Best Healthy Places to Retire: Longmeadow, Massachusetts

Less than an hour's drive from the majestic Berkshires of western Massachusetts, Longmeadow sits in a cozy 9-square-mile nook between Springfield, Mass., and Enfield, Conn. It may exude the feel of a quiet New England hamlet, but this affluent suburb is rich with activities—particularly for retirees, who account for roughly a fifth of the town's 16,000 residents.

The Connecticut River is rower Carole Shaw's workout space.

Location is a big part of Longmeadow's appeal. "The nice thing about living in this part of the world is that any direction you go, you're a half-hour away from real country," says 80-something Peggy Starr, who moved to Longmeadow with her husband more than 30 years ago. Not only are residents close to nature (and spectacular foliage in the fall), they're also just 20 miles from Bradley International Airport and a half-day's drive from Boston, New York, and the Adirondacks.

Another plus for outdoor enthusiasts: Nearly a third of Longmeadow is made up of parks and nature preserves, which include terrific bird-watching spots. "The Meadows" are a popular destination—specifically the 2-mile Pondside Road, where birders stroll with binoculars and field guides looking for migrating flocks. In the spring, lucky visitors might catch a glimpse of an osprey, a great egret, or even a bald eagle.

Garden spot. Longmeadow's maple-shaded streets are dotted with dozens of colonial-style homes built in the 1700s and 1800s, many of which surround the town green—the state's longest. Some houses are separated by "dingles," which are tree-lined ravines that often contain a stream. Gardening is practically a religion here. You'll find both community plots and yards overflowing with flowers, shrubs, and often vegetables. "Even small properties have a few cornstalks or pumpkins, and I don't know anyone who doesn't grow tomatoes," says Linda Abrams, curator of the town's historical society. Just about every weekend from May to September, Longmeadow's vintage baseball team is in action at Storrs Park or on the road. The game features 1860s-era uniforms, equipment, rules, and "gentlemanly play," says organizer Paul Sheehan. "The nuances in the rules and customs really show people how the game was once and still should be played."

On the town's western border, the Connecticut River is home base for the Pioneer Valley Riverfront Club, which offers rowing classes for youth and adults. A local yacht club hosts sailboat races on Sundays throughout the summer. Meanwhile, plenty of leisurely but low-key activities can be found at Longmeadow's adult center, which offers everything from tai chi classes to workshops on jewelry-making—and, of course, afternoon tea. Bottoms up.