Best Places to Retire to Experience New England Charm

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Fall colors

If you’re looking for a small-town vibe with abundant open green spaces, quaint farms, scenic coastlines, and majestic mountains then you’ll want to check out the New England region.

This region includes Massachusetts, New Hampshire, Vermont, Rhode Island, Maine, and Connecticut and offers a great combination of Colonial-era charm that’s steeped in history with an eclectic mix of contemporary flair.

And with a four-season climate, you can witness the colorful changes between each season while enjoying the beautiful outdoor environment. So if you’re looking to experience quintessential New England charm in retirement then check out these places below:

Lewiston, ME

This tranquil town along the Androscoggin River, and just 30 miles north of Portland, not only attracts artists and nature lovers but also retirees, which make up a high percentage of the local population. Lewiston is known for its average cost of living and affordable housing within active adult communities like Apple Valley Estates.

It’s also popular for having inexpensive studio spaces that draw in retirees who are artistically inclined. Most of the studio spaces are located in 19th-century buildings with high ceilings or are redeveloped former mill buildings. Cultural offerings are abundant in Lewiston and include Bates College’s large art museum, Olin Arts Center, a downtown arts district, several theater companies, and the public library that hosts concerts and festivals in its Marsden Hartley Cultural Center.

For the outdoor enthusiast, access to the Androscoggin River connects to numerous lakes and streams that provide plenty of options for water activities like fishing and boating. Lewiston’s crime rate is also very low, making this small Maine town a safe and welcoming place to reside.

Springfield, MA

Although Springfield, MA is geographically small, it sure does pack a big punch. This charming New England town has a vibrant nightlife scene that allows retirees to feel young at heart. Springfield has a long list of lounges, restaurants, pubs, museums, art galleries, and historical sites that give this quaint town an energetic boost. Retirees can visit five world-class museums on Chestnut Street, check out Emily Dickinson’s home in Amherst, or attend a live performance at Springfield Symphony Hall on Court Street.

Situated in the heart of Pioneer Valley also gives Springfield a charming village vibe that provides endless options for outdoor recreation. Active adults can explore a preserved pioneer village, hike or horseback ride through Mount Holyoke Range State Park, or boat and fish along the Connecticut River.

During the winter season, they can visit plenty of ski resorts in the vicinity for alpine skiing in the valley. Active adults can also find reasonably priced homes within a 55-plus community like The Gardens of Wilbraham that’s just 20 minutes away from downtown Springfield.

Newport County, RI

Southern Rhode Island’s Newport County area is a picturesque retirement destination for active adults looking to stay close to family and friends while experiencing a four-season climate and a New England lifestyle. The area is ripe with art, culture, and history as well as scenic coastlines and countryside.

This small area features charming active adult communities that provide quiet neighborhood settings with resort-style amenities. Newport County also has a wide selection of entertainment and attractions that make for an active and exciting lifestyle for many retirees.

They can tour the historic Newport mansions and witness the grandeur of these luxurious and perfectly preserved fabled estates from a bygone era. Newport County offers more than 400 miles of coastlines and majestic sandy beaches that are the perfect place to relax and sunbathe during the summer season. In the city of Newport, retirees can set sail on their yacht to visit other coastal towns or dock at some of the best marinas in the area.

Plymouth, MA

Retirees looking for a waterfront retirement destination but don’t want to spend a fortune in areas like Cape Cod may have a better chance in Plymouth, MA. The city has beautiful beaches like Plymouth Long Beach, Whitehorse Beach, and Scusset Beach.

The coastline is also ideal for whale watching and fishing during the summer months. Known for being the site of the Pilgrims’ landing in America, Plymouth is nicknamed “America’s Hometown” and has a great selection of historical sites and museums that cater to retirees and history buffs.

They can visit the indoor/outdoor Plimoth Plantation museum that houses a full-size replica of the Mayflower or the Pilgrim Hall Museum, the oldest public museum in the nation that features the artifacts of hundreds of Pilgrims.

In addition to the historical attractions, retirees can enjoy a variety of cultural offerings like the Philharmonic Symphony Orchestra, waterfront concerts, art gallery exhibits, and music festivals. Plymouth is conveniently situated in a central location that is home to numerous 55+ communities and it’s also just an hour’s drive to Boston for big-city entertainment.

Concord, NH

Concord, New Hampshire offers retirees a combination of New England charm with a host of cultural activities. This capital city is known to be a welcoming and friendly locale that typically attracts retirees.

The small-town atmosphere also allows for residents to mingle at events throughout the year. The Capitol Center for the Arts regularly hosts live performances and screens broadcasts of the Metropolitan Opera and National Theatre Live productions. The community also features art walks, art galleries, concert series, and musical performances.

Concord is known for its downtown farmers market during the summer months, offering fresh local produce that draws in large crowds. Concord’s central location within Southern New Hampshire gives residents a great selection of active adult communities within the vicinity such as The Nevins in Londonderry. Retirees can also drive to nearby cities like Manchester that’s just 30 minutes away or Boston that can be reached in about an hour.

Middletown, CT

Middletown is home to Wesleyan University, which provides residents with a small, college-town vibe. It has some of the best cultural offerings as well as shopping and dining options thanks to its vibrant central business district.

Residents have a rich lineup of local shops and restaurants on its main strip as well as the Center for the Arts at Wesleyan that offers dozens of art, theater, and music events throughout the year. Although Connecticut is one of the most expensive states to live in, retirees may be able to find reasonably priced homes in Middletown.

The area features active adult communities like Sonoma Woods, which is a quaint 55+ neighborhood with homes priced from the high $200s to the high $300s. Retirees also have plenty of ways to stay active and involved in the community thanks to its social and close-knit atmosphere. Residents typically spend their time volunteering at local arts organizations or joining the AARP group.

Can you spot the $207,744 difference between these identical homes?

Financing is the difference!

Get the details in The 62+ Loan Homebuyers Guide.

55places Mortgage is a joint venture between Mutual of Omaha Mortgage and 55places.com.
Details here.

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I agree that 55places and its affiliates, partner providers or agents may call, text, or email me about my inquiry, which may be made with automated means. I understand that my consent is not a prerequisite for buying a property. I may revoke my consent at any time by contacting optout@55places.com. Message/data rates may apply. I also agree to 55places.com’s Privacy Policy and Terms of Use.

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