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Chebeague Island Trails

Updated: Aug 24, 2022

Chebeague Island (also known as "Great Chebeague") is located in Casco Bay, 10 miles northeast of Portland. It was originally used as fishing grounds for the Abenaki and is the largest island in Casco Bay that's not connected to the mainland by a bridge. The year-round population was 396 in a 2020 census report and this number is said to triple in the summer months. In 2007, Chebeague succeeded from Cumberland, becoming its own town. This town is made up of 17 islands and their adjacent waters. Here's a map to get a better sense of the location and shape.

The Chebeague & Cumberland Land Trust (CCLT) protects ten properties/trails on Chebeague Island, plus three properties on smaller, surrounding islands. Of these thirteen properties, twelve allow public access. Lucky for me, I now work in membership/outreach for CCLT, so part of my job is to explore them. CCLT has conserved these properties through either purchase or conservation easement (a voluntary, legal agreement between landowner and land trust that permanently limits uses of the land in order to protect its conservation values). My plan is to visit the nine public properties/trails on the main island and share them with you. Not only that, I plan to hide Seek'ems on them. If you're looking for a marathon Seek'em hunt on an island in Maine, you've come to the right place.

Last week I explored five Chebeague trails with a CCLT board member and longtime summer resident. We had a great morning hiding Seek'ems and exploring this gorgeous island. Her son, Wesley Lickus, who spent his childhood summers on this island, created this helpful map of the CCLT properties for us. This will come in handy as you explore, since your GPS is not likely to work on the island. The other challenge is that street signs don't really exists here. This remains a mystery to me, but I've yet to see one. The long and the short is that I'd suggest printing off this map and bringing it with you on your hunt. I can't promise you won't get lost, but this will help.

Before we cover trails and Seek'ems, let's talk about transportation to the island. If I said it was a quick, uncomplicated trip out to Chebeague, I'd be lying. Still, it's worth the adventure and I am going to give you all of the instructions on how to get yourselves over there.

There are two different ferry's for Chebeague: one leaves from Portland and the other from Cousin's Island in Yarmouth. The ferry trip from Portland is 1-1/4 hours and the ferry from Cousin's is fifteen minutes, but does involve a shuttle. Here are instructions for both:

From Cousin's Island: The Chebeague Transportation Company (CTC) provides a ferry from Cousin's, but you'll need to first take a shuttle from their satellite parking lot off of Route 1 in Cumberland. This ferry operates daily with frequent trips throughout the day, so it's highly dependable. For round trip tickets, they charge $18 for adults, $5 for 6-11 year olds and it's free for 5 years and under. But first, you'll need to take a shuttle from CTC’s satellite lot just off Route 1 in the Town of Cumberland (use 1 Thomas Drive, Cumberland Foreside, Maine for your gps. Their parking lot is directly across Route 1 from there). It costs $15 to park in the lot and the shuttle is "free". Passengers travel by shuttle bus to the CTC dock located on Cousin’s Island. The bus leaves the Cumberland parking lot 30 minutes before the ferry arrives at Cousin’s Island. It is a 15-minute ferry ride.

Passengers needing accommodations because of physical disabilities should call the CTC office, 1-207-846-3700, during regular business hours at least 24 hours in advance of travel.

Tickets for this ferry must be purchased online, in advance. When you arrive at the ferry terminal, give them your last name and you'll be in their system. Old school meets new school. All of the info for both the shuttle and ferry can be found here:

It's not cheap and it's not easy, but are you ready for the good news? It's a great experience because you'll meet all kinds of interesting people along the way, get a tour of some great neighborhoods near Cousin's Island and ultimately, end up at a magical place called Chebeague Island.

If you decide to take the ferry from Portland, you'll want to check out Casco Bay Lines:

The schedule is more limited and the ferry ride is much longer, but you'll avoid the shuttle bus. You will also save yourself some money as round trip tickets from Portland are only $11.05 for an adult and $5.50 for a child. Plus, you'll get a longer boat ride out of the deal, if that's appealing to you. As always, choose your adventure and what works best for you.

I've visited Chebeague Island twice now, and have used the Cousin's Island ferry both times, but I'm looking forward to trying the Portland ferry in the fall. A long, peaceful ride on the ocean, coffee in hand...can't wait.

One last idea, you may want to bring a bike. It is a big island and unless you have someone to drive you around, there is a lot of mileage to cover here.

Ok, we've covered the nitty gritty of transportation, let's move on to the good stuff. Here are the five trails we visited last week:


Located in the heart of Chebeague Island, this serene property offers 25 acres of the largest undeveloped forested area remaining on Chebeague. It features critical wildlife habitat; protects Chebeague’s sole source aquifer (underground reservoirs that provide drinking water to islanders); and functions as a stopover point for migratory birds. It also offers trails for recreation including: hiking, cross-country skiing, snowshoeing, fishing, hunting, picnicking, horseback riding, and snowmobiling on designated trails. Find more details and history on these woods here:

The trailhead can be found off of Littlefield Road, across from the Town's public works facility. Look for the new kiosk, which will have a map of this trail.

From the trailhead, follow the trail until you've reached an open area with paths branching out to either side. Have a seat on the bench and enjoy the peace, then continue straight along the path until you've reached a picnic table near a large horse chestnut tree. Look inside the wide branches of the tree to locate our Seek'em.

From here, turn back and follow the path until you've once again reached the intersecting trails near the bench. Take a right and follow this trail until you've reached the farm on your right. Surprise - you've already connected with our next property, Hamilton Durgin Woods.


This 3.3-acre forest was recently protected by CCLT in March of 2021. You can also access these woods by taking the trailhead off of Roy Hill Road, but I'd recommend starting at Littlefield Woods. To find our Seek'em, start at the place where the farm property ends and look down the trail towards Littlefield Woods. Locate the CCLT sign on the tree to your left, then look directly across the path to find the tree shown below. Look around the back side for our yellow Seek'em. Here are more details on Hamilton Durgin Woods:

For the next property, take Littlefield Road until it connects with North Road. Take a left onto North Road and look for the cemetery on your left. You will soon see the historic church on your right and just beyond it, you'll spot this sign for the Curit trailhead.


This quiet property is accessed by a 50-foot wide right of way held by CCLT that runs from North Road across private property. A walking path has been cleared along this right of way to the town-owned land, ending in a loop near the shore that offers tree-framed views of the bay. For details and history on the homestead that was once located here, visit:

To find our Seek'em, follow the path until you've reached the bench near the water, to the left of the ravine. Take a look underneath.

You may be tired at this point, but just keep going and I promise you will not be disappointed. Our next property is a well-used, well-loved spot for islanders.


The public is welcome to use Sanford’s Pond for low impact outdoor recreation including skating, hiking, cross-country skiing, snowshoeing, fishing, hunting, and picnicking. This is a favorite winter skating destination and if you notice the small warming hut to the right of the pond in this picture, you will see where skates, hockey equipment and benches are housed. For pictures of the pond frozen, visit:

There is a mowed path along the perimeter of the pond. Follow this counter clockwise until you've reached the picnic tables on the other side. Look inside the tree to the right of the picnic table to locate our Seek'em.

I've saved my favorite trail for last. It's a great one for summer and offers views of Little Chebeague Island. While I was here, I learned about Little Chebeague...had no idea it even existed, but you can walk over to it at low tide. That is an adventure for my next trip.