This is much of what I love about Maine. The rugged wilderness. The untamed Atlantic. A string of islands close to Harpswell’s shore made of shoal and sediment and sand—and perfumed by wild roses that somehow manage to take root. So, it should come as no surprise that the charming, ocean-swept Bailey’s Island makes an extraordinary destination. Learn why you might want to plan a day trip (or longer) to Bailey Island Maine with a visit to scenic “Land’s End,” too.
CONTENTS: In this article, you will learn everything you need to know about planning a trip to Bailey Island Maine, including:
- Where is Bailey Island, Maine?
- History of Bailey Island
- How to Get to Bailey Island Maine
- What to See and Do on Bailey Island, Maine
- What is Land’s End in Harpswell ME
- Where to Park at Land’s End
- Exploring Land’s End in Harpswell
- A Must-See: The Land’s End Gift Shop
- Best Time to Visit Land’s End
- The Land’s End Beach
- Casco Bay Lines & Tours
- Where to Stay on Bailey Island
- Final Thoughts
My mother and I, along with my college-age son, took a road trip to Maine. We spent the better part of an afternoon exploring Bailey Island in Harpswell before meeting friends for dinner. We could have lingered much longer.
Bailey Island makes for a great scenic road trip in itself or combined with other stops along a longer scenic Maine drive. It’s also an excellent destination for inflatable kayaks and all sorts of other outdoor activities.
As with many coastal towns on the rugged Maine Coastline, you can expect to find beautiful scenery, quaint New England fishing communities, and an independent way of life.
The region is home to some of the few remaining working harbors on the Maine coast.
Related Article: Travel further inland to discover picturesque Bethel, Maine.
Where is Bailey Island Maine
You’ll find Bailey Island in the Greater Portland and Casco Bay region of Maine. It’s about an hour-and-a-half drive (50 miles) from Portland, and 15 miles south of Brunswick, Maine. From Boston, it’s 140 miles by car.
Bailey Island is one of three islands–Bailey Island, Orrs Island, and Sebascodegan or “Great Island”–each connected to the mainland by bridge. They make up the town of Harpswell. More specifically, Bailey Island is part of the 216 miles of rocky coastline that comprises Harpswell Neck.
It’s also the last stop on Route 24.
History of Bailey Island
Known a “Newaggin” when settled in the 1600s, Bailey Island is the smallest of the three islands; a charming coastal town in New England with a year-round population of just 400. (Source: 2000 Census).
The island is named for Deacon Timothy Bailey of Massachusetts, who is said to have bought the island in 1750 for 1 pound of tobacco and 1 gallon of rum and named the island for himself.
How to Get to Bailey Island Maine
There are two ways to get to Bailey island: by land or by sea. In order to get there from the mainland, you must travel Route 24 across the Cribstone Bridge, which is the only one of its kind in the world.
Related: Before you hit the road, be sure you consider the pros and cons of traveling by car.
Crossing The Cribstone Bridge
Built in 1927, the narrow Cribstone Bridge is made entirely of large stacked granite blocks, connecting the islands of Bailey Island and Orr’s Island in the town of Harpswell.
The bridge is a historic civil engineering landmark, listed on the National Register of Historic Places.
It’s 1,122 feet long and the blocks are held together by gravity alone. This unique design allows water to flow freely through the open cells without disturbing the structure as the tide changes.
We pulled over in the dirt lot to the right before crossing to take some photos and to watch the boats gracing the waterway.
If you’re looking for a bite to eat overlooking the water, Cook’s Lobster & Ale House is right around the corner from the bridge.
How to Get to Bailey Island Maine by Sea
The other way to get to Bailey Island is by sea.
Casco Bay Lines offers scenic tours departing from Portland which include Bailey Island and Mackerel Cove or Eagle Island. The tour has a 2-hour layover on Bailey Island for lunch at Cook’s Lobster & Ale House
You can also arrive by sea on a sailing charter, lobster tour, or even charter your own private tour.
Here are a few options you might consider to arrive at Bailey Island by sea:
- Tevake Sailing Charters
- Casco Bay Sites-N-Lights
- West Wind Lobster Tours
What to See and Do On Bailey Island Maine
As you can imagine, the pace is slower, here on Bailey Island. It’s an ideal destination for someone who loves to meander about, taking in stunning ocean views, eating the freshest seafood, and enjoying incredible photo opportunities.
My recommendation is to just take your time to casually explore this quaint little island on your own.
But if you prefer a more solid plan, there are a number of attractions you might put on your itinerary.
In fact, let’s go ahead and design a treasure hunt for you, even though you are likely to stumble upon many of these attractions yourself.
Bailey Island Maine Treasure Hunt
Listed in random order
- Cook’s Lobster & Ale House
- Bailey Island Bridge
- Bailey Island Beach
- “BIGS” – Bailey Island General Store
- Casco Bay
- Mackerel Cove (one of the most photographed places in Maine)
- Giants Stairway Trail
- Betty’s Seaside Creations
- Abner Point
- Giant Stairs Grille
- Bailey Island Lobster Co.
- Glen’s Lobsters
- Johnson Field Preserve at Mackeral Cove
- MacIntosh Lot Preserve
- Garrison Cove
- Harpswell Honey
- Harpswell Heritage Land Trust (lots of trails)
- Cedar Beach
- Morse’s Cribstone Grill
- Land’s End Gift Shop
One of my favorite scenic stops is Land’s End.
To get there, follow along Route 24 until it literally ends. You’ll know you’re getting close when you see a sign that warns “Road Ends 500 feet.”
Related Article: Find out what to pack for a Fall Trip to New England here.
And if you have a bit of time, definitely stop by Portland on your way to Bailey Island. While you’re here, you can take part in an amazing, 2.5-hour historical tour of the area. Tickets start at $40 per person and include expert commentary on over two-hundred years of history from a local guide.
You’ll start on Commercial Street and take a leisurely stroll through the town’s many cobblestone lanes as you explore the Old Port and the downtown waterfront area.
Along the way, you’ll admire the town’s famous lobster statue, see the former residence of Henry Wadsworth-Longfellow, visit the Eastern cemetery, stop by the Abyssinian Church, and end the day with a complimentary sweet treat from a local food vendor.
What is Land’s End in Harpswell ME?
Land’s End is a scenic destination at the southernmost tip of Bailey Island.
At Land’s End, you’ll find mesmerizing views of the Atlantic Ocean, Turnip Island, Jaquish Island, and a myriad of other small outcroppings. (Fun Fact: About 200 islands of Harpswell are reachable only by boat.)
You’ll also find the “Maine Lobsterman” sculpture as well as narrow walking paths along the shale.
The view is especially breathtaking from the deck of the Land’s End Gift Shop–not to be confused with the mail-order clothing catalog.
Where to Park at Land’s End
You’ll find two free parking lots located next to and across from Lands’ End Gift Shop.
Plus, it’s worth noting that portable restrooms are located in the first parking lot next to the gift shop.
Exploring Land’s End
While visiting Land’s End, you might choose to:
- Relax on the small, sea-glass strewn Bailey Island Beach
- Watch the boats cruise Casco Bay
- Admire the iconic ‘Maine Lobsterman’, a bronze statue originally created for the 1939 World’s Fair
- Walk along the rocky trail which ends at the Giant’s Stairway
- Cool off and shop the gift store for unique Maine-made souvenirs
At Land’s End, follow the path that meanders along the coastline to enjoy the stunning views of Casco Bay. You may even catch a glimpse of seals, seabirds, and other sea life.
Here’s a great aerial video of the area to give you a taste of the natural beauty you can expect while visiting Land’s End:
If you follow along the coastal path, I’m told you will arrive at what’s known locally as “The Giants Steps,” a natural rock formation that looks like stairs leading down to the sea. (Tip: Watch out for poison ivy.)
On the trail, you’ll encounter a small rocky beach called Pinnacle Rock is where you’ll want to keep your eyes out for sea glass. Watch for the waves crashing in “Thunder Hole,” too.
A Must-See: The Gift Shop
Land’s End has a large gift shop with home-made fudge, light snacks, water, and, more importantly, a large selection of Maine-made souvenirs.
Two floors are filled with artisan goods, trinkets, t-shirts, and more, crafted by nearly 100 Maine artisans.
Trust me, you’ll want to spend some time here to take it all in. This is souvenir heaven.
Land’s End Gift Shop has been owned and run by the Hutchins family since 1959. It was originally a small snack bar and store opened by Ed Hutchin’s grandparents in the 1930s. (The building was fully remodeled in 1978 after a damaging January storm.)
Today, Land’s End is run by Ruby and Ed’s son, Howard Hutchins, along with his wife Karen.
In addition, the shop provides plenty of benches on the wraparound deck (alive with whirligigs) overlooking the waterfront. It’s a perfect resting point if you want to sit comfortably and take in the view of Casco Bay.
That’s what I did. I loved catching some rays here, sipping a ginger beer, and taking it all in.
Best Time of Year to Visit Land’s End Gift Shop
Despite Harpswell’s reputation as a seasonal community, Land’s End Gift Shop is open seven days a week from April through October, weekends in December, school vacation week in February, and weekends in March.
New England winters can be bitter cold, especially on the coast. A visit to Land’s End in the spring, summer, or fall might be the better timing.
Land’s End Beach
Adjacent to Land’s End Gift Store, you’ll find the diminutive Land’s End Beach. Just a few steps down from the small parking lot, it’s known for sea glass and it’s lovely views of the ocean.
You may also enjoy swimming in the soft sandy bottom beach–but remember, the ocean water at Maine beaches can be cold!
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Land’s End is at the southern tip of Bailey Island, one of three small islands in Harpswell that are connected to the mainland by bridge. (The other ~200 islands of Harpswell are only reachable by boat.🚤) . At Land’s End, you’ll find a path that meanders along the coastline, offering stunning views of Casco Bay. There’s also a small rocky beach called Pinnacle Rock. (Keep your eyes out for sea glass!) #baileyisland #harpswell #itsamainething #visitmaine #enjoytravellife #newengland #visitnewengland #falltravel #autumnfoliage #fallfoliage #cascobay #giantsstairs #giantssteps #bayview #maine_igers #mainething #vacationstyle #mainevacation #newengland_igers #newenglandlife #travelblogger #travelwriters #travelpicture #travelpictures #traveltheworldwithme #ísland #maineislands #ilovemaine #roadtripusa .
This beach is said to have a lot of sea glass at low tide so for the best chance to find sea glass be sure to check the tide charts and plan to arrive an hour or two before low tide.
Where to Stay on Bailey Island
When we visited this area, we were staying in the nearby town of Brunswick. But, I could have easily been persuaded to overnight on Bailey Island.
In addition to several cottages on the island, you might consider one of these excellent lodging choices.
Bailey Island Motel
Just over the Cribstone Bridge and situated on the water’s edge, Bailey Island Motel is a great family-friendly option within walking distance to popular attractions. You’ll find decks overlooking the water, evening campfires, and complimentary use of their kayaks, too.
Waterside rooms at this modest but comfortable motel are well-priced at $130 per night and include complimentary breakfast (coffee, tea, freshly baked muffins), cable TV, free WIFI, ocean views, minifridges, and access to a private dock.
Log Cabin Island Inn
You’ll find breathtaking sunset views of the bay and a firsthand look at lobster boats at Log Cabin Island Inn. Plus, each room is uniquely styled; some suites are quite spacious with full kitchens and a jacuzzi. All are well-appointed. Enjoy a full complimentary breakfast, and you may opt for a delicious dinner with your stay, as well.
The Driftwood Inn
The Driftwood Inn is the oldest Inn on Bailey Island and has been in continuous operation for over 100 years. It offers pristine, private cabins for rent on their three-acre oceanfront location overlooking beautiful Casco Bay. Hosting includes housekeeping services and the use of their saltwater swimming pool. Or, rent “The Mansion,” which literally sleeps a full house, up to 16 guests.
Capt. Lawrence E. Johnson House
Perhaps one of the most luxurious accommodations on Bailey Island is the Capt. Lawrence E. Johnson House. It comfortably hosts up to ten guests, making it perfect for family holidays and events. Each room, which includes ensuite bathrooms, luxury linens, and cozy sitting areas, offers a different view of the inlets and sounds surrounding the island.
The wrap-around deck provides outdoor dining with a gas grill and a three-burner outside range. Plus, you’ll want to check out the rooftop deck complete with a wet bar. You might even be tempted to rent this property for a month at a time.
Bailey Island makes a memorable day trip if you happen to be within driving distance of Harpswell, Maine. And if you’re further away, even better; plan to stay over on the island to fully experience the relaxed vibe, coastal beauty, and “Down East” hospitality you’re sure to encounter.
Have you visited someplace in Maine or elsewhere as charming as Bailey Island? Please share it with me in the comments below.
This article may contain affiliate links. As always, all opinions expressed are my own. For more information, please see the following Disclosure.
In alphabetical order
Bailey Island Lobster Co.
51 Abner Point Road
Bailey Island, ME 04003
Phone: (207) 833-6099
W. Shore Road
Bailey Island, ME 04003
Phone: +1 (207) 833-5858
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