Beautiful Stage Harbor at Chatham Massachusetts in Cape Cod.

12 Best Towns to Retire in Massachusetts

Part of the New England region of the United States, Massachusetts, is a scenic coastal state full of opportunities. While being the seventh smallest in land area, it is densely populated with amazing people and culture. Add on the state’s intriguing past, outdoor beauty, and great healthcare for an amazing place to settle down. Beckoning people from all over, there are many small towns in Massachusetts perfect for seniors. These towns have the amenities and attractions without the crowded environment for a great retirement.


View of historic building and methodist church in Pittsfield.
View of historic building and Methodist church in Pittsfield. Image credit travelview via Shutterstock

Full of urban charm, Pittsfield is a stunning retreat and the county seat of Berkshire County. With bustling streets and encompassing outdoor scenery, you can enjoy a lively retirement in the town. Head out into the downtown area, and there is no shortage of things to do. History lovers can explore the Berkshire Museum. It has exhibits on zoology, ancient civilizations, and engineering. Or, stop by Barrington Stage Company to catch one of their regular plays, such as Anna in the Tropics or A Little Night Music. With these and dozens of other attractions like the Hancock Shaker Village and Herman Melville’s Arrowhead, you’ll never get bored of life in Pittsfield.

That said, once you step out of the town center, there is a whole new world waiting to appreciate. At the western edge of town, Lake Onata is the perfect place to head out with your mates. Set up along the shore and cast lines to enjoy a relaxing time fishing for dinner. Surrounded by the panoramic Taconic Mountains, you can spend hours here appreciating the picturesque environment.

While the sights are attractive, there are lots of things to consider before retirement. Thankfully, Pittsfield ticks all the boxes. With an affordable median home value of $183,600, buying a home here costs less than half the state average. So, whether you want a small cottage or a large mansion, you can get luxury without the exorbitant price tag. Moreover, with a great local bus system, traveling around town is easy.


Lenox, Massachusetts: The Mount, home of American author Edith Wharton, seen from the formal French flower garden
The Mount, home of American author Edith Wharton in Lenox, Massachusetts.

If Pittsfield sounds a bit too crowded for your liking, the town of Lenox is a reprieve from urban hustle and bustle. Known for its vibrant culture, you’ll find a tight-knit community of 5,000 residents always up for a quick chat or outing. You can spend relaxing evenings in the silent streets of town lined with interesting cultural attractions. For fans of the arts, Tanglewood Theatre and Shakespeare & Company are two amazing theatres with regular shows. From symphonies by James Taylor to plays by William Shakespeare, every day holds an exciting new play or show. Retirees with a knack for reading can spend their time at the Lenox Library. The peaceful place, built in 1815, has everything from old books to new magazines for reading. Even if you’re just out for a stroll, the New England architecture and historic structures create a timeless environment.

While there is no end to the options in Lenox, you’ll be glad to know that there is also no end to the friends you can make. This is because over 37% of Lenox’s population are senior citizens. So, from your neighbors to the people you meet in town, there will be like-minded individuals all over. The town is also home to many natural areas, such as Kennedy Park and Lenox Mountain, which are great places to stay active and fit.

West Springfield

Attendees of the Big E enjoy carnival games in West Springfield, Massachusetts
Attendees of the Big E enjoy carnival games in West Springfield, Massachusetts. Image credit Keith J Finks via Shutterstock

Often listed as one of the best places to live in Massachusetts, West Springfield is an amazing destination for retirees. The town exudes a homely environment with small cafes, restaurants, and shops lining the streets. For example, enjoy a classic “Hamburg” at the White Hut restaurant or spend some time shopping at Holyoke Mall. Thanks to its dense suburban design, you’ll always be within walking distance of a medical center, eatery, or school. Moreover, if you’re planning on an active retired life, there is no shortage of green space and fresh air. Visit Mittineague Park for peaceful nature trails along the beautiful Westfield River. Or, head out for a morning jog at Ashley Reservoir, which provides thick forests and glistening waters. Come here enough, and you might spot the local wildlife, including beavers, turtles, and herons.

From the delicious food to the calming walks, West Springfield is a peaceful location to settle down. Apart from the abundance of amenities, retirees can enjoy great road connectivity via Interstate 91 and US Route 5. Moreover, the city of Springfield is just a few miles away, so you can always head into the larger center for additional services and attractions.


A crowd of people congregate at a recreated New England village in Agawam, Massachusetts.
A crowd of people congregate at a recreated New England village in Agawam, Massachusetts. Image credit James Kirkikis via

Drive south from West Springfield for a few miles, and you’ll reach the vibrant town of Agawam. Nestled along the banks of the Connecticut River, this town boasts natural beauty and towny vibes for a tranquil retirement journey. Drawing in retirees from all over, a hot spot in town is the Crestview Country Club. Featuring an 18-hole championship golf course, one can watch a game or tee off with the locals for fun under the sun. For those of you who aren’t interested in golf, the nearby Robinson State Park is a great alternative to get outdoors. Home to more than 1,000 acres of verdant forests and peaceful waters, enjoy a walk or hike in nature’s allure. Nature aside, retirees can relive their youth at the famous Six Flags New England theme park. Hop on The Joker rollercoaster or attend Fright Fest with your family to have a blast amongst loved ones.

The best part about retirement in Agawam is the high quality of living at affordable prices. With less than 7% of the population living in poverty, the town’s strong economy promotes industries and businesses. So, you can enjoy accessible medical facilities, eateries, and restaurants throughout your retirement. Parallelly, a lower population density compared to nearby cities means you’ll still have the luxury of personal space and time.


Colorful Chatham Lighthouse on the shores of Cape Cod
Colorful Chatham Lighthouse on the shores of Cape Cod.

Once a fishing community, Chatham is an affluent town with about 6,000 residents living along the picturesque Cape Cod. Set up a chair at one of the town’s many beaches to enjoy retired life to the fullest. You can spend hours sunbathing by the calm waves at beaches such as Ridgevale and Harding. Apart from beaches, the town’s 46% of residents over 65 often enjoy the town’s amazing shopping and dining scene. Filled with tourists and locals, Main Street is the place to be if you want to grab a bite, shop, or just enjoy a walk. For the newly retired, the Chatham Home is the perfect store selling home goods to spruce up a retirement home.

While shopping and dining, things can be a bit expensive in Chatham as it is the richest town on Cape Cod. That said, despite a median house value of more than three times the state average, you’ll be getting your money’s worth. A low crime rate of less than half of the national average means you can focus on having a fun time. Along with this, the town’s residential areas are clean, scenic, and home to lovely retirees to mingle with.


Fall foliage with the Greater Amherst, Massachusetts urban landscape in the distance
Fall foliage overlooking the Greater Amherst, Massachusetts.

Escape to Amherst for a lively retirement surrounded by a rich college environment. Home to the flagship campus for multiple institutes, including the University of Massachusetts and Amherst College, entertainment abounds in Amherst. Despite a lower percentage (8%) of the town being over 65, retirees can participate in the town’s abundant opportunities. College campuses and areas are bustling with activities, from concerts and events to boutiques and shops. So, if you don’t mind rubbing shoulders with kids, you can enjoy delicious wine at the Amherst Farm Winery or fresh fruits from the Farmer’s Market.

Apart from this, the town’s historical attractions are more popular with senior citizens, with options such as the Emily Dickinson Museum or Yiddish Book Center. The 1813 Emily Dickinson Museum is in the famous poet’s childhood home, and you can spend hours taking in the preserved decor. Similarly, the Yiddish Book Center is a preservation of the Yiddish language with unique reading material throughout.

Furthermore, the prominent educational structure makes Amherst a great place for families to live. Seniors can feel confident in their neighborhood's commitment to education because there are many teachers and professors in town. Combine this with the rail and air connectivity via the nearby town of Northampton, and you have yourself a retirement town in Massachusetts.


Dunn state park, Gardner, Massachusetts.
Dunn state park, Gardner, Massachusetts.

An hour east of Amherst, Gardner is an affordable town perfect for people who want to settle down. With a median home price of $200,000, which is less than half the state average, getting your dream retirement home doesn’t involve breaking the bank. Use the money you save to fill out your home with Gardner’s beautiful furniture options. Nicknamed the "Furniture Capital of New England," stores such as Big Lots and LaChance Interiors Inc. are ideal for high-quality mattresses, sofas, cupboards, and more. Once you’ve set up your home, head over to the West Gardner Square Historic District, where you’ll find many of the local retirees. Boasting dozens of structures, such as the Garbose Building and Heywood-Wakefield Company Complex, it is a glimpse into the town’s past. Apart from the historic buildings, shops, and eateries keep, the area is upbeat and great for an outing. You can also enjoy outdoor pursuits at the Dunn State Park in town. Whether it is fishing, hiking, or a picnic with family, one can always appreciate the thick forests and glistening Dunn Pond.

Along with the economic benefit of retirement in Gardner, the town is also quite safe. A noticeably low crime rate ranks it among the safest towns in Massachusetts. If you ever need medical care, Heywood Hospital has 200 doctors and over 100 beds for advanced healthcare. So, all you need to focus on is building your dream home in Gardner.


Scargo Lake fresh water kettle pond Dennis Massachusetts Cape Cod
Scargo Lake, fresh water kettle pond Dennis, Massachusetts, Cape Cod.

Dennis is another scenic town situated along the beautiful Cape Cod. Comprised of five villages, the small town has everything from waterside views to fresh seafood. Testament to the lovely Atlantic coastline, Dennis is full of retirees looking to experience a happy retirement. With 35% of the 15,000 residents over 65 years old, the town is full of peaceful vibes. You can see most of these senior citizens relaxing along Mayflower Beach for its calm waters and white sand. Stay back till sunset to witness the sun’s hypnotic orange glow bounce off the meandering waves of Cape Cod. West Dennis Beach and Corporation Beach are also enjoyable places with many activities available. From a creative perspective, retirees can appreciate the arts by checking out the local art galleries and museums. From sculptures at the Cape Cod Museum of Art to pottery at the Scargo Stoneware Pottery & Art Gallery, one can learn from the best.

While you’ll surely have a lot to do with your new hobbies, Dennis also has amazing amenities for retirement. As it is a resort town, there are endless options when it comes to lodging. From motels to all-inclusive resorts, your family will have no trouble finding a place to stay when they come to visit.


Bass River in Yarmouth, Cape Cod.
Bass River in Yarmouth, Cape Cod.

Yarmouth is a quaint coastal town located within Cape Cod. To this end, it provides all the scenic views along with great connectivity to central Massachusetts. Home to a wonderful bunch of 25,000 residents, Yarmouth has a positive environment that retirees can appreciate. You’ll find most of the local seniors taking in the town’s 400-year-old history. Settled in 1639 as part of the Plymouth Colony, the town has a long history. Learn about the eventful past at sites like Old King’s Highway, Captain’s Mile, and the Judah Baker Windmill. These establishments are hundreds of years old and provide a trip back in time with interesting stories. Apart from the usual cultural site, Yarmouth also features the stunning Whydah Pirate Museum. Popular with local retirees and families alike, it showcases the Whydah Gally, the world’s first pirate shipwreck. The museum also has treasure, silver coins, and pirate weapons on display, which makes it a great place to visit with your loved ones. That said, the coastline is always present for you to stretch out those muscles with the company of soothing waves.

Drawing in retired individuals from all over with its allure, Yarmouth has various features that make it an ideal destination. To begin with, the town has lots of great retirement communities. The staff is welcoming, and the residents are friendly. Thirwood Palace and Maplewood at Mayflower Place are excellent choices for retirees. A reasonable climate with average humidity makes it easy to understand why Yarmouth is a popular community for retirees.


View of buildings in downtown Northampton, Massachusetts
Downtown Northampton, Massachusetts.

Similar to Yarmouth, Northampton is a renowned retirement destination for history and culture enthusiasts. The county seat of Hampshire County, retirees can be at ease surrounded by urban amenities and fun activities. Watch a riveting play at the Academy of Music Theatre with famous artists and interesting scripts to keep you hooked. Experience a more silent environment at the Smith College Museum of Art, which boasts over 25,000 works of art from global artists. After taking in the cultural appeal, stop by the Thornes Marketplace shopping mall to grab anything you may need from kitchen supplies to books.

With so much to offer, Northampton does cost a bit more than other towns on this list, with a median home value of $341,000. Despite the expense, it is an ideal place for seniors thanks to the positive environment and array of facilities. From a medical perspective, the Cooley Dickinson Hospital is an advanced center with emergency and urgent care available. Similarly, plenty of colleges, such as Smith College are set up in town creating a positive educational vibe that promotes growth and prosperity.


Aerial view of downtown Wayland, Massachusetts.
Downtown Wayland, Massachusetts.

The small town in Middlesex County is perfect for retirees looking to live in peaceful surroundings. A mix of history and nature opens up a range of opportunities that anyone can enjoy. To keep in touch with the outdoors, Hamlen Woods is ideal for passive recreation. Seniors flock to this area to experience its beautiful wildlife and mystical allure, perfect for a waterside stroll. If waterside isn’t enough, one can head out on a kayak or canoe at Cochituate State Park for an enjoyable evening with family. In addition to these outdoor retreats, Wayland is a great place to settle down with family. Places like Wayland Town Beach are sure to be a blast for the little ones at home with volleyball, basketball, and a snack bar. On the other hand, if you’re out alone, the Spellman Museum and Wayland Free Public Library are hotspots bustling with seniors and rich history.

Although Wayland comes with a high price tag, an extremely low crime rate makes it a soothing retreat. From your neighbors to the people you meet, you can rest assured that everyone will be friendly and helpful. With an average of 2.9 people per household, Wayland houses many families, so you can also live here with your loved ones to cut on the cost of housing.


Massachusetts, Elizabeth Islands, Cuttyhunk Island, Gosnold.
Massachusetts, Elizabeth Islands, Cuttyhunk Island, Gosnold.

By far one of the smallest retirement town options, Gosnold is a reprieve from urban hustle and bustle. The town offers a secluded environment situated on the Elizabeth Islands in Dukes County. Here, retirees can relax along the waters with the town’s other 70 residents. As the median age is 61, the majority are seniors, so you’ll always be around like-minded people up for a fun day out. Sunbathing along West Beach, where the white sand and endless waters provide a picturesque locale, is popular. One can also rent a boat to take in the stunning waves firsthand. As it is an island town, ferries are the primary mode of transport for traveling to the mainland. That said, if you prefer being away from crowded places, this place ticks all the boxes for your retirement.

Whether it is a lively town full of culture or a secluded natural abode, Massachusetts has an array of amazing retirement destinations. These towns offer a break from the stress of urban life while still having access to the amenities. So, you can sit back and appreciate retired life in one of these amazing Massachusetts small towns.

  1. Home
  2. Places
  3. Cities
  4. 12 Best Towns to Retire in Massachusetts

More in Places