How to Spend A Day in Chebeague Island, Maine’s Smallest Island? (2024)

Maine is home to more than 1000 Islands, and Chebeague Island is the smallest amongst them all. Nestled in Casco Bay, an inlet of the Gulf of Maine, Chebeague Island is the newest in Maine but has its fair share of popularity. This little-known Charming Island is home to generations of summer and year-round residents. It is also high on tourism, but still, the place never gets crowded. Mainers often choose Chebeague for a peaceful weekend getaway or some alone couple time.

Chebeague Island in English translates as “isle of many springs.” A true Maine gem, this little Island is where people visit for solace and life that is less complicated. Being here hits the reset button from life’s hustle and bustle. Chebeague (which is pronounced as sha-big) is safe, soothing, and extremely welcoming. Visitors might not find a range of ‘Touristy’ things to do, but some good enough options to make a vacation. Chebeague Island is just off Portland and, therefore, quite easy to reach. So ready to be here?

How to Spend A Day in Chebeague Island, Maine’s Smallest Island?

Popular Things To Do On Chebeague Island On A Day-Trip

Chebeague Island is really small, and that’s why a day here is always enough. Most of the activities on the Island are walkable and easy to traverse. However, one should bring a paper map for easy navigation through the place.

1. Deer Point

Located at the southwestern tip of Chebeague, Deer Point is one unique feature of the Island. This picturesque rocky point with a blue ocean, rock ledges, and dark pine trees is a sight to be seen. Locals and visitors often choose Deer Point for afternoon picnics and nature walks. Finding sea glasses on the beach is one of the popular activities here.

Deer Point is also an inspiration for artists and photographers.

2. Little Chebeague at “The Hook.”

The Hook is a popular point of attraction on Chebeague Island during the low tide days. One can walk across the sandbar and reach the Little Chebeague since low tide exposes the sand. Whereas on normal days, Little Chebeague is only accessible via a boat ride. Little Chebeague isn’t inhabited, but it has an abundance of nature and ruins of abundant houses. The area is also a popular spot for camping. However, if you are walking to Little Chebeague island, make sure to come back before high tide, or you will be trapped.

3. Hamilton Beach

Hamilton Beach is undoubtedly the most popular tourist attraction on Chebeague Island. This beautiful sandy beach spread is an ideal spot if you are looking for a peaceful day at the seaside. The water on this side of the ocean is definitely warmer and thus ideal for dipping and swimming. However, as there are no lifeguards on duty, novice swimmers should keep themselves on the safer side. Hamilton Beach is also popular for finding seagrass and other sea and sand treasures. During night hours, a beach is a fine place for bonfires, BBQ, and star gazing.

4. Chandler’s Wharf Fishing

Chandler’s Wharf is the go-to place on Chebeague Island for locals and visitors alike. It is where people socialize, chat, catch squid and, most popularly, try their fishing skills. The Wharf is right where the Casco Bay Lines ferry comes and thus is always full of people. During day hours, fishing and swimming are some popular activities here. Whereas during the night, this site is known amongst young party seekers.

5. Biking and Cycling

Chebeague Island is just 3 miles wide and 5 miles long and thus best explored on cycles and bikes. Even the least accessible beaches and secluded portions of the Island are reachable via cycles. Since cycling is a popular activity at Chebeague Island, there are a few dedicated service providers. For instance, Summer Feet Cycling offers affordable guided bike tours. These tours take participants to different locations, including a general store with 50-cent coffee, still-operating one-room schoolhouses, and more insides of island life.

Biking and cycling from Chebeague Island’s end to end is an experience on its own. If you aren’t up for tours, you can bring your own cycle by loading it into the watercraft.

While cycling through the Island, you will come across historic churches, wild purple lupines fields, estates fronted by manicured lawns, and Cape- and Victorian-style homes. All of these features offer some excellent photographing opportunities.

6. Great Chebeague Golf Course

Last but one of the most appealing things to do on Chebeague Island is play a game of golf at Great Chebeague Golf Course. This country club facility features a nine-hole golf course nestled on a 28 acres landscape on Chebeague’s north. Enjoying a game of golf here with a splendid view of the ocean is definitely an experience to live. What’s even better is that one of the holes is separated by the ocean, and finding it is no less than an exciting adventure.

The Great Chebeague Golf Course is also home to a repurposed circa 1807 clubhouse. It, in fact, is one of the oldest buildings used for that purpose in the United States.

How to Reach Chebeague Island?

Getting there to Maine’s smallest Island is quite convenient. Chebeague Island can be reached via a few different options:

• Diver north of Portland, right towards Yarmouth. Park your car in a remote lot on Route 1. Next, take the old school bus, and it will navigate you to the local Ferry terminal.
• From there, hop for a ferry ride into Casco Bay and out to the Chebeague Island Inn. The enjoyable and relaxing ferry ride is nearly 20 minutes long, and ferries are fun and quite frequent.
• Or, reach Chebeague Island through Casco Bay Lines though it will take an hour. Casco Bay line operates a Mail Boat that runs thrice a day. It picks and drops at designated stops. Individuals who want to enjoy the breathtaking views of the different islands in Casco Bay can opt for the second option.
• Portland Express Water Taxi or Island Water Taxi operating from Portland are other great options, but they are definitely the expensive ones.

What Is The Best Time To Visit Chebeague Island? 

Chebeague Island is a summer destination, and therefore June through October is the best time to be here. It is when the temperature is enjoyable, and one can indulge in a range of seaside opportunities. Also, summers being the peak season, offer more convenience from a ‘Tourist’ point of view.

Where to Stay When on Chebeague Island?

Even though a day trip to Chebeague Island is more than enough, for people who want to stay back, the Chebeague Island Inn is an excellent option. There are several reasons visitors would want to spend a night here. Dating back its history of 1880, this property features the widest and most inviting porches on the Atlantic. Sipping a cup of hot coffee or a mug of chilled beer here is what everyone dreams of. Chebeague Island Inn has 21 guest rooms, a 75-seat fine-dining restaurant overlooking the sunset, and a Great Room with a large stone fireplace. The classic beauty and hospitality here are definitely enjoyable.