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.

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
The price is NZ$230 per night from 24 July to 25 July
NZ$230
24 July - 25 July
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! (1,046 reviews)
"Everything was amazing the only thing I didn’t care for is that the person working in breakfast would just bust through people instead of using his words!"

Reviewed on 21 Jul. 2025

Days Inn by Wyndham Airport/Maine Mall
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
The price is NZ$280 per night from 11 Aug to 12 Aug
NZ$280
11 Aug - 12 Aug
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! (1,013 reviews)
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Reviewed on 19 Jul. 2025

Clarion Hotel Portland
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is NZ$285 per night from 28 July to 29 July
NZ$285
28 July - 29 July
includes taxes & fees
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, free parking, and 2 hot tubs. Our guests praise the restaurant and the helpful staff ...
7.6/10 Good! (1,044 reviews)
"Staff was wonderful!"

Reviewed on 20 Jul. 2025

Ramada Plaza by Wyndham 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! (198 reviews)
"Tremendous stay, great property and host."

Reviewed on 13 Jul. 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 ...
9.6/10 Exceptional! (67 reviews)
"It was a large space, basically a one bedroom apartment with a full kitchen, island with bar stools, dining area, living area with a huge TV, and a small bedroom that just fit a king sized bed, small bedside tables, and a closet. Nice bathroom. Very clean and modern. Only missing a full-length mirror ..."

Reviewed on 17 Jul. 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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