Bailey Island Maine: How to Plan a Day Trip to Breathtaking “Lands End”

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.

A view of the Atlantic Ocean and islands as seen from Bailey Island Maine

CONTENTS: In this article, you will learn everything you need to know about planning a trip to Bailey Island Maine, including:

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

Map pointing out 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

Cribstone Bridge in Harpswell Maine, crossing over to Bailey Island Maine

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

Boats on the water at the Cribstone Bridge in Harpswell 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?

Lands End in Harpswell (Bailey Island Maine)

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 .

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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.

Click to see Bailey Island Motel Rates & Availability

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.

Click to see Log Cabin Island Rates & Availability

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.

Click to See The Driftwood Inn Rates & Availability

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.

Click to see Capt. Lawrence E. Johnson House Rates & Availability

Final Thoughts

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.

Jackie Gately of Enjoy Travel Life at Bailey Island Maine

Have you visited someplace in Maine or elsewhere as charming as Bailey Island? Please share it with me in the comments below.

How to Plan a Trip to Scenic "Land's End" on Bailey Island Maine, from Enjoy Travel Life.
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In alphabetical order

Bailey Island General Store (“BIGS”)
2124 Harpswell Islands Road
Bailey Island, ME 04003
Phone:  +1 (207) 833-2400
More Info

Bailey Island Lobster Co.
51 Abner Point Road
Bailey Island, ME 04003
Phone: (207) 833-6099

Bailey Island Motel
1951 Harpswell Islands Road
Bailey Island, Maine 04003
+1 (207) 833-2886
Email: [email protected]
Check Rates & Availability

Betty’s Seaside Creations
47 Washington Avenue
Bailey Island, ME 04003
Phone:  +1 (207) 833-6645
More Info

Capt. Lawrence E. Johnson House
1965 Harpswell Islands Rd
Bailey Island, ME 04003-2573
Phone: +1 (207) 541-9187
Email: [email protected]
Check Rates & Availability

Casco Bay Lines
P.O. Box 4656
Portland, ME
Phone: +1 (207) 774-7871
Email: [email protected]

Casco Bay Sites-N-Lights
1945 Harpswell Island Road
Bailey Island, Me. 04003
Phone: Cell – +1 (207) 837-1788 | Home – +1 (207) 406-2124
email: [email protected]

Cook’s Lobster & Ale House
68 Garrison Cove Road
Bailey Island, Maine 04003
Phone: +1 (207) 833-2818

Driftwood Inn
1958 Harpswell Islands Road
Bailey Island, ME 04003, USA
Phone: +1 (207) 833-5461
Email: [email protected] | [email protected]
Check Rates & Availability

Giant Stairs Seafood Grille
2118 Harpswell Islands Road
Bailey Island, Maine 04003
Phone: +1 (207) 833-5000
More Info

Glen’s Lobsters
Abner Point Rd
Bailey Island, Maine 04003
Phone: +1 (207) 833-6138
More Info

Harpswell Honey
W. Shore Road
Bailey Island, ME 04003
Phone: +1 (207) 833-5858

Lands End Gift Shop
2391 Harpswell Islands Road
Bailey Island, ME
Phone: +1 (207) 833-2313
Email: [email protected]

Log Cabin Island Inn
5 Log Cabin Road
Bailey Island, ME 04003
Phone: +1 (207) 833-5546
Check Rates & Availablity

Morse’s Cribstone Grill
1945 Harpswell Islands Road
Bailey Island, ME 04003
Phone:  +1 (207) 833-7775

Tevake Sailing Charters
Sea Escape Charters 
3 Sea Escape Lane
Bailey Island, ME 04003
Phone: +1 (207) 841-9125 (cell) | +1 (207) 833-5531

West Wind Lobster Tours
1945 Harpswell Islands Road
Bailey Island, Maine 04003
Phone: +1 (207) 939-5481

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Jackie Gately

Jackie Gately is a seasoned travel writer, photographer, and marketing consultant who is passionate about travel. She loves casual-luxury experiences, coastal getaways, cultural attractions, and local, wholesome food and wine pairings. A perfect day ends with her toes in the sand or by chasing the sunset with her camera--ideally both.

22 thoughts on “Bailey Island Maine: How to Plan a Day Trip to Breathtaking “Lands End”

  • July 28, 2020 at 11:58 pm

    It’s so wonderful to read that three generations took a road trip together to Maine. I loved your video. I felt i was there exploring the region with you. I love exploring small and offbeat places. I would love to explore Bailey Island for its quaint charm.

    • July 29, 2020 at 4:03 pm

      It was such a treat to take a multi-generational trip. I’m so glad you enjoyed exploring Bailey island in this post and video. It certainly is quaint and charming!

  • July 28, 2020 at 8:16 am

    This is the first time I have heard of Bailey Is. Your guide is so comprehensive with all the smallest details. I’m just surprised by so many things to do in such a small place. Definitely, a good place to unwind when you need to.

    • July 29, 2020 at 4:06 pm

      Thanks for your kind words, Arv! It’s amazing the details that come to light when you thoroughly explore even a small place like Bailey Island, isn’t it? And, you are absolutely right–I think it’s one of the places to unwind.

  • July 27, 2020 at 8:54 pm

    1 pound of tobacco and 1 gallon of rum. That’s a pretty good cost history. 🙃 Lands End really looks like a place for a perfect staycation. I myself have loved such serene places away from the humdrum. I would also like to know more about the Cribstone bridge, as to what made it special from a civil engineering viewpoint. Loved reading! 🌸

    • July 27, 2020 at 9:14 pm

      Thanks, DoiBedouin! I’m glad you enjoyed this article. If you love serene places, you’ll love Bailey Island. Also, the Cribstone bridge as built relies only on gravity to hold it together–even with cars driving over it and the tides going through. 90 years later, still standing!

  • July 27, 2020 at 4:13 pm

    How charming. I love places like this, with a slower, more relaxed vibe. I can see that Bailey Island would be a great place to spend some time. I would really enjoy looking for sea glass and visiting the Land’s End Gift Shop. Your description of the whole place made me think of the Hallmark movies.

    • July 27, 2020 at 9:14 pm

      It would be the perfect place for a Hallmark movie!!

  • July 26, 2020 at 9:36 pm

    Bailey Island looks like a wonderful day trip, such lovely scenery. Anywhere with that many establishments with ‘lobster’ in the name has to be worth planning a long walk around followed by a seafood lunch 🙂 I’d even be tempted to stay there overnight.

    • July 27, 2020 at 9:48 am

      Haha, I feel the same way. Lobster served any way, is my favorite! You’ll find plenty in Maine. Even better if you can stay overnight.

  • July 26, 2020 at 7:47 am

    Bailey Island Maine sounds like a charming and laidback town. An ideal getaway to relax and rejuvenate, far from the rat race of the cities. I think just spending a few days here and absorbing in the atmosphere would be therapeutic. Land’s End looks to be enchanting with some spectacular views.

    • July 27, 2020 at 9:50 am

      You’ve got that exactly right! It’s completely therapeutic, and you’ll find lots of gorgeous views, especially at Land’s End.

  • July 26, 2020 at 12:36 am

    Thanks for Introducing me to a new place! That rugged beach looks so lovely and unique. I haven’t spent much time in New England but I’m definitely feeling more inspired now.

    • July 27, 2020 at 9:51 am

      You’re welcome! And I hope you have a chance to experience New England again soon, Mona. I feel so lucky to call it home.

  • July 24, 2020 at 7:35 pm

    I live in New England, but I have never heard of Bailey Island!! It looks so beautiful and quaint. Adding this to my things to see this fall bucket list!

    • July 25, 2020 at 11:29 am

      Wonderful to hear you are local! Bailey Island will make a great fall trip. Enjoy!

  • July 23, 2020 at 9:32 pm

    What a charming island! And I love that it’s so close to my “new” home, easy weekend trip for me. 🙂 Bridges somewhat terrify me, I don’t know if I could cross the Cribstone Bridge! I might need to head up to go Christmas shopping at the Land’s End gift shop.

    • July 24, 2020 at 11:23 am

      Yes, so close to where you are, Kendra! The Cribstone Bridge feels just as though you’re driving on the road–it’s paved and everything! Hopefully, it will not be so scary. (fingers crossed!)

  • July 23, 2020 at 2:27 am

    I would love to visit Maine at some point! This place in particular looks so pretty. All of the photos I see of Maine are stunning. I’m adding this one to my list!

    • July 24, 2020 at 11:23 am

      Great! Maine truly has such a unique beauty. Hope you get a chance to see for yourself, Krisa!

  • July 22, 2020 at 3:02 pm

    A roadtrip to Maine has been on my bucketlist forever. I will have to pencil in a visit to Bailey Island. I love exploring small towns and they are even better when on the ocean. From the way you have described it, it reminds me of one of the small fishing villages in Eastern Canada.

    • July 24, 2020 at 11:25 am

      I couldn’t agree more, Kelly. As you know, the Nova Scotia Maritimes are close to my heart. They and the islands in Maine are cousins! I hope you get down this way soon and have a chance to check out Bailey Island. You will really love it!

Comments are closed.