6 Massachusetts Cities That Are Perfect for Retirement

In the heart of New England lies the large state of Massachusetts. Massachusetts is home to great cities like Boston and Springfield, but also offers great small-town country living. Surrounded by pristine forests, rich culture, and friendly locals, Massachusetts is home to plenty of great cities to retire to.

West Chatham

Aerial view of Chatham, Massachusetts

Just an hour and a half south of Boston lies the sleepy coastal town of West Chatham. Home to about 1,500 people, life in West Chatham is leisurely, which is exactly what the locals like. Being right on the sea, it should come as no surprise that there is a thriving community of fishermen and sailors there.

There are a surprising number of amenities in the city. To the north of the city is the great Eastward Ho golf course. Suitable for both beginners and experienced players, Eastward Ho has a variety of holes with varying levels of difficulty.

West Chatham even has its own airport. Although Chatham Municipal Airport is small, it offers residents the opportunity to explore the surrounding area on guided tours and even offers lessons in flying airplanes. However, living in such an ideal place is not cheap. The average home here costs about $605,000.

North Falmouth

West Falmouth Market, West Falmouth, Massachusetts.  Image credit John Phelan via Wikimedia Commons
West Falmouth Market, West Falmouth, Massachusetts. Image credit John Phelan via Wikimedia Commons

Just an hour west of Chatham is another coastal town called North Falmouth. North Falmouth has about twice the population of Chatham, but is still just as relaxing and leisurely. The locals here are very friendly, but remain rather reserved.

The town itself offers plenty of shopping opportunities and is equipped with a fantastic promenade that offers perfect views of the sea. There are also numerous parks and hiking trails that wind through the rolling forests.

Most of the city's residents spend most of their time either on Magensatt Beach or out on the water. At least when the weather permits. Buying a house here is quite expensive. The average home costs about $837,000. That being said, North Falmouth is definitely worth a look if it's in your price range.

Manchester by the Sea

Marina in Manchester-by-the-Sea, Massachusetts.
Marina in Manchester-by-the-Sea, Massachusetts.

One of the better-known small towns in Massachusetts, Manchester-by-the-Sea is New England in the truest sense of the word. Manchester-by-the-Sea's old town center is full of charm and history and is full of interesting shops and businesses, usually based in buildings that are over 100 years old.

Manchester-by-the-Sea is connected to a railroad that runs from Boston to Newburyport in the north. This makes traveling both to the big city and to other cities relatively easy. Especially if you don't drive or have access to a vehicle.

There are also great community restaurants and coffee shops like Boo Bird, Cala's and Laughing Gull Cafe. Golf also plays a big role in the city. Essex Country Club is a world-class facility that is home to world-class tennis courts as well as one of the best golf courses in the state. The high standard of living here comes at a price. The average house costs 1.2 million.


Red Lion Inn in Stockbridge, Massachusetts, USA.
Red Lion Inn in Stockbridge, Massachusetts, USA.

Located in western Massachusetts, the small town of Stockbridge is a great candidate for retirement. With a population of around 2,000 residents, anyone who moves to Stockbridge is guaranteed a quiet and peaceful life.

Stockbridge is surrounded by small woodlands and farmland. This picturesque town has numerous hiking trails running along its borders and is great for short walks or long hikes. You are sure to encounter some of the local wildlife along the way.

The Stockbridge Gold Club and the Berkshire Botanical Gardens are probably the city's two biggest attractions. They are both great places to relax and unwind. Settling in Stockbridge is relatively affordable, with the average home costing around $670,000.


Aerial view of historic downtown Newburyport.
Aerial view of historic downtown Newburyport.

Newburyport is certainly one of the larger small cities. It has a population of around 18,000 people. The larger size may deter some who want to enjoy the absolute peace and quiet of country life, but it also offers the appeal of having all the bells and whistles of a city without all the noise and crime caused by traffic jams.

There is plenty to do in Newburyport. Often just a short walk along the city's beautiful seafront promenade is enough to convince someone to move here. The Market Square Historic District is one of the standout attractions. This part of the Old Town is full of charm and intrigue as its red brick shops and cobbled streets are sure to keep visitors coming back for more.

The infrastructure is also surprisingly robust. Newburyport has its own hospital, Anna Jaques, which many retirees appreciate. It is also connected to the railway line that runs south in Boston and Manchester on the Sea. The average home in Newburyport costs $792,000.


Downtown Orange, Massachusetts.
Downtown Orange, Massachusetts.

The small town of Orange, located in northern Massachusetts, is a criminally underrated part of the state. Home to around 7,500 people, Orange is a great place to retire if you want to live in a hard-nosed, working-class town that also has access to the finer things in life.

Orange has pretty much everything you could want in a retirement city. Orange is a relatively close-knit community known for its openness and hospitality to newcomers. In the summer, the city comes to life and flows onto the banks of the Millers River, which flows through the city center.

The old school rustic architecture from decades past can still be seen and has been well maintained in every respect. Orange even has its own airport in the city and there are numerous campsites and parks around the outskirts. Life here is also relatively cheap. The average home in Orange costs $282,000.


It's no wonder Massachusetts is often at the top of retirees' lists. The climate may be a bit cold in the winter, but the classic New England charm is hard to beat. The region's community, culture and history are like nowhere else in the United States.

Anna Harden

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