Planning to retire to New England?

If you are looking to relocate once you retire, New England might be the perfect place for you. The leaves look beautiful in the fall, and the winters are cold and snowy. But besides the mild temperatures most of the year and the beautiful scenery, this is also one of the favorite places for retirees.

Many wonder why this is the case, considering that New England isn’t exactly cheap. High costs, unfavorable tax policies, and the harsh winter don’t make the states in this area the most senior-friendly ones.

For example, in 2024, Vermont and Rhode Island were included in the top 10 states people chose to move into for retirement. In recent years, New England states managed to overcome potential turn-offs, and this attracted a flux of new residents.

So, if you are considering moving here, read on and discover more about the best states and cities you can choose from!

Portland, Maine

This is the biggest city in Maine, and the population keeps increasing year after year. Retirees love this place because it is a city that managed to keep its small-city charm and natural beauty. This is an important aspect because you get all the things a big city can offer while also taking advantage of the beauty of nature.

Portland has a population of 68,000, and of this number, 15% are 65 or older. This makes it a great destination for any senior looking to move to New England. Indeed, the cost of living is about 12.5% above the national average, but many find it a great place because the quality of life is high, and you also have access to breathtaking landscapes and modern amenities.

The average income in Portland is $86,400, which means the local economy is strong. Furthermore, the well-being score is 70 out of 100. As a coastal city, Portland offers you access to many outdoor activities, from kayaking and fishing to simply walking on the shore of the ocean.

Despite the chilly months, Portland’s mix of urban and small-town vibes, paired with the rich cultural scene, makes it a great destination for any retiree who wants to relocate.

Burlington, Vermont

You can find this city between the shores of Lake Champlain and the Green Mountains, and this is one of the favorite locations where retirees choose to relocate. Burlington has a population of 44,700, and 12.1% are aged 65 or older. Yes, this is a small city, but it’s full of personality.

Considering the beautiful nature and the size of this city, you can try to move here if you want to spend time outdoors and also remain connected with your friends and neighbors. The well-being score is 74 out of 100, and this is all due to the eco-conscious community and the abundance of fantastic outdoor areas.

Hiking, biking, kayaking, paddleboarding, and skiing are all at your doorstep. Also, the community is all about suitability. Farmers’ markets and co-ops, or local companies like Seventh Generation, all make this city greener.

But this eco-style way of living has a price. The cost of living is 12.4% above the national average, and if you think about a house, keep in mind that home values in Burlington are around $479,000. Renting is also costing a fortune, and the median price of a rented property is $2,250 per month. Health care and long-term care are expensive as well, and this is not the best thing you can hear if you are struggling to live on your Social Security.

But if you have the money and you like to learn new things, then you might appreciate Burlington’s academic perks. The University of Vermont has many tuition-free classes for state residents aged 65 and older.

Pittsfield, Massachusetts

If the charm of New England stole your heart, but you feel like everything is too expensive to move there, then we are here to tell you that Pittsfield might be the solution. This small city of just under 44,000, which can be found in the heart of the scenic Berkshires, has a special trait that makes it different than other New England cities: the cost of living is 4.1% below the national average.

For the retirement-friendly vibe, all we can say is that 20% of Pittsfield’s population is 65 or older. If you want to find people close to your age, then this is the perfect place!

The average home value is around $263,800, which is a steal compared to the prices you can find in cities like Boston. Here, the price can be more than double! The well-being score is 59. A modest score, but access to nature and cultural opportunities can boost the appeal of this small city.

All in all, Pittsfield is a peaceful place with a slow pace of life, and you have plenty of options when it comes to year-round activities. During the fall, the leaves make a spectacle here with their colors, and during the summer, camping, fishing, and hiking are the main things you can do. Later on, in the winter, skiing in the nearby mountains is a very popular choice.

But if you are not a person who likes outdoor activities, this small city also has the Tanglewood Music Center, home of the Boston Symphony Orchestra, and some well-known museums such as the Clark Art Institute and MASS MoCA.

Wallingford, Connecticut

This place encompasses the spirit of New England with all the sophistication and warmth everybody feels once they enter this area. Wallingford is a wonderful place for any senior who wants to stay active during their golden years.

Here you can find a welcoming community that is perfect for older adults. The cost of living indeed is 9.2% higher than the national average, but this is typical for the state of Connecticut. The truth is that the higher cost is totally worth it, considering the quality of life and access to excellent healthcare. For example, Gaylord Hospital is right in the town, and the senior center is equipped with all the things needed for a good life, from clinics, fitness classes, and social activities to card games and billiards.

If you are interested in cultural activities, Wallingford has the Paul Mellon Arts Center and the Toyota Oakdale Theater. These are the places where concerts and performances take place. Then you also have the public library, a true opportunity for anyone interested in lifelong learning.

The local cuisine is rich, and you have lots of places if you want to eat in the city. For example, Serafino’s Ristorante Italiano and Boggs serve some of the coziest meals in the whole town.

If you want to enjoy a drink while looking at the setting sun, then you should definitely try nearby spots like Paradise Hills Vineyard and Gouveia Vineyard, or the Center Street Brewing Company.

Do you want to learn more about New England and its magic? Check out this amazing guide: Frommer’s New England (Complete Guide)
You should also read more about: 7 Best and Worst States for Retirement in 2025