Bailey Island

Travel Guide

Bailey Island which includes rugged coastline and a house
Bailey Island which includes general coastal views
Bailey Island which includes general coastal views
Bailey Island showing signage
Bailey Island showing a bay or harbor as well as an individual femail

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.

Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
The price is P8,850 per night from Aug 26 to Aug 27
P8,850
P9,791 total
Aug 26 - Aug 27
includes taxes & fees
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
7.8/10 Good! (1,038 reviews)
"The lobby is welcoming. I mean spacious, clean and bright!"

Reviewed on Jul 30, 2025

Clarion Hotel Portland
Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is P6,378 per night from Aug 27 to Aug 28
P6,378
P6,952 total
Aug 27 - Aug 28
includes taxes & fees
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
7.8/10 Good! (1,105 reviews)
"Outside wasn't well kept up. The room was average, clean."

Reviewed on Jul 31, 2025

Days Inn by Wyndham Airport/Maine Mall
Comfort Inn Airport

Comfort Inn Airport

2.5 out of 5
90 Maine Mall Rd, South Portland, ME
The price is P7,800 per night from Sep 1 to Sep 2
P7,800
P8,502 total
Sep 1 - Sep 2
includes taxes & fees
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
8.4/10 Very Good! (1,435 reviews)
"comfortable stay."

Reviewed on Jul 31, 2025

Comfort Inn Airport
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.
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 ...
9.6/10 Exceptional! (68 reviews)
"We had a great stay in the 2 bedroom unit. great set up and was super clean. Loved the proximity to the shopping area and restaurants. Only issue was the front door lock, noticed a lot of the other people were leaving the lock open. Would stay here again"

Reviewed on Jul 24, 2025

The Weldon Hotel
Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor

Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor

3 out of 5
West Boothbay Harbor
Stay at this 3-star beach cottage in West Boothbay Harbor. Enjoy free parking, a garden, and balconies. Popular attractions Juniper Point and Maine State Aquarium ...
Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor
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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