Bailey Island

Travel Guide

Bailey Island showing a house and rocky coastline
Bailey Island featuring general coastal views
Bailey Island showing general coastal views
Bailey Island showing signage
Bailey Island showing 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.

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 €109 per night from 24 Aug to 25 Aug
€109
24 Aug - 25 Aug
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! (1,144 reviews)
August 2025
"My daughter and I stayed here for 4 nights while apartment hunting in Portland. We had trouble with our keys working and they finally determined that each time they gave us a different key card, they were authorizing it for just one night. This is an older property but is reasonably well kept. There ..."

Reviewed on 9 Aug 2025

Days Inn by Wyndham Airport/Maine Mall
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
The price is €91 per night from 24 Aug to 25 Aug
€91
24 Aug - 25 Aug
includes taxes & fees
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! (132 reviews)
"Everything from Germaine Inn South Portland is pretty good rooms, facilities, pool etc.. I only whish they provide breakfast until 10AM instead of 9AM."

Reviewed on 11 Aug 2025

Germaine Inn South Portland
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
The price is €123 per night from 1 Sept to 2 Sept
€123
1 Sept - 2 Sept
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! (1,040 reviews)
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Reviewed on 9 Aug 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! (200 reviews)
"We had 3 generations staying in the Friendly Cottage and all of us loved it. The grandkids loved climbing down the rocks to the little beach in front of the cottage and walking to nearby Cedar Beach to swim. My husband, son, and grandson really enjoyed playing golf at Highland Green Golf Club in ..."

Reviewed on 4 Aug 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! (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 24 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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