not only is it beautiful, with white sandy beaches and rocky outcrops, the whole island has a welcoming feel. Drivers follow that Maine island tradition of waving to everyone they pass. And I saw very few Posted or No Trespassing signs. In fact, more often you’re likely to see a little white sign by the side of the main road that reads, “Right of Way to Shore.”

A few trail descriptions below: (I’m only including pmes I know are protected — mostly by the Chebeague and Cumberland Land Trust. There are more trails on the island than listed here. I’ll post them as I walk them!

Note: If you are only doing a day trip to the island, bring your bicycle! Parking is not easy at some of the trailheads, and with few cars on the roads, the island is easy to get around. But at least one trail, Deer Point, has a sign requesting people leave their bikes at the trail head and proceed on foot.)

  • Little Chebeague, from Indian Point, aka the Hook — If you’re hitting the sandbar at low tide, you can walk from the Hook to the 100-acre island, an amazing place to explore with about 1.2 miles of trails in its network. The island is protected by Maine Island Trail Association and Maine Bureau of Parks and Lands. The island has informational kiosks and even a seasonal caretaker.
    Wide, grassy trails cut through the low brush, bringing you to beaches, campsites, and historical sites. Much of the walking is easy and flat. I ran out of time during my visit to walk them all, so will be back soon I hope. 
    If you’re crossing the sandbar, which is approximately a quarter-mile, keep your eye on the time and make sure you give yourself lots of time to cross before the tide comes in. Walking on the sand and pebbles of the sandbar will be slower going than normal. If you budget two hours before and after high tide for your walk, you should be safe. 
    Indian Point, itself, is a protected 16 acres shaped in a hook, with a “windswept wildness.” The western-facing portion of the beach is private, and unauthorized vehicles are not allowed on the narrow gravel access road.
    Directions: You’ll find the gravel access road to The Hook off Cottage Road, at the southwest corner of the island, right as the road bends. Indian Point, 16 acres. Little Chebeague, 100 acres.
  • Deer Point — At the southeastern corner of the island, you can leave your bikes at the start of a dirt lane and walk 0.6 miles by a few houses to a rocky outcrop with beautiful views of Little Chebeague, Long Island, Hope and Cliff Islands. The driveways narrows to a rocky, rougher footpath near the end, and when we visited, went by many downed trees.
    Along the way, you won’t see many trail blazes, but as long as you continue on the track and head straight to the ocean, you will not get lost. Near the official sign at the start of the trail is a home-made sign asking people to please leave their bicycles behind. You also can’t park at the trailhead if you have a car. 
    Directions: From South Road, turn onto Western Landing Road. You’ll turn onto a rutted dirt road and head up a short hill. Follow the road as it curves to the right. A sign on your right will indicate Deer Point lies ahead. 13 acres, 0.6 miles one way. Park along South Road near Bennett’s Cove.
  • Sanders Pond —A destination for skating in the winter, you can make a tiny walk around three-quarters of the pond if you wish. You’ll find the pond off Chandlers Cove Road, it’s marked with a kiosk by the side of the road. 1.8 acres, 0.1 mile one way
  • Curit Trail — Across North Road from Chebeague Island Cemetery, you will find a short, well-blazed walk in the woods to a bench overlooking a forested bank, a ravine, and the bay through a screen of trees. 8.2 acres, 0.8 miles
  • Gray Path — A very short but charming path with a boardwalk and staircase that’s really more a pedestrian access to a small, beautiful beach. Part of the path crosses private property. It’s on the west side of South Road, right before the road split into Willow Street and Avon  Street. 1.2 acres, 0.1 mile one way
  • Littlefield and Hamilton-Durgin Woods — The best part of this conserved tract of forest for a human visitor is the open grove at the end of a trail, which has a picnic table under a gigantic chestnut tree. The preserve contains old trails that once linked former farms and helps protect the island’s aquifer used for drinking water.
    Directions: To get to the grove, start at the trailhead kiosk on Littlefield Road, right across the street from the Chebeague Island Transfer Station. Walk straight until you reach the four-way intersection, another kiosk, and a granite bench. Continue straight here. 24 acres, 0.5 miles in network

Directions to the island: There are two ferries to Chebeague: the CTC ferry that leaves from Cousins Island in Yarmouth and takes 15 minutes (but add in the time it’ll take to get to the wharf, since you have to take a shuttle or bike there), and a much longer Casco Bay Lines ferry from Portland that takes 60-90 minutes one way. There is no parking at the ferry dock at Cousins Island, so the company maintains a satellite parking lot off Route 1 and runs a shuttle bus back and forth. The ride takes about 12 minutes, and the bus accommodates bicycles. The bus price is included in the price of the ferry ticket…but they also charge a hefty fee if you want to leave your car in the lot ($15/day in 2022). If you have a bicycle, perhaps leave your car somewhere else nearby and ride down to the dock? The address is 178 Wharf Road.

Let me know if you have any trail updates or corrections!