Bailey Island Travel Guide

Tourist Guide

Bailey Island which includes a house and rocky coastline
Bailey Island featuring general coastal views
Bailey Island featuring general coastal views
Bailey Island featuring signage
Bailey Island which includes a bay or harbour as well as an individual female

Try to resist marooning yourself forever on this serene bit of land that features beaches, hikes and a lively community.

Bailey Island is prototypical Maine, with rocky beaches, gruff lobster fishermen and small-town charm that epitomize the Pine Tree State. First settled by the son of a freed slave, William Black, the island is named after Reverend Thomas Bailey. Look down when driving over the Bailey Island Bridge to spot Will’s Gut, the spit separating Orr’s Island and Bailey Island and named for its original inhabitant.

Pause at the opposite side of the bridge for a look at the bridge itself, a nationally recognised historic landmark, a rare cribstone bridge that allows the tides to pass through its structure. Drive to Mackerel Cove for the picture-postcard Maine settlement with small houses and lobster fishing boats bobbing on the edge of Casco Bay. Continue to the end of the island, Land’s End, and let the spray cool you down in the warmer months as you gaze across the sea. Buoys bobbing in the water indicate locations of lobster cages.

Hike along the short Giant’s Stairs Trail to learn about the varied geology of Bailey Island. Climb down huge black stones, so different from surrounding rocks, and look for flecks of garnet and quartz.

Bailey Island is part of Harpswell, with a town council governed by popular vote, creating a strong sense of community. Bailey Island’s community centre and main event space is the Bailey Island Library Hall. Stop by for an event or simply to see this historic building where the famous psychoanalyst Carl Jung gave an early American lecture.

Drive to Bailey Island in 1 hour from Portland, Maine. Boat tours from Portland also occasionally come out to Harpswell and its more than 200 islands. Portland has an international airport serving numerous locations and is just 90 minutes by car from Boston. Harspwell does not have public transportation, so rent or bring a car.

Bailey Island is the perfect place for a Maine getaway, whether you are locals, frequent visitors or have never been to this beautiful part of the world.

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Bailey Island
Book a stay at this beach vacation home in Bailey Island. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Cobwork Bridge and Mackerel Cove ...
10/10 Exceptional! (208 reviews)
"This was an incredible place to stay! The hosts were the best we have had to interact with. The area was full of things to do. We played golf at the Sebasco Resort twice during our stay. You can’t beat getting lobsters at Watson’s General Store on Cundy’s Harbor. The Friendly Cottage had all we needed ..."

Reviewed on 8 Oct 2025

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street, Portland, ME
The price is AU$279 per night from 2 Nov to 3 Nov
AU$279
per night
2 Nov - 3 Nov
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the bar and the ...
9.2/10 Wonderful! (1,611 reviews)
"The parking was easy and very secure. The attendants were the best! The room was exquisite, and the coffee, tea, pastry, etc bars on each floor were so nice. All seating areas and the restaurant offered everything we could want. Very welcoming and helpful staff."

Reviewed on 12 Oct 2025

Portland Harbor Hotel
Germaine Inn South Portland

Germaine Inn South Portland

2 out of 5
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
The price is AU$151 per night from 30 Oct to 31 Oct
AU$151
per night
30 Oct - 31 Oct
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maine Mall and Thompson's ...
7.4/10 Good! (315 reviews)
"Super friendly staff, clean, comfortable and conveniently located! The breakfast was especially good and the staff couldn't have been friendlier! I would absolutely go back!"

Reviewed on 13 Oct 2025

Germaine Inn South Portland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Bailey Island
Book a stay at this beach vacation home in Bailey Island. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Cobwork Bridge and Mackerel Cove ...
10/10 Exceptional! (208 reviews)
"This was an incredible place to stay! The hosts were the best we have had to interact with. The area was full of things to do. We played golf at the Sebasco Resort twice during our stay. You can’t beat getting lobsters at Watson’s General Store on Cundy’s Harbor. The Friendly Cottage had all we needed ..."

Reviewed on 8 Oct 2025

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
54 York St, Portland, ME
Stay at this 4.5-star luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Thompson's Point ...
9.8/10 Exceptional! (82 reviews)
"Great spot, large space, cool design, clean, easy to walk all over town."

Reviewed on 1 Oct 2025

The Weldon Hotel
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

2 out of 5
Portland
Book a stay at this golf vacation home in Portland. Enjoy free WiFi, a beach locale, and in-room fireplaces. Popular attractions Thompson's Point and Maine Mall ...
10/10 Exceptional! (3 reviews)
"We have our own vacation rentals so I know the challenges. I would suggest a single serve coffee maker. Easy to care for provides far better coffee and options for coffee flavors in the “pods”. Instant coffee is just not good… Great place. Loved the steamer! Thanks for the snacks!"

Reviewed on 28 Sept 2025

Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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