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.

Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
The price is €144 per night from 2 Sept to 3 Sept
€144
2 Sept - 3 Sept
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! (1,008 reviews)
"Consistent- we’ve chosen to stay many times both when we need Park and Fly and when going to local concerts at Thompson Point so we can walk over, and have the long drive home late at night. Clean, friendly and convenient. Price is reasonable."

Reviewed on 23 Aug 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 €100 per night from 27 Aug to 28 Aug
€100
27 Aug - 28 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! (1,246 reviews)
"Friendly staff"

Reviewed on 25 Aug 2025

Days Inn by Wyndham Airport/Maine Mall
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
The price is €120 per night from 2 Sept to 3 Sept
€120
2 Sept - 3 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 ...
7.8/10 Good! (1,050 reviews)
"Great"

Reviewed on 24 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! (202 reviews)
"Lovely home with wonderful view of the ocean. The house is in the side yard of the owner’s main house but it feels separate and private. We enjoyed outings in the area during the day and cooked dinners in the well equipped kitchen at night. Owners are helpful and responsive. Highly recommend for ..."

Reviewed on 16 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! (73 reviews)
"nice building walkable to shopping + dining"

Reviewed on 22 Aug 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 ...
Perfect for a long weekend
"The property was as described, clean, and in a quiet neighborhood. Conveniently located to many local attractions. Check in and check out process was smooth. Overall enjoyed my stay very much."

Reviewed on 23 Jun 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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