Bailey Island

Travel Guide
Bailey Island showing general coastal views
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.

Casco Bay Hotel, Ascend Hotel Collection
Casco Bay Hotel, Ascend Hotel Collection
3.5 out of 5
80 John Roberts Rd., South Portland, ME
Fully refundableReserve now, pay when you stay
The price is S$131 per night from 30 May to 31 May
S$131
per night
30 May - 31 May
Stay at this 3.5-star business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
8.4/10 Very Good! (1,501 reviews)
"Clean and convenient location. Bed comfortable. Eggs at breakfast were cold - make your own waffles were good . Basic accommodations, would stay again."

Reviewed on 23 May,2024

Casco Bay Hotel, Ascend Hotel Collection
Portland Harbor Hotel
Portland Harbor Hotel
4 out of 5
468 Fore Street, Portland, ME
The price is S$395 per night from 29 May to 30 May
S$395
per night
29 May - 30 May
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the breakfast and ...
9/10 Wonderful! (1,194 reviews)
"The hotel was very comfortable and the staff was friendly and helpful."

Reviewed on 23 May,2024

Portland Harbor Hotel
Canopy by Hilton Portland Waterfront
Canopy by Hilton Portland Waterfront
4 out of 5
9 Center Street, Portland, ME
The price is S$377 per night from 29 May to 30 May
S$377
per night
29 May - 30 May
Stay at this 4-star hotel in Portland. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the restaurant in our reviews. ...
9.2/10 Wonderful! (648 reviews)
"Great hotel in a good location along the waterfront. The rooms were lovely, and the rooftop bar is great."

Reviewed on 21 May,2024

Canopy by Hilton Portland Waterfront
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.
Trade Winds on the Bay
Trade Winds on the Bay
3 out of 5
2 Park Dr, Rockland, ME
Stay at this 3-star aparthotel in Rockland. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Project Puffin Visitor Center and Maine ...
7.6/10 Good! (40 reviews)
"This property is centrally located in Rockland and within walking distance to the harbor, dining, coffee, shopping, and more. We had a great harbor view from our room. And while Trade Winds is old and needs work (smells old and we had to air out our room every time we came back to it.), it's in the ..."

Reviewed on 23 May,2024

Trade Winds on the Bay
Village by the Sea
Village by the Sea
3.5 out of 5
1373 Post Rd, Wells, ME
Stay at this 3.5-star condo in Wells. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the clean rooms in our reviews. Popular ...
8.8/10 Excellent! (446 reviews)
"Large spacious rooms"

Reviewed on 7 May,2024

Village by the Sea
Hanscom's Motel and Cottages
Hanscom's Motel and Cottages
3 out of 5
273 ME-3, Bar Harbor, ME
Stay at this 3-star cottage in Bar Harbor. Enjoy free WiFi, free parking, and a garden. Our guests praise the clean rooms in our reviews. Popular attractions ...
9/10 Wonderful! (172 reviews)
"Liked the outdoor seating options. The Location was a short drive into town."

Reviewed on 20 May,2024

Hanscom's Motel and Cottages
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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