Best Retirement Spot with Big City Feels: Springfield, Massachusetts

By Ethan Bennett Oct 18, 2025

Experience affordability, entertainment, and tax benefits when you retire in Springfield, Massachusetts - one of the top 50 best places to retire.

Tucked in western Massachusetts, Springfield is ranked sixth among the 50 best places to retire in the U.S. by Travel + Leisure and Investopedia, based on factors like cost of living, entertainment options, and availability of essential services. Offering a big city experience without the associated costs, Springfield brings numerous advantages for retirees.

One of the bonuses of Springfield is that Massachusetts does not levy taxes on Social Security benefits and public pensions. In addition, the state offers a Senior Circuit Breaker Tax Credit - a refundable personal income tax credit available to seniors aged 65 and older who own or rent property in Massachusetts. Despite these benefits, keep in mind that Massachusetts has a high state income tax rate. However, the top rate applies only to individuals with an income exceeding $1,053,750.

Housing in Springfield is also affordable with median home values being $276,300 and median monthly housing costs pegged at $1,309. The state sales tax is just 6.25%, making it one of the more affordable states for shopping.

Springfield is set amidst beautiful landscapes and a rich cultural scene, housing 160 arts and entertainment facilities in Hampden County. Noteworthy points of interest include the Springfield Public Forum, the Quandrangle - a hub of art museums and cultural institutions, and the MassMutual Center. The city is also abundant in parkland and golf courses for outdoor enthusiasts. For retirees valuing walkability, Springfield scores an impressive 88 on the Economic Research Institute’s walk score.

While Springfield's population of more than 155,000 might occasionally pose traffic and parking issues, the city has good public transportation links via bus and train, and is situated close to Bradley International Airport.

Regarding healthcare, Hampden County has as many as 22 hospitals and 683 other healthcare establishments, with Springfield housing award-winning medical centers. The state also exempts prescription medical devices and medications from sales tax and provides home healthcare services for seniors and those with certain disabilities.

In conclusion, retiring in Springfield, Massachusetts offers a balanced blend of city life, tax advantages, recreational opportunities, and affordability. However, prospective retirees should consider that costs mentioned are median figures and personal variables could affect overall affordability.

LEAD STORY