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$145 per night from 20 May to 21 May
S$145
per night
20 May - 21 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 ...
8.6/10 Excellent! (1,456 reviews)
"Friendly staff, clean, and comfortable! Right next to mall area, lots of food, and the highway for easy travel to other destinations in the Portland area! Close to airport too!"

Reviewed on 12 May,2024

Casco Bay Hotel, Ascend Hotel Collection
The Westin Portland Harborview
The Westin Portland Harborview
4 out of 5
157 High St, Portland, ME
The price is S$234 per night from 27 May to 28 May
S$234
per night
27 May - 28 May
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the bar and the helpful staff in ...
8.4/10 Very Good! (1,058 reviews)
"The Westin is very conveniently located in downtown Portland. Great harbor view and wonderful staff."

Reviewed on 4 May,2024

The Westin Portland Harborview
Portland Harbor Hotel
Portland Harbor Hotel
4 out of 5
468 Fore Street, Portland, ME
The price is S$277 per night from 28 May to 29 May
S$277
per night
28 May - 29 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! (1,187 reviews)
The Place to Stay while in Portland, Maine
"The Portland Harbor Hotel has a wonderful, clean, efficient feel. It is right in the center of Fore Street, the center of the "hip, cool, historial" area of Portland. The staff is especially helpful and good-mannered. It has a beautiful garden-courtyard which is a special surprise within a city."

Reviewed on 9 May,2024

Portland Harbor Hotel
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 ...
7.4/10 Good! (31 reviews)
"Like that we can walk to everything we’ll just about, didnt like the construction that was going on at the hotel, no restaurant in hotel and bit small bathrooms but everything else was wonderful"

Reviewed on 29 Apr,2024

Trade Winds on the Bay
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! (171 reviews)
"Hot water was a bit slow to get. It’d take about 5 minutes for the hot water to even start when using the shower. Other than that, this property was very nice. Cute little cottages with everything you’d need for a hiking vacation. The owner was very responsive and nice. Great amenities on the property ..."

Reviewed on 12 May,2024

Hanscom's Motel and Cottages
Village by the Sea
Village by the Sea
3.5 out of 5
1373 Post Rd, Wells, ME
Stay at this 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 attractions ...
8.8/10 Excellent! (436 reviews)
"Large spacious rooms"

Reviewed on 7 May,2024

Village by the Sea
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.

Popular places to visit