7 Most Hospitable Retirement Towns In Massachusetts
As they start to sail into a calmer part of their lives, many retirees look to small towns as a place to settle down. However, some may fear that they’ll be too cut off from their new neighbors, or that if they take up traveling, they will not feel welcome by an insular populous. However, this fear is often unfounded, as many small towns welcome both visitors and new residents alike. These quieter places often cultivate a cozy atmosphere to attract new faces. Rarely is this truer than in Massachusetts, where small towns treat hospitality as an art form, each using their own unique charms to make folk feel at home no matter their age, making them perfect retirement towns.
Provincetown
Perhaps the most welcoming and inclusive potential retirement town in Massachusetts, Provincetown prides itself on its inclusivity, making it a perfect choice for retirees looking for a place to settle down without being excluded from the action. A well-known artist haven, “Ptown” has been a welcoming place for nearly a century. Located on the northern end of Cape Cod, Provincetown welcomes visitors year after year with its vibrant festivals and events all year round, making it perfect for retirees looking for a holiday home-away-from-home or a permanent home where they can feel free to be themselves. Residents and tourists alike flock to its scenic beaches, such as Race Point Beach, with its luminary landmark lighthouse. To get further out to sea, Dolphin Fleet Whale Watch near-guarantees multiple views of majestic humpback whales. Once they’ve had their share of fun in the sun, retirees can rest and refresh themselves at one of Ptown’s many welcoming restaurants, many of which showcase the diversity Provincetown takes pride in. For example, the Provincetown Portuguese Bakery has been offering authentic Portuguese treats since 1936, making for a warm welcome to start your morning right.
Rockport
Many retirees see their newfound free time as the perfect time to focus on artistic pursuits or find some new hobbies, and a perfect place to start is Rockport. Another Massachusetts artists’ colony with a long history, Rockport has a rather unique claim to fame with ties to both its industrial and artistic history. Known as Motif #1, this unassuming little red fishing shack has been constantly captured on canvas and film by decades-worth of artists. As a result, Rockport welcomes tourists and artists from every corner of the world, putting the town of 5,000 to the test when it comes to hospitality, but Rockport passes with flying colors.
Rockport's many inns and restaurants, like the Sally Webster Inn, set in a 19th-century home on the docks, are open to tourists and new residents alike. Tuck’s Candy and Gifts has been operated by three generations of the Tuck family, and provides traditional, home-made candies just like many retirees would have grown up with. They even offer a candy of the month to help give retirees something sweet to fill their now-open calendars.
Ipswich
Ipswich is famed for its abundance of natural beauty, and this beauty is easily accessible no matter one’s level of activity, making it perfect for retirees who are looking to return to nature at a comfortable pace. With over three centuries of visible history and a serene spot along the Coastal Byway, Ipswich welcomes retirees with open arms and open air, especially at the centerpiece of the Crane Estate, Castle Hill. This storied estate has a colorful and storied past, ranging from its time as a gentleman’s farm in the 1880s to its rebirth as a country estate in the 1920s, complete with a Suart-style mansion built in the Roaring Twenties. Today, Castle Hill serves as a centerpiece to the Crane Estate, an incredibly diverse natural wonderland that includes both Crane Beach and the Crane Wildlife Preserve. Retirees can find something to fit their preferences, whether that’s touring the mansion, its lovely gardens, or the many hiking trails which spring from Castle Hill and spread to the rest of the Crane Estate.
Amherst
With Hampshire County’s largest population, some newly retired seniors may overlook Amherst, but they risk missing out on one of the Bay State’s most well-suited gems. Home to not only the famed poet Emily Dickinson, but three prestigious colleges, Amherst maintains a erudite, poetic feel which makes for a cozy retirement town, especially for academics or retirees looking to try their hand at literary pursuits, genealogical research, or just catching up on their reading. Amherst offers plenty to inspire and intrigue visitors and residents, and when they need something strong or sweet to fuel their pursuits at any hour, Amherst Coffee + Bar has them covered. Located in a historic cinema, Amherst Coffee + bar has kept residents well-lubricated for many years, making it a perfect base camp for exploring Amherst’s vibrant nightlife. A prime location for said nightlife, the Drake offers a variety of performances ranging from live music to comedy, and even local storytelling, meaning it’s a good way to enjoy a variety of entertainment without having to go too far from home.
Sandwich
Another Cape Cod charmer, Sandwich was the first town founded on the Cape, and its long history echoes throughout even into modern days, offering retirees a chance at the classic idyllic New England Village life, complete with the original buildings in some places. Its collection of working museums and historic landmarks gives retirees who are struggling with adapting to a more leisurely lifestyle many opportunities to volunteer and keep their hand on the pulse of industry. A perfect example is the Dexter Grist Mill, a working corn mill where you can even purchase fresh-ground cornmeal in a classic bag, letting seniors reconnect with their family’s roots. If you want something sweeter to keep you busy, the Green Briar Jam Kitchen, also known as the Ida Putnam Jam Kitchen, provides just the thing. Since 1903, Ida Putnam’s jams have been a Cape Cod classic, and visitors to the museum can see these famous jams being made and even learn to make some for themselves in the many cooking classes offered, giving retirees a fun activity to help keep them active.
West Chatham
A prime resort area since the 1800s, West Chatham, a neighborhood in the city of Chatham, is considered by many to be the heart of one of the best places for retired seniors in the entire Bay State. Nestled cozily on the south-eastern side of the Cape, Chatham avoids the crowds while offering easy access to the gorgeous coastlines that draw so many to Cape Cod, as well as other classic New England activities to help keep a retired life flavorful. For example, Cranberry Bog Tours operates on the largest cranberry bog on the Cape, only a short drive away. Operated by Leo and Andrea Cakounes, this nearly twenty-acre farm offers tours year-round and offers farm-fresh cranberries for sale. For those looking for something more substantial but with that familiar New England charm, the Chatham Squire has been serving residents and visitors alike for nearly sixty years. Serving seafood, pub favorites, and creative cocktails, the Squire is a staple of Downtown Chatham, making it easily accessible by West Chatham retirees.
Nantucket
Like the protagonist of Herman Melville’s legendary literary leviathan, Moby Dick, the sea has always called those opening a new chapter in their life, such as the newly retired, and Nantucket has always offered retirees a welcoming shore. With a name meaning “The faraway land” in the language of the Wampanoag tribe who once lived here, Nantucket is an excellent new home for retirees looking to relax and watch the world come and go like the tides. Located on a cozy island roughly fifty miles south of Cape Cod, Nantucket is only an hour away from the mainland via ferry, but also serenely separate from the hecticness of modern life.
Seniors can enjoy their retirement on serene beaches, such as the lovely Brant Point Beach, which has an excellent view of passing ships and lies within walking distance, and even has an excellent spot to wave to friends and family returning to the rush of mundanity, the Brant Point Lighthouse. This gorgeous landmark, having once served to warn ships away from the ship-wrecking shoals, now serves to welcome the ferry as it arrives at the island, and it’s a prime first stop for tourists and a last stop.
Massachusetts’s many small towns contain a treasure trove of potential retirement towns for those seniors looking for fulfillment and rest in this new chapter of their lives. From the many gems of Cape Cod to the wooded wonders of its mainland, the Bay State has something for any retiree, regardless of their level of activity or appetite for adventure. Opportunities to fill their leisure time with fun and excitement, volunteer work, or just good old-fashioned variety. Their New England charm is on full display, including the welcoming atmosphere that makes for countless cozy days exploring the seaside or immersing oneself in Massachusetts’s deep history. Retirees will find a warm welcome in whichever retirement town they find themselves in.
