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 recognized 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 center 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.

The Westin Portland Harborview
The Westin Portland Harborview
4 out of 5
157 High St, Portland, ME
The price is AU$231 per night from 20 Apr to 21 Apr
AU$231
includes taxes & fees
20 Apr - 21 Apr
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the bar and the helpful staff in ...
8.8/10 Excellent! (1,002 reviews)
"Great staff and facility."

Reviewed on 9 Apr. 2025

The Westin Portland Harborview
Portland Harbor Hotel
Portland Harbor Hotel
4 out of 5
468 Fore Street, Portland, ME
The price is AU$327 per night from 20 Apr to 21 Apr
AU$327
includes taxes & fees
20 Apr - 21 Apr
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 ...
9/10 Wonderful! (1,482 reviews)
Wonderful anniversary weekend
"We visited for a long weekend to celebrate our anniversary. Everything was amazing. Staff was courteous and friendly. We ate at many of the areas fine dining establishments but had breakfast each day at the hotel and ended each night with drinks and dessert at the bar. We will definitely be back ..."

Reviewed on 13 Apr. 2025

Portland Harbor Hotel
Cambria Hotel Portland Downtown-Old Port
Cambria Hotel Portland Downtown-Old Port
3 out of 5
25 HANCOCK STREET, Portland, ME
The price is AU$264 per night from 22 Apr to 23 Apr
AU$264
includes taxes & fees
22 Apr - 23 Apr
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant ...
9.2/10 Wonderful! (843 reviews)
"So far we love everything! The 4th floor lounge is a great amenity when your family is taking up too much space in the room. Welcoming fire place and kind staff. I’ll see what the beds are like shortly."

Reviewed on 14 Apr. 2025

Cambria Hotel Portland Downtown-Old Port
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.
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
Bailey Island
Stay at this cottage in Bailey Island. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Cobwork Bridge and Bailey Island ...
9.2/10 Wonderful! (10 reviews)
Spectacular views
"Loved the location."

Reviewed on 23 Jul. 2024

Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Bailey Island
Book a stay at this family-friendly vacation home in Bailey Island. Enjoy free WiFi, a garden, and patios. Popular attractions Bailey Island Bridge and Cobwork ...
9.6/10 Exceptional! (53 reviews)
Comfortable
"Great house very comfortable and well appointed. Very roomy for our entire family. Nice to have en suite bathrooms with all the bedrooms. The host was very good with communication. Located on a busy road and the driveway is on a curve which made it a little challenging entering and exiting the ..."

Reviewed on 8 Sep. 2024

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
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 Bailey Island ...
10/10 Exceptional! (190 reviews)
Magical and Quaint with Thoughtful Hosts
"We had a peaceful time at this home. It served as a home base for exploring. When my daughter left her most priced possession, her stuffed otter, the lovely hosts found it and shipped it back to us. We're so grateful for the thoughtfulness."

Reviewed on 27 Oct. 2024

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