A view of the stacked granite slabs that make up the Bailey island Cribstone Bridge.



MY MAINE by Carter Smith

Bailey Island has always been a place where family and friends have gathered to reconnect.  Both with each other – and with the beauty and power of nature.  Bailey Island (and pretty much the whole state of Maine) is the perfect vacation spot for families who love the outdoors.  There are cliff walks along the dramatic shoreline. Magical woodland hikes where you can spot sunbathing seals and maybe even an elusive Maine Fairy House. There is delicious local seafood that’s as fresh as it gets. You can explore the coast by kayak or sailboat or paddle board.

Or you can sit back, relax, and do nothing at all, surrounded by friends and family.

Bailey Island offers families plenty to explore, and whatever you choose to do, you will surely leave with memories to last a lifetime. A guest at one of THE GILLS GROUP cottages summed it up when he wrote in the guestbook “Our family has never been so close, happy or active as we were during our weeks on Bailey Island.”

These are some of my favorite things to do when I have friends and family visiting Bailey Island…




No visit to Bailey Island would be complete without a trip to Land’s End. You’ll know you’ve arrived when the road comes to an abrupt dead end at the ocean. The beach is a popular spot to visit any time of year – and perfect for watching one of Maine’s incredible sunsets. You can see the Halfway Rock Lighthouse in the distance, and the small pebble beach is a great place for a quick dip in the ocean.

The bronze Lobsterman Statue on the point was created by Portland sculptor Victor Kahill in 1939 for the New York World’s Fair, and is “a memorial to all Maine fishermen who have devoted their lives to the sea.”




You’d be hard-pressed to find a wider selection of tourist trinkets than at Land’s End Gift Shop, which has been here since the thirties. The original shop was wiped out in the storm of 1971, but fear not, it’s been rebuilt, and you could probably spend hours inside and still not see everything. Whether it’s postcards or teeshirts or lobster lollipops, you’re sure to find something at this family run spot. If you’ve got a sweet tooth, make sure to check out their delicious house-made fudge.

Don’t miss the coin-operated viewing platform on the point, where you can get a closer look at nearby Jaquish Island or passing ships in the distance.






One of the best ways to spend the day on Bailey Island is to bring a picnic to the beach.  Grab some sandwiches at B.I.G.S (the Bailey Island General Store) and head to one of the island’s beautiful coves or beaches. Mackerel Cove is one of the most scenic working harbors in Maine, and it’s a perfect place to launch kayaks or paddle boards. A hedge of wild roses lines the pet-friendly beach, where you can hunt for sea glass as the lobstermen come and go from their moorings.



Cedar Beach is a more secluded spot, reached by a footpath at the end of Cedar Beach Road. At low tide, the beach becomes two crescents of sand – with a narrow spit of pebbles leading out to Cedar Island. As you scramble over the seaweed covered rocks, you’ll pass tide pools filled with all kinds of surprises. It’s great fun to explore – just make sure not to get stranded when the tide comes back in!  There are no pets allowed here, and visitors are asked to park before you reach Fathom Lane and walk the rest of the way in.





Harpswell (the township that Bailey Island is a part of) has over 216 miles of coastline – most of it perfect for exploring by kayak. There are plenty of trips for both beginner and experienced paddlers.

A great easy paddle is heading out from Garrison Cove toward the tip of Bailey Island. The water is calm and protected and you’ll get a great view of the cottages that line the shore. Don’t be surprised if a playful seal or sunfish swims alongside you. You could also paddle through the Cribstone Bridge and head to nearby Pond Island. Legend has it that a pirate named Lowe stashed his treasure there and haunts the island to this day.

For more of an adventure, head to National Historic Landmark EAGLE ISLAND to visit Admiral Robert Peary’s summer home. The historic “cottage” is a fascinating look at what life on a tiny Maine island was like a hundred years ago. The house is filled with nautical artifacts from Peary’s arctic explorations.  You could also check out the Peary MacMillan Arctic Museum at nearby Bowdoin College. A series of trails criss cross much of the island, which is also a bird sanctuary during nesting season.




H2OUTFITTERS  (housed in the red Salt Cod Cafe building just over the bridge on Orr’s) is the place to go for lessons, guided tours and rentals of both kayaks and paddleboards. Their sunset and full moon tours are spectacular, and the homemade pies and lobster rolls at Salt Cod are a perfect post paddling treat. There’s also a private pebble beach which makes a perfect launch site at THE RED HOUSE, one of The Gills Group Cottages.





Fairy House building is a tradition along the Maine coast. These fantastic little creations offer children and adults, a unique opportunity to explore and connect with nature. There is only one real rule to follow when building a Fairyhouse – use ONLY items that you find on the forest floor and be careful to not disturb anything living. Mosses and other native plants should be left untouched.

Instead, look for pine cones, feathers, and bits of sea glass. Driftwood and tiny bleached crab claws are everywhere, and often, it’s worth a trip to the rocks to collect your materials before you head back to the forest to build.

Some popular places to build (and discover) Fairy Houses are along Cliff Trail and on Senter Lane at THE GILLS. Cliff Trail is accessible from the parking lot at the Harpswell Town Office (263 Mountain Road), and winds along Strawberry Creek. It’s an easy hike, but there are sections with vertical drops of up to 90 feet, so keep a close eye on children and pets. The main loop is 2.3 miles and marked in white blazes. The shorter Cut-Off Trail is marked in yellow.

Wherever you build, know that you will be sparking pure joy in whoever visits your creation – as there are few things more magical than stumbling upon a fairy house in the forests of Maine.






Built in 1927 after a fiery local debate, the worlds only Cribstone Bridge stretches across Will’s Gut, connecting Bailey Island to Orr’s. At 1,150 feet, the bridge is built with huge granite slabs sourced from a quarry in Pownal, Maine. The open crib work construction allows for the ebb and flow of the tide and is a near perfect example of the simplest building technique – stacked stones.

It is recognized as a historic civil engineering landmark and is on the National Register of Historic Places. The best time to get a closer look is at low tide. On the Bailey Island side, a short couple steps lead down to the water from Morse’s Cribstone Grill, (a delicious spot for dinner and killer cocktails).  Or you could walk across the bridge to Orr’s and explore from there. There are few places more magical to watch a full moon rise over the ocean than from the Cribstone Bridge.






Exploring Casco Bay by sailboat is one of the best ways to take in the hundreds of islands along the coast. The Schooner Alert is a 70 foot Maine built, wooden tall-ship that offers two, four and six-hour cruises. Manned by Captain Bethany McNelly-Davis and her husband Perry, they do both sunset and full moon cruises, as well as private charters.

Stock up on wine and cheese at Black Sheep Wine Shop (or pack your own picnic) and enjoy a sail around the spectacular bay. The Alert leaves from the wharf at Cook’s Lobster House, and can also be hired out for private charters. They also offer sails on the smaller Tevake, a 31-foot ketch where you can help set the sails or just sit back and relax. Their Island Adventure cruise is an 8-hour expedition of sailing and hiking, and they can arrange to bring along a lobster bake.  You could even plan for an overnight stay on one of Maine’s wild uninhabited islands.






Devil’s Back trail is the perfect place to explore some of Harpswell’s quiet coves – no matter what time of year it is. In the winter, the trail is perfect for snowshoeing, and the rest of the year it’s a great hike for the whole family (including pets on leashes). Stop by the Island Candy Company to pick up some homemade treats on your way to the trailhead, which sits on Orr’s just before the bridge to Great Island. The moderate West Trail is 1.2 miles and slopes down through the pines over the rocky hump which the trail is named for.  Osprey and eagles are often seen fishing here, so be on the lookout for large stick nests high in the treetops. The East Trail winds along Gun Cove past Seal Ledge, where you can spot groups of seals sunning themselves on the rocks below at low tide.






This gentle winding trail is suitable for all ages and takes you along the rocky coast of Bailey Island’s eastern shore. Park at the All Saints By The Sea summer chapel and follow the paved road down toward the water. The well-maintained path (which is also pet-friendly) winds along the waters edge to The Giant Stairs – a rock formation beloved by locals and tourists alike. There are several smaller paths that branch off, leading down to dramatic stone beaches which are great for beachcombing or searching for pirates booty at low tide. The path then turns up through a thicket of wild rose and blueberry to the road.

You can either turn back the way you came or take a right and walk along Washington Avenue. You’ll pass by Betty’s Seaside Creations on the way. Her selection of handcrafted finds from local artists and crafters is top notch, and she has a great selection of tiny watercolor paintings by Margery Schuler – featuring many spots around the island.







With over 160 vendors, Cabot Mill Antiques in Brunswick is one of the best places along the coast to find unexpected treasures of all varieties. Housed in Fort Andross, a beautifully restored textile mill, there are over 1600 square feet crammed with everything from vintage paintings and porcelain to books, textiles, and furniture.  I’ve probably spent hundreds of hours roaming the aisles here, searching for that perfect piece for one of The Gills Group cottages.

On Saturdays and Sundays, there’s a  flea market that opens in the cavernous space next door, with vendors selling vintage vinyl, collectible ceramics, and pretty much anything and everything that you can imagine. The mill also houses the Brunswick Winter Market on Saturday mornings.

FRONTIER CAFE is on the other side of the mill with spectacular views of the Androscoggin River. They make delicious food (and drinks) focused on locally sourced ingredients. Frontier also houses a terrific arthouse cinema that screens an eclectic selection of indie and documentary films.



for more information about renting one of The Gills Group cottages email Dave@thegillsgroup.com





This is how I like lobster – sitting outside by the ocean surrounded by friends and family. The traditional way to eat lobster is everyone gets a single lobster then struggles to extract the meat before their cup of melted butter gets cold. I prefer to prepare lobster en masse, taking advantage of all the extra helping hands when I’m hosting guests. The idea is to steam as many lobsters as possible then sit in a circle and pick the meat out as a group – saving it to use later.  People are excited to roll up their sleeves and pitch in, and everyone ends up feeling this great sense of accomplishment at the end of it. I’ve done this with groups of six, and groups of twenty. It’s always a good time.  You end up with a massive amount of clean lobster meat that’s perfect for rolls, salads, stews, or pretty much anything else you can think of.

It also brings people together twice – once for the cooking/picking of the meat and again later at meal time.



I like to plan 2-3 lobsters per person because A. getting the meat out only gets easier once you know what you’re doing and B. you’ll end up with enough leftover clean lobster meat to keep everyone happy for days and C. you’re in Maine! Go for it.


An outdoor propane cooker fitted with a steamer basket is the way to go here, preferably one fitted with a strainer basket inside the giant pot (all of The Gills Group cottages are equipped with one). Fill the pot a little less than a quarter of the way full with heavily salted water. You want them to steam, not boil. Cover the pot and bring to a full rolling boil.  While the water heats up, lay out your lobsters and one by one and cut the rubber bands from their claws. Be careful!  When they’re fresh (like they are in Maine) they’re a far cry from the lazy glazed creatures you see in restaurant tanks. They will be feisty! At this point, some people will want to leave…and some may want to have lobster races.

Quickly and carefully place the lobsters head first into the pot and replace the lid.  You may have to hold it in place. They will thrash. They may make noise. It won’t last long if you’ve got a good boil and the lid stays tightly on. Return the water to a boil and let them steam for about 10-15 minutes until the shells are bright red. It may be a bit longer the more lobsters you have, but once they’re red, they’re ready.

Lift out the straining basket and let them sit until they’re good and cool.  Get a large bowl (or two) for the clean meat, and drain the water from the pot. Gather your crew outside on the deck/porch/lawn and arm them with lobster crackers. This is messy work best done outside within reach of a hose. You will be sticky and stinky when it’s all over but that’s part of the fun.


Once they are cool enough to handle, grasp the tail firmly in one hand and the body in the other. Twist apart, draining any liquid inside. Set the tail aside.

Twist off the claws where the knuckles meet the body. The claws, knuckles, and tail are where most of the meat is. You can suck the meat out of the little legs but it’s more novelty than nourishment. Use the large cooking pot to collect the shells as you go.

Pull off the tail flippers one by one.  When they are all gone you should be able to slip your thumb inside and carefully press out the tail meat. Collect all of the meat in a large bowl.

Next, use a cracker on the knuckles. Don’t forget about these – they can yield a surprising amount of meat.

Open the claw and break it with the cracker at its widest part. Crack it again toward the tip then use your finger or a small pick to push out the meat.




It gets soo much easier as you go, and in no time you have a mountain of lobster meat, and a huge pot of stinky messy shells. Carefully throw the shells back into the sea (not onto the rocks, and definitely not in the trash) then immediately wash the pot with soap and hot water. Believe me, you don’t want to wait a day to do this.  Put the lobster meat in a colander and rinse – cleaning off any nasty bits until you have a heaping mound of fresh clean lobster meat.  Chop the meat into bite-sized pieces – leaving the occasional small claw intact and getting rid of any bits of shell.

You’ve now got mounds of clean lobster meat and your options are endless.

If you want to go the more traditional route and order yours in a restaurant, both Cook’s Lobster House and Morse’s Cribstone Grill are good bets.

Here’s a MAP to all of the places listed in the BAILEY ISLAND FAMILY GUIDE.


The Gills Group is a collection of oceanfront rental cottages on Bailey Island, Maine. From a romantic honeymoon cottage for two built in 1920, to a family compound that sleeps 18, the Gills Group cottages can be combined to accommodate groups of all sizes. There are several spaces that are perfect for hosting artistic or corporate retreats, and a breathtaking sunset wedding venue with a 100 foot wharf and private beach.

Contact our property manager for more information.



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