Forget Boston, Retire To Massachusetts' Underrated Lakeside City With Charming New England Sights Instead

From housing to medical care, retirement is getting more and more expensive. According to the Pew Research Center, the average age of retirement has been steadily rising over the last few decades, with about 19% of adults ages 65 and older being employed today, compared to just 11% in 1987. That's why it's important to settle down in a place that has all the necessities — access to medical care, a vibrant community, and (ideally) a bit of natural beauty — without breaking the bank. Especially in New England, one of the country's most expensive regions, it can be challenging to check off every item on the list. That's where Pittsfield, Massachusetts, has you covered.

Over 20% of the population in Pittsfield is over the age of 65, and the town ranks among the area's comfiest retirement destinations that don't break the bank. Although the cost of living is still slightly higher than the national average by about 10%, it's more than 25% lower than the state average. In other words, this city in the Berkshires is a comparatively affordable alternative to most towns in Massachusetts, a state that's home to four of New England's five wealthiest suburbs.

Pittsfield is about 140 miles west of Boston, and, in fact, far closer to Albany, New York. Here, you'll find everything you need for a healthy retirement: charming New England sights beside Lake Onota, hospitals like Berkshire Medical Center, a quaint downtown, and even a historic Shaker Village that dates back to the late 18th century. 

Pittsfield is considered highly walkable. The majority of shops, restaurants, and entertainment options are concentrated along North Street and South Street, which are separated by Park Square. There's also a fixed-route bus available for seniors.

You'll find a wide range of eateries downtown, from classic American diners to steakhouses, sushi, and family-owned Brazilian restaurants. Soda Chef, for instance, serves up breakfast with a healthy dose of nostalgia. "It's like going back in time, prices included," reads one review on Tripadvisor. In other words, it's ideal if you're hoping to relive memories of the past, like 1970s-era Hamburg and reasonably-priced plates. Down the block, Sibaritas is an upscale alternative for special occasions. It offers dishes like lobster ravioli, half-roasted duck, and squid-ink linguini.

The streets here are about as classically New England as it gets: brick-lined with the occasional church steeple poking through the trees. In residential areas, you'll find old-school Colonials and Cape Cods, and the average home value hovers slightly above $300,000, several hundred thousand less than Boston's average. Pittsfield also has plenty of live entertainment options, like The Colonial Theatre on South Street, where you can buy tickets for musicals and touring acts, with discounts for Berkshire residents. There are also senior discounts at The Boyd-Quinson Theater, part of the nearby Barrington Stage Company. Not too far from downtown, you can also swing by the Berkshire County Historic Society, located in the former home of "Moby Dick" author Herman Melville. 

The city of Pittsfield borders Lake Onota and Pontoosuc Lake, where locals can go fishing, boating, or swimming. On Wednesday nights during the summertime, Burbank Park beside Onota hosts a free music series called Live on the Lake. Attendees set up blankets, beach umbrellas, and chairs to listen to bands play. "I love this place," reads one Tripadvisor review of the lake. This reviewer goes on to praise how clear the water is and add, "I travel past other lakes just to swim and fish at this one." In Boston, beside the harbor, or in beachfront destinations like Cape Cod, you might find yourself competing for resources. This won't be the case in Pittsfield, where the waterfront is described as "chill" and "good for meditation" by reviewers on Google.

Pittsfield is also known for its wheelchair and walker-friendly trails, like the Tranquility Trail in Pittsfield State Forest on the opposite side of the lake. Adults 62 and older can apply for a parking pass and enjoy a day exploring all the state forest has to offer, from canoeing and fishing to horseback riding and even off-roading.

Additionally, the city is home to the Ralph J. Froio Senior Center, a four-story complex that hosts fitness and exercise classes as well as ceramics, woodworking, and poetry courses. Google reviews for the space are overwhelmingly positive, with guests highlighting the game room and group trips around other towns in The Berkshires, which has long been one of New England's most iconic fall destinations with vibrant, leafy views and historic charm.