Forget Boston, Retire To New England's Vibrant Coastal Gem With Lighthouses, Islands, And Craft Brews

When you think of New England, you think of Boston: the history, the sports, the universities, the "Cheers" gang, the whole deal. Boston is one of America's genuinely great cities, but it's not the easiest place to retire. From housing and utilities to transportation and taxes, it can get expensive. The weather's no joke, either: Boston averages about 49 inches of snow a year, so you'll be spending plenty of time shoveling or indoors. Still, maybe you want to retire in New England. Fortunately, other cities in the region may be better suited to retirement than Boston. One such city is Portland, Maine.

Maine's largest city is a coastal gem that offers plenty of what people love about New England without Boston's big-city scale. In fact, Kiplinger named Portland one of the best places to retire in New England, based on factors such as cost of living, income, health care accessibility, recreation, and well-being. Portland is a charming little city right on Casco Bay, packed with scenic coastal splendor, while its downtown has many of the amenities and conveniences retirees might want in a modern city, but with a more laid-back atmosphere. That doesn't mean Portland is cheap. Housing costs can be high for a city its size, and Maine winters remain a consideration, but retirees also have access to major medical care and a range of senior-focused programs and recreation.

For instance, the city runs a voluntary Age-Friendly program that encourages local businesses to become more accessible and accommodating to older customers. It also offers recreation programs specifically for residents 62 and up, including shopping trips, outings to local attractions, and a popular "Mystery Lunch" excursion. Additionally, the city's long-running Inclusion and Adapted Services initiative offers recreational opportunities for people with disabilities. And if that's not enough for you, Portland's shoreline is full of both natural and human-made beauty, and the city boasts one of the country's best craft beer scenes.

Southern Maine's stretch of the fabled New England coast mixes sandy beaches with rocky coastline. From its perch on Casco Bay, Portland's craggy strip of shore offers easy access to several beautiful lighthouses and the small islands that dot the bay. Six scenic lighthouses sit within about 20 minutes of the city. Maine residents 65 and older get free day-use admission to state parks, and seniors can buy an annual vehicle pass for $45, making a trip to Two Lights State Park a bargain.

The park is in Cape Elizabeth, also home to Portland Head Light in Fort Williams Park. If it looks familiar, it's because the oldest lighthouse in Maine is also the most photographed lighthouse in America. Meanwhile, the former lightkeeper's house is now a museum, where you can learn all about lighthouses and Portland's nautical history. Other local lighthouses include the Spring Point Ledge Light on Portland Harbor, the only lighthouse in the area accessible by land; Portland Breakwater Light — better known as Bug Light – and the stark granite cylinder of the 72-foot Ram Island Ledge Light. The area is a haven for charming coastal lighthouses like these, with their striking architecture and old-fashioned warmth.

Those lighthouses look out on Casco Bay, home to islands that are small and even smaller. They're known as the Calendar Islands, supposedly because there's one for every day of the year. Some make great day trips, while others offer a quieter alternative to city life. Great Diamond Island is a short ferry ride from Portland, with waterfront views, the popular Diamond's Edge Restaurant & Marina, and the former Fort McKinley. At low tide, a sandbar connects it to the smaller, quieter Little Diamond Island. Peaks Island has a lengthy walking trail ideal for birding and views of the Bay, while Long Island is home to the Byers & Son Long Island Bakehouse, where you can grab oysters and lobster rolls.

Portland has been a top stop on Maine's beer trail for decades. Founded in 1983, Geary Brewing Company bills itself as New England's first post-Prohibition craft brewery and helped jumpstart what would become one of the most vibrant craft beer towns in the country. Today, there are over 20 craft breweries in the city, while Maine ranks among the states with the most breweries per capita.

Geary is still kicking, pumping out ales and porters as it has for four decades. But Portland's biggest and most famous brewery may be Allagash, which has been making Belgian-style beers since 1995. Allagash White is a modern American classic that helped popularize Belgian wheat beers in the U.S., and it remains a favorite today. Guests can drink White and other Allagash brews at the Portland taproom, which holds a 4.8-star rating on Tripadvisor and is also ranked as the top-rated activity in the city.

Other standouts include Bissell Brothers Brewing Company, which has been serving its signature award-winning IPA Substance Ale since the early 2010s. IPA-mad Belleflower Brewing was named one of the best breweries of 2023 by Hop Culture, while Oxbow Blending and Bottling specializes in farmhouse ales — fittingly, Oxbow's original brewery is located inside a converted barn. And although you won't see many senior or retiree specials at these taprooms, you can find happy hours offering discounts on beers from both Maine and abroad at bars and restaurants throughout Portland.