The 5 Best Cities To Retire To In Massachusetts

Let’s be honest, Massachusetts is not a retirement destination.   Instead it’s one of the many, high tax, high cost of living northeastern states that represent places you live and retire to if you grew up there and/or have family there.   It comes in at number 40 on our best states to retire to list mostly because of the high cost of living and cold winters.    We’re not going to try and hide our bias for warmer southern states at all.  However, if you were forced to retire in MA, then here are 5 of the best cities to retire to in Massachusetts.


Best Cities To Retire To In Massachusetts - Retire To Springfield Ma

Home to the Naismith Memorial Basketball Hall of Fame, Springfield, MA is perfect for retirees that want a bustling mid-sized city but don’t want to live in one of the mega cities like Boston.  With its vibrant downtown, numerous cultural institutions, and first-rate health care providers, it’s no wonder that so many retirees have chosen Springfield and the Pioneer Valley area as their retirement destination.

Cultural attractions such as the aforementioned Naismith Memorial Basketball Hall of Fame and Forest Park provide entertaining options close to home, while shopping at the Eastfield Mall serves all your needs from food to fashion. There are plenty of scenic parks such as Riverbend Park along the Connecticut River or Elwell Island Nature Sanctuary for exploring nature and enjoying some fresh air on any given day.

Like any big city, Springfield will have some challenges, but it’s big enough that it’s not a dying city or full of just one demographic which tends to be a problem in some of the northern states.



Best Cities To Retire To In Massachusetts - Retire To Holyoke

A suburb of Springfield, Holyoke has an estimated population of 40,000 permanent residents and is known for its vibrant Latin American culture and historic architecture.  Holyoke is perfect for those retirees looking for the suburban life and want to live close enough to a big city (but not the biggest city).

Holyoke is one of the most affordable places in the state to retire. Home prices tend to be lower in Holyoke than many other parts of the country while amenities like restaurants and entertainment remain accessible within walking distance. Monthly rent averages around $1,100, making it a viable option for retirees who prefer rental housing over home ownership. Healthcare needs can be met with medical facilities such as the Holyoke Medical Center and Providence Behavioral Health Hospital located there.

Retirees in Holyoke have plenty of activities that keep them busy during their free time. The area’s Art District features galleries and performance spaces for those looking to explore their creative interests, or those seeking recreation or outdoor activities can take advantage of several hiking trails and parks nearby including Mountain Park or the Cooley-Dickinson Health Care trails. For shopping enthusiasts, Holyoke malls feature an array of retailers from antique stores to popular department stores providing an enjoyable shopping experience

West Yarmouth

Best Cities To Retire To In Massachusetts - Retire To Massachusetts

Do you dream of retiring to Cape Cod? If so, West Yarmouth is an excellent choice.  Like New Bedford, but a bit more approachable.

Located on the shoreline of Nantucket Sound, West Yarmouth offers picturesque views that are sure to delight. The historic seaside village is home to a number of shops, restaurants, galleries, and other attractions that can be enjoyed year-round. Nearby beaches and marinas offer plenty of outdoor recreation opportunities including sailing, fishing, boating, kayaking, and paddleboarding. There are also two Nature Trails at Mill Pond Conservation Area where you can walk your way through over 400 acres of nature trails for an enjoyable stroll or bicycle ride.

For those looking for convenience without sacrificing quality health care options nearby Cape Cod Hospital has recently expanded its services with a 24/7 emergency room alongside family medicine centers throughout the region. Plus there’s nearby Hyannis which houses the Cape Cod Healthcare Urgent Care Center along with great grocery stores like Stop & Shop & Whole Foods Market shopping options always nearby making this area highly livable.

With amenities such as public transportation in convenient walking distance; affordable housing; entertainment including comedy clubs; whales watch tours through Hyannis Harbor Cruises; free local events like concerts in the park and farmers markets; there’s no shortage of things to do in West Yarmouth! Put all this together with tax benefits available here due to its favorable weather year round makes West Yarmouth one of the best cities to retire too in Massachusetts!


Pittsfield is a potential retirement destination for those seeking an affordable, yet culturally rich area in which to retire. With a cost of living index of around 100, it can provide a retirement experience that is both enjoyable and budget-friendly.

The city is especially known for its stunning views of the Taconic Mountains, its deep appreciation for the arts and its numerous recreational opportunities. Whether you’re looking to explore nature up close or find interesting things to do in town, Pittsfield has something to offer every retiree.

Pitssfield offers retirees excellent health care options at low cost as well. Berkshire Health Systems provides an extensive range of services for senior citizens, such as adult daycare, home care assistance and more. It also has great doctors, specialists and hospitals available for seniors in the area.  The city also proudly supports their Artswalk downtown with an ever-growing series of outdoor sculptures and murals featuring local artists from all sorts of disciplines. In addition to these attractions, there are many hiking trails nearby which offer breathtaking view points along with historic sites and interesting wildlife watching opportunities that are sure to be enjoyable to couples or groups during their visit there.


Best Cities To Retire To In Massachusetts - Retire To Plymouth

Plymouth Massachusetts might be the best city in all of Massachusetts to retire to, because it has over 8 active adult retirement communities (or age restricted communities).  Whether you’re looking for Florida style amenities with mini-villages of Great Island or Pinehills or something smaller, Plymouth has just about everything you’d want in a retirement destination, outside warm winters.   Because of the large population of retirees in Plymouth, the whole county (also named Plymouth) benefits with great health care.

Plymouth feels a bit smaller and less industrial than Springfield but is big enough to satisfy any city lover, and there are plenty of suburbs to choose from if you aren’t locked into specific age restricted type communities.   In addition, Plymouth is only a short drive to the coasts.  If you dream looking down your nose at society, that opportunity is around the corner at the capes.