Set apart from the bustle of the mainland, islands have always held a special allure, and Maine is blessed with an abundance of these idyllic havens. Getting to an offshore outpost, however, can be a little daunting. Happily, you don’t have to board a boat or a plane to visit these 5 endearing isles that beckon from just beyond the tips of scenic coastal peninsulas. Just drive across a bridge or a causeway, and you’re there.
1. Bailey Island
The outermost of a chain of 3 bridge-linked islands that dangle from the coast between Brunswick and Bath, Bailey Island has been a beloved summer hideaway for at least a century. Part of the town of Harpswell, the 2-mile-long island is known for its scenic coves, rocky shoreline, and charming cottages and bungalows. The road to the island snakes onto a 1,150-foot-long bridge that’s barely wide enough for 2 cars. Its unusual “crib stone” construction rests on 10,000 tons of 12-foot-long granite slabs stacked in an open grid with no mortar, allowing the tide to flow through.
Before crossing the bridge, satisfy your sweet tooth and see treats being made at Island Candy Company. Once sated, seek out the Giant’s Stairs Trail, an easy, seaside path leading to a staircase-like rift in the sedimentary rock. For some sightseeing under sail, step aboard the schooner Alert, which docks beside the ever-popular Cook’s Lobster & Ale House.
Down at Land’s End, at the island’s southern tip, you’ll find a 7-foot-tall bronze statue of a lobsterman overlooking the sea. Beside it, a barn-size gift store brims with Maine keepsakes. Before heading back up island, stop at Mackerel Cove, a postcard-perfect fishing harbor with a pocket beach that’s great for a picnic.
2. Georgetown Island
Lying to seaward just east of Bath, Georgetown entices with an unbeatable combo of award-winning lobster rolls and one of the state’s most spectacular beaches. Follow Route 127 across a little bridge over Back River and onto Georgetown. Continue until you see a large American flag painted on a rock on your right. Turn there for Reid State Park, whose unspoiled, mile-long sand beach invites a leisurely walk and perhaps a brisk dip. Clamber up rocky Griffith’s Head for an ocean panorama speckled with islands, including storied Seguin Island.
Return to Route 127 and continue to the western edge of Georgetown and the exquisite harbor of Five Islands (there are at least 5 islands just offshore). You might arrive to see lobstermen sliding crates of freshly hauled lobsters across the pier. At a big waterside shack, Five Islands Lobster Company serves up generously stuffed lobster rolls as well as other seafood fresh from the boats tied alongside. If you’d like to linger longer on Georgetown, consider renting a houseboat at Derecktor Robinhood Marine Center in nearby Riggs Cove.
3. Southport Island
When you’re ready to escape the tourist thrum of Boothbay Harbor, hop next door to Southport Island. You may have to wait a few minutes for the 83-year-old swing bridge to open for boats passing through, but soon you’ll be driving—or biking—along the tree-lined road that rings the arrowhead-shaped island. Halfway down the western side, detour to Hendricks Head Beach for a walk on the sand, a scramble on the rocks, and views of the eponymous lighthouse (not open to public).
Revered environmental author Rachel Carson loved this spot and built a cottage nearby in the 1950s. She often visited the Newagen Seaside Inn, a traditional summer destination sprawled at the island’s southernmost point, and her ashes were scattered from the shore here (ask at the inn for directions to a plaque marking the spot).
Look across the harbor to Cape Island and the red farmhouse where Margaret Hamilton—a.k.a. The Wizard of Oz’s Wicked Witch of the West—spent many summers. Before driving back across the bridge, stop right beside it at Robinson’s Wharf to munch a lobster roll while watching lobster boats offload their catch.
4. Deer Isle
Turn off US 1 east of Bucksport, follow winding byways for some 30 miles, cross the Deer Isle Bridge, and you’ll finally arrive on Deer Isle. Stop in the charming Deer Isle Village to peruse several art galleries or grab a fresh-roasted coffee at 44 North Coffee. Then continue to Nervous Nellie’s Jams and Jellies, on the island’s eastern side, to purchase delicious jams and explore Nellieville, a village of mini buildings and a forest inhabited by quirky, life-size characters sculpted from found objects.
Deer Isle enjoys a proud heritage of quarrying: Local granite went into Rockefeller Center and other major landmarks. The island has a number of hiking trails, including one that leads to an abandoned quarry.
Today, lobstering is the primary industry, with several hundred fishermen hauling in Maine’s largest annual landings out of Stonington. Paralleling the working waterfront, Main Street is lined with shops, galleries, and eateries. Join locals for breakfast or lunch at Harbor Café or coffee at 44 North’s second location. For dinner, walk to Fin and Fern, head a few miles out of town to Aragosta at Goose Cove, or return to Deer Isle Village and the Whale’s Rib Tavern. In the evening, check out what’s on at the Stonington Opera House, whose green facade has overlooked the fish pier for 110 years.
Tucked away on Maine’s downeast edge, Eastport perches just across Passamaquoddy Bay from New Brunswick, Canada. From US 1 near Perry, follow the road onto a causeway to Moose Island, home to petite Eastport—the easternmost city in the U.S. Stop at the massive breakwater in the middle of downtown for sweeping views across the broad, deep harbor to clusters of Canadian islands, including Campobello. In the warmer months, keep an eye peeled for whales, which often swim near shore. For a closer look, sign up for a whale-watching trip or scenic boat ride.
In the early 20th century, Eastport boasted a booming sardine industry. All that remains is an antique stone-ground mustard mill, still churning out the yellow condiment that went into countless sardine tins. Stroll from the breakwater through the historic Water Street shopping district to Raye’s Mustard Pantry Store to pick up a jar of the original condiment or one of numerous newer flavors. Be sure to check out Water Street’s other appealing shops and galleries, plus several down-home eateries and a craft brewery (be sure to designate a driver if you plan to drink alcohol).
Nearby, the Tides Institute & Museum of Art illuminates Eastport’s rich history through a collection of historical and contemporary pieces. On the western side of Moose Island, Shackford Head State Park offers excellent hikes through the woods to dramatic seaside headlands.
Mimi Bigelow Steadman writes about New England regularly for AAA’s publications.
Travel offers & deals
Hot travel deals
Get the latest offers from AAA Travel’s preferred partners.
Travel with AAA
See how we can help you plan, book, and save on your next vacation.
Save big with AAA discounts on tickets to your next adventure.
Travel with confidence
Purchase travel insurance with Allianz Global Assistance.