8 of the Friendliest Towns To Retire In Maine
There are plenty of reasons to love the rugged East Coast of the United States, and Maine sits at the top of the list. Boothbay Harbor is one standout, with the Coastal Maine Botanical Gardens and Windjammer Days bringing neighbors and visitors together. Camden is another, with its beautiful harborfront and Main Street, with easy access to Camden Hills State Park. So if you’re a retiree who craves fresh air and four seasons, you’ll be in good company, as Maine consistently ranks among the states with the oldest population in the US, with a median age of 45.
Kennebunk
Kennebunk is a classic seaside town with clean, sandy beaches, a walkable downtown, and a large senior population whose median age is about 55. This is an attractive spot for retirees to enjoy outdoor activities like fishing, boating, beachcombing, and dog walking along Kennebunk’s dog-friendly beaches like Gooch’s, Middle, and Mother’s. A little quieter than Kennebunkport, made famous by US Presidents George H.W. Bush and George W. Bush, Kennebunk is ideal for retirees who like the idea of living in a beach town without the annual influx of summer tourists.
Get to know the neighborhood with a free walking tour that winds its way past 25 historical panels installed around town called Museum in the Streets. The friendly, close-knit community also hosts numerous events, including the popular Kennebunk Farmers’ Market and the Kennebunk Artisans Marketplace, both held every Saturday, from May through October and November, rain or shine.
Hallowell
Only three miles from the state capital of Maine, Augusta, the riverside town of Hallowell is a good choice for retirees who enjoy spending time in both urban spaces and nature. The town sits on the Kennebec River, making it easy to access the water to launch a kayak or fish for bass, salmon, and trout from the shore. For avid cycling enthusiasts, the 6.5-mile Kennebec River Rail Trail connects the town to Gardiner, Farmingdale, and Augusta, with two trailheads in downtown Hallowell. The trail is part of the East Coast Greenway, a network of trails that, once complete, will run from Key West, Florida, to Calais, Maine.
Art and culture lovers can explore the 1938 Gaslight Theater, the oldest continuously operating community theater in Maine, and join in on the biannual Hallowell Artwalks, when downtown hosts all-day displays by local artists. For live music, 38 microbrews and domestic beers on tap, and pub-style eats like nachos, pizza, and burgers, check out the Quarry Tap Room, which calls itself “Hallowell’s Deepest Watering Hole.” The median age of residents in Hallowell is 50.
Boothbay Harbor
Boothbay Harbor is about an hour north of Maine’s largest city, Portland, making trips to the big city an easy drive for young-at-heart retirees who want to enjoy Portland’s award-winning eateries and happening nightlife. Back in town, where the median age of residents is 63, enjoy all the benefits of living next to the largest public garden in New England, the 323-acre Coastal Maine Botanical Garden, by joining one of two free daily tours when the garden opens May 1. Choose from an hour-long “Highlights Tour,” or head out on a fun 90-minute “Hike the Trolls” walk to find 5 trolls hidden in the woods.
Discover the town’s most-recognizable landmarks, the iconic Boothbay Harbor Footbridge, which connects the busy downtown to the east side of the harbor, where you’ll find historic homes and inns for visiting children and grandkids. Built in 1901, the footbridge was widened for accessibility in 2023 and enhanced with LED lighting. Be sure to join the town’s 64th annual Windjammer Days, a weeklong festival of sailing ships that includes a decorated boat parade, a lobster-eating contest, crab cake cookoffs, concerts at the 1894 historic Opera House, and much more.
Belfast
Retired theater lovers will find what they are looking for in Belfast, a spirited town at the mouth of the Passagassawakeag River (“Passy,” to locals), where it empties into Penobscot Bay. Known for its vibrant arts scene and plenty of local festivals, one-of-a-kind shops, and community engagement, retirees can enjoy strolling along the Belfast Harbor Walk with residents who have a median age of 60. For a longer walk, take the gravelly 2.3-mile Belfast Rail Trail that passes through woods as it follows the river. You’ll find the trailhead at the City Point Central Railroad Museum, where you can take a pit stop to learn about the history of the railroad in Belfast and see vintage locomotives and carriages.
At the heart of Belfast’s busy theater scene is the Belfast Maskers, a community theater group that produces plays and musicals, giving locals of all ages and abilities a chance to act, volunteer at the front of house, or join a committee. The United Farmers Market of Maine is a community hub in Belfast where farmers, artisans, and foodies get together indoors every Saturday.
Camden
Camden may well be the quintessential Maine coastal town with a pretty harborfront, unique shops and restaurants along its Main Street, and the Camden Village Green, a historic park surrounding a memorial flagpole honoring World War II soldiers, and the perfect place to relax after a day of shopping. Not-to-be-missed Camden Hills State Park is a huge 5,700-acre park where active retirees can enjoy 30 miles of hiking trails, and an 800-foot climb to the summit of Mount Battie for spectacular views of Camden Harbor, the islands of Penobscot Bay, and, on a clear day, all the way to Cadillac Mountain in Acadia National Park.
Considered a top sailing bay, retired sailors can charter a boat from the Camden Harbor, choosing from everything from a one-hour powerboat excursion to a 3-day cruise aboard a Windjammer. Against the backdrop of the harbor, the small town rolls out the red carpet twice a year (July and October) for the long-running Camden Harbor Arts & Crafts Show, with exhibitor booths filling up Camden Harbor Park and surrounding the Camden Amphitheater, both spaces listed on the National Register of Historic Places. The median age of residents in Camden is 52.
Stonington
Stonington is a town on the southern tip of Deer Isle, accessible by the Deer Isle Bridge, a historic suspension bridge that connects the mainland to the island over the Eggemoggin Reach. Less touristy than many Maine towns, Stonington has a real working waterfront, complete with fishing boats hauling in lobster traps, so grab a patio table at Stonecutters Kitchen and enjoy the view of Stonington Harbor over lobster rolls and cold drinks.
Island living is definitely suitable for retirees who like spending time on the water with neighbors who have a median age of 58. The Island Community Center is the town’s go-to hub for events like its annual “Christmas in July Craft Fair,” as well as other celebrations at Easter, Halloween, and Thanksgiving.
Known as the Stonington Archipelago, Deer Isle sits among about 70 islands, making it a sea kayaker’s paradise. Paddle around the coves and pretty islands, or book a guided outing with Osprey’s Echo Sea Kayaking, which offers everything from a 2-hour adventure eco tour to a full-day excursion to learn about the area’s history, culture, and coastal wildlife such as seals, porpoises, osprey, and more. Watch the sunset from Sand Beach with a hot brew-of-the-day from local coffee roasters 44 North Coffee.
Eastport
Join the majority of residents over 60 years old who live in Eastport, a tiny seaside community that sits across Passamaquoddy Bay from New Brunswick and the easternmost city in the US. Part community hub, part activity center, the Eastport Arts Center is a good way to connect with like-minded people. The center hosts author events, film screenings of blockbusters and indie classics, a popular concert series, special events, and more, entirely run by volunteers.
For arts and culture enthusiasts, the unique Tides Institute & Museum of Art comprises about a dozen historic cultural sites along the eastern coast of Maine near Canada, perfect for immersing yourself in the area’s art, history, and heritage. The sites include two early 19th-century churches, a brick Masonic Hall built in 1887, and an 1889 cast-iron water fountain. Explore more of Eastport’s history with a visit to S.L. Wadsworth & Son, the oldest ship chandlery and Maine’s oldest retail store. Founded in 1818, the business is currently run by the 6th generation of the same family and sells a wide assortment of hardware products.
Wiscasset
Just an hour from Portland, the pretty village of Wiscasset is an easy choice for retirees ready for whatever life has in store next. With a median age of around 48, the town attracts residents who appreciate art, architecture, and history, making it a gem for culture hounds. Full of art galleries, historic homes, and museums, the area is home to a standout: the 1811 Lincoln County Museum and Old Jail, one of three properties managed and maintained by the Lincoln County Historical Association (LCHA). The LCHA has several volunteer opportunities, including publicity, fundraising for their annual “Preservation Party,” and training to be a docent.
Wiscasset is a stop on any foodie’s tour of the East Coast, especially lobster fans who make the drive without hesitation to enjoy the world-famous lobster rolls at Red’s Eats. Still with food, Wiscasset is home to the Maine Tasting Center, a unique organization that supports Maine’s small food and beverage producers, like fishermen, farmers, and makers. Drop in and take a cooking class in the Learning Center, enjoy a local brew in the Tasting Room, or learn about Maine’s food and drink industry in the Discovery Center.
Older, Wiser, and Happier in Maine
Whether you’re in search of coastal charm, access to nature, affordability, or a ready-made community of neighbors your own age, there is no shortage of welcoming small towns in Maine to call home. With walkable downtowns, farmers’ markets and festivals, access to nature, and plenty of opportunities to join a local community group, these eight friendly towns in Maine are great for staying active, embracing the second chapter of life, and finding like-minded people.
